Skip to main content
Log in

Synthesis of partially hydrogenated 1,3,5-thiadiazines by Mannich reaction

  • R E V I E W
  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

We offer a systematic and generalized review of literature data over the previous 10 years regarding the synthesis of monocyclic and condensed 1,3,5-thiadiazine derivatives under the conditions of Mannich reaction.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Figure 1
Figure 2
Figure 3
Figure 4
Figure 5
Figure 6
Figure 7

Similar content being viewed by others

Notes

  1. Dotsenko, V. V.; Frolov, K. A.; Krivokolysko, S. G.; Pekhtereva, T. M.; Suykov, S. Yu.; Papayanina, E. S.; Dmitrienko, A. O.; Bushmarinov, I. S., unpublished results.

References

  1. Würbach, G.; Klöcking, H. P. Pharmazie 1973, 28, 254.

    Google Scholar 

  2. Ozçelik, A. B.; Ersan, S.; Ural, A. U.; Ozkan, S.; Ertan, M. Arzneim. Forsch. 2007, 57, 554.

    Google Scholar 

  3. Katiyar, D.; Tiwari, V. K.; Tripathi, R. P.; Srivastava, A.; Chaturvedi, V.; Srivastava, R.; Srivastavа, B. S. Bioorg. Med. Chem. 2003, 11, 4369.

    Article  CAS  Google Scholar 

  4. Aboul-Fadl, T.; Hassanin, K. Pharmazie 1999,54, 244.

    CAS  Google Scholar 

  5. Sriram, D.; Mallika, K. J.; Yogeeswari, P. Sci. Pharm. 2004, 72, 35.

    CAS  Google Scholar 

  6. 1,3,5-Thiadiazine-2-thione with bactericidal and antitumor action: (а) El Bialy, S. A. A.; Abdelal, A. M.; El-Shorbagi, A.-N.; Kheira, S. M. M. Arch. Pharm. Chem. Life Sci. 2005, 338, 38. (b) Rieche, A.; Hilgetag, G.; Martini, A.; Nejedly, O.; Schlegel, J. Arch. Pharm. Ber. Dtsch. Pharm. Ges. 1960, 293, 957. (c) El-Shorbagi, A.-N. Arch. Pharm. Pharm. Med. Chem. 2000, 333, 281. (d) Hussein, M. A.; El-Shorbagi, A.-N.; Khallil, A.-R. Arch. Pharm. Pharm. Med. Chem. 2001, 334, 305. (e) Ertan, M.; Tayhan, A. B.; Yulug, N. Arch. Pharm. 1990, 323, 605. (f) Saraç, S.; Ertan, M; Balkan, A.; Yulug, N. Arch. Pharm. 1991, 324, 449. (g) Aboul-Fadl, T.; Khallil, A.-R. Arzneim. Forsch. 2003, 53, 526. (h) Ertan, M; Bilgin, A. A.; Palaska, E; Yulug, N. Arzneim. Forsch. 1992, 42, 160. (i) Ertan, M.; Sarac, S.; Yulug, N. Arzneim. Forsch. 1990, 40, 790. (j) Balkan, A.; Ertan, M.; Sarac, S.; Yulug, N. Arzneim. Forsch. 1990, 40, 1246. (k) Ertan, M.; Ayyildiz, H. G.; Yulug, N. Arzneim. Forsch. 1991, 41, 1182. (l) Ilhan, E.; Capan, G.; Ergenc, N.; Uzun, M.; Kiraz, M.; Kaya, D. Farmaco 1995, 50, 787. (m) Chen, G. Q.; Zou, J. X.; Song, X. Y.; Li, Y. L. Yao Xue Xue Bao 1996, 31, 425 [in Chinese]. (n) Hussein, M. A.; Hashem, M. Arch. Pharm. Chem. Life Sci. 2008, 341, 370.

  7. Schorr, M.; Durckheimer, W.; Klatt, P.; Lammler, G.; Nesemann, G.; Schrinner, E. Arzneim. Forsch. 1969, 19, 1807.

    CAS  Google Scholar 

  8. 1,3,5-Thiadiazine-2-thione with anticancer and antitumor action: (а) Pérez, R.; Rodríguez, H.; Pérez, E.; Suárez, M.; Reyes, O.; González, L. J.; López de Cerain, A.; Ezpelata, O.; Pérez, C.; Ochoa, C.Arzneim. Forsch. 2000, 50, 854. (b) Carrasco, R.; Padrón, J. A.; Pérez, R.; Rodríguez, H.; Suárez, M.; Ochoa, C. J. Pharm. Pharm. Sci. 2005, 8, 586. (с) Chen, G.; Han, K.; Xu, X.; Du, X.; Zhang, Z.; Tang, J.; Shi, M.; Wang, M.; Li, J.; Cao, B.; Mao, X. Br. J. Cancer 2014, 110, 63. (d) Radwan, A. A.; Aboul-Fadl, T.; Al-Dhfyan, A.; Abdel-Mageeda, W. M. Asian J. Chem. 2014, 26, 8145.

  9. Klinger, W.; Kersten, L. Acta Biol. Med. Ger. 1964, 13, 574.

    CAS  Google Scholar 

  10. 1,3,5-Thiadiazine-2-thione with antifungal action: (a) Wurbach, G. Dermatol. Monatsschr. 1971, 157, 239. (b) Manohar, V.; Narasimha Murthy, S. V. K.; Sirsi, M.; Ramananda Rao, G.; Narasimha Rao, P. L. J. Pharm. Sci. 1975, 64, 164.

  11. (a) Meinhof, W. Z. Haut. Geschlechtskr. 1962, 33, 124. (b) Meinhof, W.; Jannasch, G. Z. Haut. Geschlechtskr. 1963, 34, 172. (c) Paldrok, H. Sven. Lakartidn. 1964, 61, 2922. (d) Weuffen, W. Mykosen. 1968, 11, 33. (e) Hänel, H.; Raether, W.; Dittmar, W. Ann. New York Acad. Sci. 1988, 544, 329. (f) Von Krempl-Lamprecht, L. Mycoses 1966, 9, 11.

  12. (a) El-Shorbagi, A.-N. Eur. J. Med. Chem. 1994, 29, 11. (b) Aboul-Fadl, T.; El-Shorbagi, A. Eur. J. Med. Chem. 1996, 31, 165. (c) Alfaro-Lopez, J.; Okayama, T.; Hosohata, K.; Davis, P.; Porreca, F.; Yamamura, H. I.; Hruby V. J. J. Med. Chem. 1999, 42, 5359. (d) Abd-Elrahman, M. I.; Ahmed, M. O.; Ahmed, S. M.; Aboul-Fadl, T.; El-Shorbagi, A. Biophys. Chem. 2002, 97, 113.

  13. El-Shorbagi, A.-N.; Tarazia, H.; Semreen, M.; Hayallah, A. Int. J. Pharma Sci. Res. 2014, 5, 460.

    CAS  Google Scholar 

  14. Antiprotozoal thiadiazine: (а) Monzote Fidalgo, L.; Montalvo Álvarez, A. M.; Fonseca Geigel, L.; Pérez Pineiro, R.; Suárez Navarro, M.; Rodríguez Cabrera, H. Mem. Inst. Oswaldo Cruz 2004, 99, 329. (b) Muelas, S.; Suárez, M.; Pérez, R.; Rodríguez, H.; Ochoa, C.; Escario, J. A.; Gómez-Barrio, A. Mem. Inst. Oswaldo Cruz 2002, 97, 269. (с) Monzote, L.; Montalvo, A. M.; Fonseca, L.; Pérez, R.; Suárez, M.; Rodríguez, H. Arzneim. Forsch. 2005, 55, 232. (d) Monzote Hidalgo, L.; Montalvo Álvarez, A. M.; Fonseca Géigel, L.; Pérez Pineiro, R.; Suárez Navarro, M.; Rodríguez Cabrera, H. Rev. Cubana Med. Trop. 2006, 58, 25. (e) Coro, J.; Pérez, R.; Rodríguez, H.; Suárez, M.; Vega, C.; Rolón, M.; Montero, D.; Nogal, J. J.; Gómez-Barrio, A. Bioorg. Med. Chem. 2005, 13, 3413. (f) Coro, J.; Atherton, R.; Little, S.; Wharton, H.; Yardley, V.; Alvarez, A.; Súarez, M.; Pérez, R.; Rodríguez, H. Bioorg. Med. Chem. Lett. 2006, 16, 1312.

  15. Coro Bermello, J.; Pérez Piñeiro, R.; Monzote Fidalgo, L.; Rodríguez Cabrera, H.; Suárez Navarro, M. Open Med. Chem. J. 2011, 5, 51.

    Article  Google Scholar 

  16. Synthesis and biological activity of thiazone: (a) Goksøyr, J. Acta Chem. Scand. 1964, 18, 1341. (b) Peluso, M.; Bolognesi, C.; Munnia, A.; Landini, E.; Parodi, S. Environ. Mol. Mutagen. 1998, 32, 179 and references therein. (с) Papavizas, G. C.; Lewis, J. A. Phytopathology 1972, 62, 417. (d) Barnard, A. J.; Hornby, D. J. Agric. Sci. 1982, 98, 7. (e) Fu, C. H.; Hu, B. Y.; Chang, T. T.; Hsueh, K. L.; Hsu, W. T. Pest. Manage. Sci. 2012, 68, 959. (f) Mao, L.; Yan, D.; Wang, Q.; Li, Y.; Ouyang, C.; Liu, P.; Shen, J.; Guo, M.; Cao, A. J. Agric. Food Chem. 2014, 62, 4864.

  17. The Pesticide Manual Incorporating the Agrochemical Handbook, 11th ed., Tomlin, C., Ed.; Crop Protection Publications, 1997, p. 279.

  18. Evaluation of Methyl Isothiocyanate as a Toxic Air Contaminant. Part A – Environmental Fate by Pamela C. Wales. Technical report, California Environmental Protection Agency, Sacramento, California, 2002, p. 42. Avail. URL: http://www.cdpr.ca.gov/docs/emon/pubs/mitc/augfinl02/augparta.pdf

  19. Thiazone destruction and pesticidal effect: (a) Munnecke, D. E. Phytopathology 1963, 53, 1140. (b) Munnecke, D. E.; Martin, J. P. Phytopathology 1964, 54, 941. (c) Subramanian, P.; Teesch, L.; Thorne, P. S. Environ. Toxic. Chem. 1996, 15, 503. (d) Morrell, J. J.; Sexton, C. M.; Lebow, S. Wood Fiber Sci. 1988, 20, 422. (e) Lam, W. W.; Kim, J. H.; Sparks, S. E.; Quistad, G. B.; Casida, J. E. J. Agric. Food Chem. 1993, 41, 1497. (f) Drescher, N.; Otto, S. Residue Rev. 1968, 23, 49.

  20. Babaeva, R. I. Med. Parasitol. and Parasitic Diseases 1989, (2), 25.

  21. A World Compendium. The Pesticide Manual. Sixteenth Edition. Supplementary Entries – Extended, MacBean, C., Ed.; BCPC (British Crop Production Council), 2012, p. 386. Avail. URL: http://bcpcdata.com/_assets/files/PM16-supplementary-BCPC.pdf

  22. Brief review on Buprofezin: Kanno, H. Pure Appl. Chem. 1987, 59, 1027.

  23. Evaluation of Fully Approved or Provisionally Approved Products. Evaluation on: BUPROFEZIN. Technical report, Pesticides Safety Directorate, UK, 1993. Avail. URL: http://www.pesticides.gov.uk/Resources/CRD/ACP/081_buprofezin.pdf

  24. Merzendorfer, H. J. Comp. Physiol. B 2006, 176, 1 and references therein.

  25. Recent study of Buprofezin bioactivity: (а) James, D. G. J. Econ. Entomol. 2004, 97, 900. (b) Das, C.; Rov, S.; Pal, R.; Kole, K.; Сhowdhury, A. Bull. Environ. Contam. Toxicol. 2004, 72, 307. (с) Wang, Y.; Gao, C.; Xu, Zh.; Zhu, Y. C.; Zhang, J.; Li, W.; Dai, D.; Lin, Y.; Zhou, W.; Shen, J. Pest. Manag. Sci. 2008, 64, 1050. (d) Nasr, H. M.; Badawy, M. E. I.; Rabea, E. I. Pestic. Biochem. Physiol. 2010, 98, 198. (e) Cabra, S.; Garcia, P.; Soares, A. O. Biocontrol Sci. Techn. 2008, 18, 307.

  26. Uchida, M.; Izawa, Y.; Sugimoto, T. Pestic. Biochem. Physiol. 1987, 27, 71.

    Article  CAS  Google Scholar 

  27. Cottage, E. L. A.; Gunning, R. V. J. Mol. Neurosci. 2006, 30, 39.

    Article  CAS  Google Scholar 

  28. Synthesis and bioactivity of NIP-200: (a) Sakamoto, K.; Yamauchi, M.; Nakayama, S.; Tsuruzoe, N.; Sakashita, M.; Fujikawa, Y. Nippon Yakurigaku Zasshi 1987, 90(4), 187. (b) Sakashita, M.; Nakayama, S.; Kitahara, M.; Tsuruzoe, N.; Oguchi, K. Nihon Yakurigaku Zasshi 1992, 99(1), 37. (c) Sakashita, M.; Toyoda, K.; Kitahara, M.; Tsuruzoe, N.; Nakayama, S.; Oguchi, K. Jpn. J. Pharmacol. 1993, 62(1), 87.

  29. Kagabu, S.; Murata, N.; Hibino, R.; Hanzawa, M.; Nishimura, K. J. Pestic. Sci. 2005, 30(2), 111.

    Article  CAS  Google Scholar 

  30. 2,4,6-Trimethylperhydro-1,3,5-thiadiazine as meat aroma component: (а) Kawai, T.; Irie, M.; Sakaguchi, M. J. Agric. Food Chem. 1985, 33, 393. (b) Zhang, Y.; Chien, M.; Ho, C. T. J. Agric. Food Chem. 1988, 36, 992. (c) Zhang, Y.; Ho, C. T. J. Agric. Food Chem. 1989, 37, 1016.

  31. Pyrazolothiadiazine as fungicides: (a) Mares, D.; Romagnoli, C.; Andreotti, E.; Forlani, G.; Guccione, S.; Vicentini, C. B. Mycol. Res. 2006, 110, 686. (b) Mares, D.; Romagnoli, C.; Vicentini, C. B.; Sacchetti, G.; Bruni, A. Microbios 1996, 86 (348), 185. (c) Vicentini, C. B.; Forlani, G.; Manfrini, M.; Romagnoli, C.; Mares, D. J. Agric. Food Chem. 2002, 50, 4839.

  32. Pyrazolothiadiazine as inhibitors of photosynthetic transport of electrons: (a) Vicentini, C. B.; Mares, D.; Tartari, A.; Manfrini, M.; Forlani, G. J. Agric. Food Chem. 2004, 52, 1898. (b) Vicentini, C. B.; Guccione, S.; Giurato, L.; Ciaccio, R.; Mares, D.; Forlani, G. J. Agric. Food Chem. 2005, 53, 3848.

  33. Osolodkin, D. I.; Kozlovskaya, L. I.; Dueva, E. V.; Dotsenko, V. V.; Rogova, Yu. V.; Frolov, K. A.; Krivokolysko, S. G.; Romanova, E. G.; Morozov, A. S.; Karganova, G. G.; Palyulin, V. A.; Pentkovski, V. M.; Zefirov, N. S. ACS Med. Chem. Lett. 2013, 4, 869.

    Article  CAS  Google Scholar 

  34. Reviews on the chemistry of 1,3,5-thiadiazines: (а) Moody, C. J. In Comprehensive Heterocyclic Chemistry, Katritzky, A. R.; Rees, C. W., Eds.; Pergamon Press: Oxford, 1984, vol. 3, p. 1039. (b) Smalley, R. K. In Comprehensive Heterocyclic Chemistry II, Boulton, A. J., Ed.; Elsevier: Oxford, 1996, vol. 6, p. 783. (c) Shobana, N.; Farid, P. In Comprehensive Heterocyclic Chemistry III, Katritzky, A. R.; Ramsden, C. A.; Scriven, E. F. V.; Taylor, R. J. K. (Eds.); Elsevier: Oxford, 2008, vol. 9, p. 457.

  35. Rodriguez, H.; Suárez, M.; Albericio, F. Molecules 2012, 17, 7612.

    Article  CAS  Google Scholar 

  36. Rodriguez-Fernández, E.; Manzano, J. L.; Benito, J. J.; Hermosa, R.; Monte, E.; Criado, J. J. J. Inorg. Biochem. 2005, 99, 1558.

    Article  Google Scholar 

  37. Reviews on amine cyclomethylation reactions: (а) Akhmetova, V. R.; Nadyrgulova, G. R.; Niatshina, Z. T.; Dzhemilev, U. M. Chem. Heterocycl. Compd. 2009, 45, 1155. [Khim. Geterotsikl. Soedin. 2009, 1443.] (b) Akhmetova, V. R.; Rakhimova, E. B.; Galimzyanova, N. F.; Ibragimov, A. G. In Bioactive Heterocycles: Synthesis and Biological Evaluation, Ameta, K. L.; Pawar, R. P.; Domb, A. J.,Eds.; Nova Science Publishers: New York, 2012, chap. 5, p. 97.

  38. Review on the chemistry of triazolothiadiazines: Abdel-Wahab, B. F.; Althagafi, I. Phosphorus, Sulfur Silicon Relat. Elem. 2014, 189, 1433.

  39. (а) Angiolini, L.; Jones, R. A. Y.; Katritzky, A. R. Tetrahedron Lett. 1971, 2209. (b) Angiolini, L.; Duke, R. P.; Jones, R. A. Y.; Katritzky, A. R. J. Chem. Soc., Perkin Trans. 2 1972, 674.

  40. Bushmarinov, I. S. Abstr. Diss. Cand. Chem. Sci, Moscow, 2010.

  41. (a) Akhmetova, V. R.; Niatshina, Z. T.; Khabibullina, G. R.; Bushmarinov, I. S.; Borisova, A. O.; Starikova, Z. A.; Korzhova, L. F.; Kunakova, R. V. Russ. Chem. Bull., Int. Ed. 2010, 59, 1002. [Izv. Akad Nauk, Ser. Khim. 2010, 980.] (b) Akhmetova, V. R.; Nadyrgulova, G. R.; Niatshina, Z. T.; Khairullina, R. R.; Starikova, Z. A.; Borisova, A. O.; Antipin, M. Yu.; Kunakova, R. V.; Dzhemilev, U. M. Heterocycles 2009, 78, 45.

  42. Bushmarinov, I. S.; Fedyanin, I. V.; Lyssenko, K. A.; Lapteva, V. L.; Pisarev, S. A.; Palyulin, V. A.; Zefirov, N. S.; Antipin, M. Yu. J. Phys. Chem. A 2011, 115, 12738.

    Article  CAS  Google Scholar 

  43. Akhmetova, V. R.; Khairullina, R. R.; Bushmarinov, I. S.; Tyumkina, T. V.; Yanybin, V. M. ARKIVOC 2011, (viii), 149.

  44. X-ray data for 1,3,5-thiadiazine-2-thiones: (а) Arfan, M.; Tahir, M. N.; Shah, M. I. A.; Iqbal, M. S. Acta Crystallogr., Sect. E: Struct. Rep. Online 2009, 65, o468. (b) Arfan, M.; Tahir, M. N.; Shah, M. I. A.; Khan, R.; Iqbal, M. S. Acta Crystallogr., Sect. E: Struct. Rep. Online 2009, 65, o902. (c) Perez, R.; Suarez, M.; Ochoa, E.; Rodriguez, H.; Martin, N.; Seoane, C.; Novoa, H.; Blaton, N.; Peeters, O. M.; De Ranter, C. Tetrahedron 2001, 57, 7361.

  45. (a) Molero, D.; Coro, J.; Perez, R.; Suarez, M.; Martinez-Alvarez, R.; Herrera, A.; Martin, N. Magn. Reson. Chem. 2007, 45, 93. (b) Molero, D.; Perez, R.; Martinez, R.; Suarez, M.; Rodriguez, H.; Martin, N.; Seoane, C. Magn. Reson. Chem. 2001, 39, 222.

  46. Martinez-Alvarez, R.; Martin, N.; Seoane, C.; Suarez, M.; Perez, R.; Rodriguez, H.; Kayali, N. Rapid Commun Mass Spectrom. 2001, 15, 758.

    Article  CAS  Google Scholar 

  47. Coro, J.; Alvarez-Puebla, R.; Montero, A. L.; Suárez, M.; Martin, N.; Perez-Pineiro, R. J. Mol. Model. 2008, 14, 641.

    Article  CAS  Google Scholar 

  48. Frolov, K. A.; Dotsenko, V. V.; Krivokolysko, S. G. Chem. Heterocycl. Compd. 2012, 48, 1555. [Khim. Geterotsikl. Soedin. 2012, 1668.]

  49. Dotsenko, V. V.; Krivokolysko, S. G.; Rusanov, E. B.; Litvinov, V. P. Russ. Chem. Bull., Int. Ed. 2007, 56, 1437. [Izv. Akad Nauk, Ser. Khim. 2007, 1384.]

  50. (a) Khudina, O. G.; Ivanova, A. E.; Burgart, Ya. V.; Slepukhin, P. A.; Saloutin, V. I.; Chupakhin, O. N.; Kravchenko, M. A. Russ. Chem. Bull., Int. Ed. 2013, 62, 1060. [Izv. Akad Nauk, Ser. Khim. 2013, 1059]. (b) Khudina, O. G.; Ivanova, A. E.; Burgart, Ya. V.; Saloutin, V. I.; Kravchenko, M. A. J. Fluor. Chem. 2013, 147, 31.

  51. El-Sherief, H. A. H.; Hozien, Z. A.; El-Mahdy, A. F. M.; Sarhan, A. A. O. J. Heterocycl. Chem. 2010, 47, 1294.

    Article  CAS  Google Scholar 

  52. Dotsenko, V. V.; Frolov, K. A.; Krivokolysko, S. G.; Chernega, A. N.; Litvinov, V. P. Monatsh. Chem. 2006, 137, 1089.

    Article  CAS  Google Scholar 

  53. Dotsenko, V. V.; Krivokolysko, S. G.; Chernega, A. N.; Litvinov, V. P. Dokl. Chem. 2003, 389(4–6), 92. [Dokl. Akad. Nauk 2003, 389(6), 763.]

  54. Recent review on amine thiomethylation: Akhmetova, V. R.; Rakhimova, E. B. Russ. J. Org. Chem. 2014, 50, 1711. [Zh. Org. Khim. 2014, 50, 1727.]

  55. 55 Niatshina, Z. T. Abstr. Diss. Cand. Chem. Sci., Ufa, 2010.

  56. Wohl, A. Ber. Dtsch. Chem. Ges. 1886, 19, 2344.

    Article  Google Scholar 

  57. Akhmetova, V. R.; Khabibullina, G. R.; Rakhimova, E. B.; Vagapov, R. A.; Khairullina, R. R.; Niatshina, Z. T.; Murzakova, N. N. Mol. Diversity 2010, 14, 463.

    Article  CAS  Google Scholar 

  58. (а) Braithwaite, E. R.; Graymore, J. J. Chem. Soc. 1950, 208. (b) Braithwaite, E. R.; Graymore, J. J. Chem. Soc. 1953, 143.

  59. Flores-Parra, А.; Sánchez-Ruíz, S. A. Heterocycles 1999, 51, 2079.

    Article  CAS  Google Scholar 

  60. Aniline thiomethylation: (а) Khafizova, S. R.; Akhmetova, V. R.; Kunakova, R. V.; Dzhemilev, U. M. Russ. Chem. Bull., Int. Ed. 2003, 52, 1817. [Izv. Akad Nauk, Ser. Khim. 2003, 1722.] (b) Dzhemilev, U. M.; Akhmetova, V. R.; Niatshina, Z. T.; Ibragimov, A. G.; Kunakova, P. V. RF Patent 2440347; Byul. Izobret. 2012, (2). (с) Akhmetova, V. R.; Niatshina, Z. T.; Burakaeva, A. D.; Galimzyanova, N. F.; Kunakova, R. V. Russ. J. Appl. Chem. 2011, 84, 416. [Zh. Prikl. Khim. 2011, 84, 424.]

  61. Takikawa, Y.; Koyama, Y.; Yoshida, T.; Makino, K.; Shibuya, H.; Sato, K.; Otsuka, T.; Shibata, Y.; Onuma, Y.; Aoyagi, S.; Shimada, K.; Kabuto, C. Bull. Chem. Soc. Jpn. 2006, 79, 1913.

    Article  CAS  Google Scholar 

  62. Akhmetova, V. R.; Nadyrgulova, G. R.; Tyumkina, T. V.; Starikova, Z. A.; Antipin, M. Yu.; Kunakova, R. V.; Dzhemilev, U. M. Russ. J. Org. Chem. 2007, 43, 918. [Zh. Org. Khim. 2007, 43, 919.]

  63. Nadyrgulova, G. R. Diss. Cand. Chem. Sci, Ufa, 2006.

  64. Akhmetova, V. R.; Nadyrgulova, G. R.; Khafizova, S. R.; Tyumkina, T. V.; Yakovenko, A. A.; Antipin, M. Yu.; Khalilov, L. M.; Kunakova, R. V.; Dzhemilev, U. M. Russ. Chem. Bull., Int. Ed. 2006, 55, 312. [Izv. Akad. Nauk, Ser. Khim. 2006, 305.]

  65. Akhmetova, V. R.; Niatshina, Z. T.; Starikova, Z. A.; Korzhova, L. F.; Ibragimov, A. G. Russ. J. Org. Chem. 2011, 47, 920. [Zh. Org. Khim. 2011, 47, 903.]

  66. (a) Delépine, M. Ann. Chim. Phys. 1898, 7(15), p. 571. (b) Delépine, M. Bull. Soc. Chim. Paris 1898, Ser. 3, 19, 435.

  67. Le Fevre, C. G.; Le Fevre, R. J. W. J. Chem. Soc. 1932, 1142.

  68. (a) Potekhin, K. A.; Kurkutova, E. N. Sov. Phys. Dokl. 1977, 22, 420. (b) Gleiter, R.; Zefirov, N. S.; Palyulin, V. A.; Potekhin, K. A.; Kurkutova, E. I.; Struchkov, Yu. T.; Antipin, M. Yu. J. Org. Chem. USSR 1978, 14, 1630 [Zh. Org. Khim. 1978, 14, 1630.]

  69. Cadenas-Pliego, G.; Contreras, R.; Flores-Parra, A.; Daran, J. C.; Halut, S. Phosphorus, Sulfur Silicon Relat. Elem. 1993, 84(1–4), 9.

    Article  CAS  Google Scholar 

  70. Akhmetova, V. R.; Safiullina, I. I.; Galimzyanova, N. F.; Khabibullina, G. R.; Mukhamed'yarova, R. R.; Kunakova, R. V.; Starikova, Z. A. RF Patent 2489438; Byul. Izobret. 2013, (22).

  71. Akhmetova, V. R.; Nadyrgulova, G. R.; Tyumkina, T. V.; Starikova, Z. A.; Golovanov, D. G.; Antipin, M. Yu.; Kunakova, R. V.; Dzhemilev, U. M. Russ. Chem. Bull., Int. Ed. 2006, 55, 1824. [Izv. Akad. Nauk, Ser. Khim. 2006, 1758.]

  72. (a) Akhmetova, V. R.; Murzakova, N. N.; Khabibullina, G. R.; Tyumkina, T. V.; Starikova, Z. A.; Bushmarinov, I. S.; Korzhova, L. F. Russ. Chem. Bull., Int. Ed. 2012, 61, 141. [Izv. Akad. Nauk, Ser. Khim. 2012, 139.] (b) Akhmetova, V. R.; Makhmudiyarova, N. N.; Bushmarinov, I. S.; Khabibullina, G. R.; Galimzyanova, N. F. Chem. Heterocycl. Compd. 2013, 49, 1224. [Khim. Geterotsikl. Soedin. 2013, 1311.]

  73. Akhmetova, V. R.; Nadyrgulova, G. R.; Khafizova, S. R.; Khairullina, R. R.; Paramonov, E. A.; Kunakova, R. V.; Dzhemilev, U. M. Russ. J. Org. Chem. 2006, 42, 145. [Zh. Org. Khim. 2006, 42, 151.]

  74. Khafizova, S. R.; Akhmetova, V. R.; Tyumkina, T. V.; Khalilov, L. M.; Kunakova, R. V.; Dzhemilev, U. M. Russ. Chem. Bull., Int. Ed. 2004, 53, 1717. [Izv. Akad. Nauk, Ser. Khim. 2004, 1652].

  75. Murzakova, N. N.; Rakhimova, E. B.; Vasil'yeva, I. V.; Prokof'yev, K. I.; Ibragimov, A. G.; Dzhemilev, U. M. Tetrahedron Lett. 2011, 52, 4090.

    Article  CAS  Google Scholar 

  76. Akhmetova, V. R.; Khairullina, R. R.; Tyumkina, T. V.; Nelyubina, Yu. V.; Smol'yakov, A. F.; Bushmarinov, I. S.; Starikova, Z. A.; Abdullin, M. F.; Kunakova, R. V. Russ. Chem. Bull., Int. Ed. 2010, 59, 425. [Izv. Akad. Nauk, Ser. Khim. 2010, 416].

  77. Khairullina, R. R.; Akmanov, B. F.; Kunakova, R. V.; Ibragimov, A. G.; Dzhemilev, U. M. Russ. Chem. Bull., Int. Ed. 2013, 62, 98. [Izv. Akad. Nauk, Ser. Khim. 2013, 98.]

  78. Akhmetova, V. R.; Khairullina, R. R.; Nadyrgulova, G. R.; Kunakova, R. V.; Dzhemilev, U. M. Russ. J. Org. Chem. 2008, 44, 190. [Zh. Org. Khim. 2008, 44, 200.]

  79. (a) Akhmetova, V. R.; Vagapov, R. A.; Nadyrgulova, G. R.; Tyumkina, T. V.; Starikova, Z. A.; Antipin, M. Yu.; Kunakova, R. V.; Dzhemilev, U. M. Tetrahedron 2007, 63, 11702. (b) Akhmetova, V. R.; Vagapov, R. A.; Nadyrgulova, G. R.; Kunakova, R. V.; Dzhemilev, U. M. Russ. J. Org. Chem. 2007, 43, 940. [Zh. Org. Khim. 2007, 43, 940.]

  80. Reaction of ethylenediamines with aliphatic aldehydes and H2S: (a) Akhmetova, V. R.; Rakhimova, E. B.; Vagapov, R. A.; Minnebaev, A. B.; Kopylova, E. V.; Buslaeva, T. M.; Kunakova, R. V. Trends Heterocycl. Chem. 2011, 15, 33. (b) Akhmetova, V. R.; Vagapov, R. A.; Tyumkina, T. V.; Khabibullina, G. R.; Starikova, Z. A.; Lobov, A. H.; Nelyubina, Yu. V.; Kunakova, R. V.; Dzhemilev, U. M. J. Heterocycl. Chem. 2015, DOI: 10.1002/jhet.2095

  81. Khafizova, S. R.; Akhmetova, V. R.; Korzhova, L. F.; Tyumkina, T. V.; Nadyrgulova, G. R.; Kunakova, R. V.; Kruglov, E. A.; Dzhemilev, U. M. Russ. Chem. Bull., Int. Ed. 2005, 54, 432. [Izv. Akad. Nauk, Ser. Khim. 2005, 423.]

  82. Akhmetova, V. R.; Rakhimova, E. B.; Minnebaev, A. B.; Kunakova, R. V.; Galimzyanova, N. F. Russ. J. Org. Chem. 2012, 48, 202. [Zh. Org. Khim. 2012, 48, 214.]

  83. Akhmetova, V. R.; Rakhimova, E. B.; Vagapov, R. A.; Kunakova, R. V.; Dzhemilev, U. M. Russ. J. Org. Chem. 2008, 44, 499. [Zh. Org. Khim. 2008, 44, 504.]

  84. Dzhemilev, U. M.; Akhmetova, V. R.; Khairullina, R. R.; Ibragomov, A. G.; Kunakova, R. V. RF Patent 2447067; Byul. Izobret. 2012, (10).

  85. Seidel, M. C.; Boettner, F. E. J. Heterocycl. Chem. 1972, 9, 231.

    Article  CAS  Google Scholar 

  86. Redtenbacher, J.; Liebig, J. Liebigs Ann. Chem. 1848, 65, 43.

    Article  Google Scholar 

  87. Ainley, A. D.; Davies, W. H.; Gudgeon, H.; Harland, J. C.; Sexton, W. A. J. Chem. Soc. 1944, 147.

  88. Aboul-Fadl, T.; Hussein, M. A.; El-Shorbagi, A.-N.; Khallil, A.-R. Arch. Pharm. Pharm. Med. Chem. 2002, 335, 438.

    Article  CAS  Google Scholar 

  89. Radwan, A. A.; Al-Dhfyan, A.; Abdel-Hamid, M. K.; Al-Badr, A. A.; Aboul-Fadl, T. Arch. Pharm. Res. 2012, 35, 35.

    Article  CAS  Google Scholar 

  90. Radwan, A. A.; Hussein, N. A. Bull. Pharm. Sci., Assiut Univ. 2005, 28, pt. 2, 255.

  91. Sağlam, E.; Saraç, S.; Kiliç, E.; Özalp, M.; Ertan, M. Turk. J. Pharm. Sci. 2011, 8(2), 159.

    Google Scholar 

  92. Coro, J.; Little, S.; Yardley, V.; Surez, M.; Rodriguez, H.; Martin, N.; Perez-Pineiro, R. Arch. Pharm. Chem. Life Sci. 2008, 341, 708.

    Article  CAS  Google Scholar 

  93. Pérez, R.; Reyes, O.; Suárez, M.; Garay, H. E.; Cruz, L. J.; Rodríguez, H.; Molero-Vichez, M. D.; Ochoa, C. Tetrahedron Lett. 2000, 41, 613.

    Article  Google Scholar 

  94. Rodríguez, H.; Coro, J.; Suárez, M.; Martínez-Álvarez, R.; Martín, N.; Albericio, F. ARKIVOC 2012, viii, 326.

  95. Ji, X.; Zhong, Z.; Chen, X.; Xing, R.; Liu, S.; Wang, L.; Li, P. Bioorg. Med. Chem. Lett. 2007, 17, 4275.

    Article  CAS  Google Scholar 

  96. Sert, S.; Ercag, A.; Sentürk, O. S.; Sterenberg, B. T.; Udachin, K. A.; Özdemir, Ü.; Sarikahya, F. U. Polyhedron 2003, 22, 1689.

    Article  CAS  Google Scholar 

  97. Recent studies on the synthesis of perhydro-1,3,5-triаzine-2-thiones by aminomethylation of thioureas: (а) Lazarev, D. B.; Ramsh, S. M.; Ivanenko, A. G. Russ. J. Gen. Chem. 2000, 70, 442. [Zh. Obshch. Khim. 2000, 70, 475]. (b) Dandia, A.; Arya, K; Sati, M. Synth. Commun. 2004, 34, 1141. (c) Rajanarendar, E.; Ramu, K.; Karunakar, D.; Ramesh. P. J. Heterocycl. Chem. 2005, 42, 711. (d) Garibov, E. N.; Rzaeva, I. A.; Shykhaliev, N. G.; Kuliev, A. I.; Farzaliev, V. M.; Allakhverdiev, M. A. Russ. J. Appl. Chem. 2010, 83, 707. [Zh. Prikl. Khim. 2010, 83, 655.] (e) Minyan, S.; Ramsh, S. M.; Fundamensky, V. S.; Solov'eva, S. Yu.; Zakharov, V. I. Russ. J. Gen. Chem. 2012, 82, 236. [Zh. Obshch. Khim. 2012, 82, 240.]

  98. Sazonov, A. A. Abstr. Diss. Cand. Chem. Sci., Saratov, 2005.

  99. Klochkova, I. N.; Sazonov, A. A. Izv. Vuzov. Khimiya and Khim. Tekhnologiya 2005, 48(3), 106.

    CAS  Google Scholar 

  100. Zhang, Z.; Wang, S.; Zhang, G. J. Heterocycl. Chem. 2012, 49, 433.

    Article  CAS  Google Scholar 

  101. Musorin, G. K. Russ. J. Gen. Chem. 2003, 73, 323. [Zh. Obshch. Khim. 2003, 73, 347.]

  102. Furin, G. G.; Zhuzhgov, E. L. Russ. J. Gen. Chem. 2004, 74, 1534. [Zh. Obshch. Khim. 2004, 74, 1655.]

  103. Aly, A. A.; El-Shaieb, K. M. J. Chem. Res. 2007, 207.

  104. Katritzky, A. R.; Vakulenko, A. V.; Xu, Y.-J.; Steel, P. J. J. Org. Chem. 2002, 67, 4960.

    Article  CAS  Google Scholar 

  105. Shimada, K.; Aikawa, K.; Fujita, T.; Sato, M.; Goto, K.; Aoyagi, S.; Takikawa, Y.; Kabuto, C. Bull. Chem. Soc. Jpn. 2001, 74, 511.

    Article  CAS  Google Scholar 

  106. See, for example: (a) Giordano, C.; Belli, A. Synthesis 1975, 789. (b) Giordano, C.; Belli, A.; Erbea, R.; Panossian, S. Synthesis 1979, 801.

  107. Giordano, C.; Belli, A.; Abis, L. Tetrahedron Lett. 1979, 17, 1537.

    Article  Google Scholar 

  108. Wijma, J.; van Daalen, J. J.; Daams, J.; van Deursen, F. W. J. Agric. Food Chem. 1970, 18, 674.

    Article  CAS  Google Scholar 

  109. Drach, B. S.; Brovarets, V. S.; Smolii, O. B. Syntheses of Nitrogen-containing Heterocyclic Compounds on the Basis of Amidoalkylating Agents [in Russian]; Kuhar', V. P., Ed.; Naukova Dumka: Kiev, 1992.

  110. Brovarets, V.; Zyabrev, V. Synthesis of Nitrogen Heterocycles on the Basis of α-Haloalkylamides [in Russian]; LAP LAMBERT Academic Publishing, 2012.

  111. Wang, Z. Y.; You, T. P.; Shi, H. J.; Shi, H. X. Molecules 1996, 1(8), 89.

    Article  CAS  Google Scholar 

  112. Hozien, Z. A.; Sarhan, A. A. O.; El-Sherief, H. A. H.; Mahmoud, A. M. Z. Naturforsch. 1997, 52b, 1401.

    Google Scholar 

  113. Synthesis of sym-triazolo[3,4-b][1,3,5]thiadiazines: (a) Shi, H. J.; Wang, Z. Y.; Shi, H. X. Chimia 1997, 51, 529; Ref. Zh. Khim. 1998, 13Zh272. (b) Wang, Z. Y.; You, T. P.; Shi, H. J.; Shi, H. X. Gaodeng Xuexiao Huaxue Xuebao (Chem. J. Chin. Univ.) 1997, 18, 550 [in Chinese]; Chem. Abstr. 1997, 127, 95265t. (c) Shi, H. X.; Shi, H. J.; Wang, Z. Y. Youji Huaxue (Chin. J. Org. Chem.) 2000, 20, 344 [in Chinese]; Chem. Abstr. 2000, 133, 120280c. (d) Wang, Z. Y.; Shi, H. X.; Shi, H. J. Synth. Commun. 2001, 31, 2841.(e) Shi, H.; Wang, Z.; Shi, H. Synth. Commun. 1999, 29, 2027. (f) Sarfraz, T. B.; Husain, S. A.; Murtaza, N.; Siddiqui, B. S. Pak. J. Sci. Ind. Res. 2000, 43, 334. (g) Shi, H. J.; Shi, H. X.; Wang, Z. J. Heterocycl. Chem. 2001, 38, 929.

  114. Mahmoud, A. M.; El-Sherif, H. A. H.; Habib, O. M. A.; Sarhan, A. A. O. Phosphorus, Sulfur Silicon Relat. Elem. 2007, 182, 1757.

    Article  CAS  Google Scholar 

  115. Hozien, Z. A. J. Chem. Res. (S) 2000, (3), 99.

  116. Frolov, K. A.; Dotsenko, V. V.; Krivokolysko, S. G.; Litvinov, V. P. Russ. Chem. Bull., Int. Ed. 2005, 54, 2226. [Izv. Akad. Nauk, Ser. Khim. 2005, 2158].

  117. Sarhan, A. E.-W. A. O.; Abdel-Hafez, S. H.; El-Sherief, H.; Aboel-Fadl, T. Synth. Commun. 2006, 36, 987.

    Article  CAS  Google Scholar 

  118. Yadav, L. D. S.; Vaish, A.; Sharma, S. J. Agric. Food Chem. 1994, 42, 811.

    Article  CAS  Google Scholar 

  119. Dotsenko, V. V.; Krivokolysko, S. G.; Litvinov, V. P. Monatsh. Chem. 2008, 139, 271.

    Article  CAS  Google Scholar 

  120. Dotsenko, V. V.; Krivokolysko, S. G.; Litvinov, V. P. Monatsh. Chem. 2008, 139, 657.

    Article  CAS  Google Scholar 

  121. Dotsenko, V. V.; Krivokolysko, S. G.; Litvinov, V. P. Chem. Heterocycl. Compd. 2007, 43, 517. [Khim. Geterotsikl. Soedin. 2007, 621.]

  122. Dotsenko, V. V.; Suikov, S. Yu.; Pekhtereva, T. M.; Krivokolysko, S. G. Chem. Heterocycl. Compd. 2013, 49, 1009. [Khim. Geterotsikl. Soedin. 2013, 1082.]

  123. Dotsenko, V. V.; Krivokolysko, S. G.; Rusanov, E. B.; Gutov, A. V.; Litvinov, V. P. Chem. Heterocycl. Compd. 2007, 43, 906. [Khim. Geterotsikl. Soedin. 2007, 1075.]

  124. Dotsenko, V. V.; Krivokolysko, S. G.; Litvinov, V. P. Russ. Chem. Bull., Int. Ed. 2005, 54, 2692. [Izv. Akad. Nauk, Ser. Khim. 2005, 2605.]

  125. Dotsenko, V. V.; Krivokolysko, S. G.; Chernega, A. N.; Litvinov, V. P. Monatsh. Chem. 2007, 138, 35.

    Article  CAS  Google Scholar 

  126. Dotsenko, V. V.; Krivokolysko, S. G.; Litvinov, V. P. Russ. Chem. Bull., Int. Ed. 2012, 61, 136. [Izv. Akad. Nauk, Ser. Khim. 2012, 134.]

  127. Dotsenko, V. V.; Krivokolysko, S. G.; Litvinov, V. P.; Rusanov, E. B. Dokl. Chem. 2007, 413, pt. 1, 68. [Dokl. Akad. Nauk 2007, 413(3), 345.]

  128. Dotsenko, V. V.; Krivokolysko, S. G.; Chernega, A. N.; Litvinov, V. P. Russ. Chem. Bull., Int. Ed. 2007, 56, 1053. [Izv. Akad. Nauk, Ser. Khim. 2007, 1014.]

  129. Dotsenko, V. V.; Krivokolysko, S. G.; Litvinov, V. P. Chem. Heterocycl. Compd. 2007, 43, 1455. [Khim. Geterotsikl. Soedin. 2007, 1709.]

  130. Frolov, K. A.; Dotsenko, V. V.; Krivokolysko, S. G.; Litvinov, V. P. Chem. Heterocycl. Compd. 2012, 48, 1117. [Khim. Geterotsikl. Soedin. 2012, 1197.]

  131. Dotsenko, V. V.; Frolov, K. A.; Pekhtereva, T. M.; Papaianina, O. S.; Suykov, S. Yu.; Krivokolysko, S. G. ACS Comb. Sci. 2014, 16, 543.

    Article  CAS  Google Scholar 

  132. Vidović, D.; Busby, S. A.; Griffin, P. R.; Schürer, S. C. ChemMedChem 2011, 6, 94.

    Article  Google Scholar 

  133. Dotsenko, V. V.; Krivokolysko, S. G.; Litvinov, V. P. Russ. Chem. Bull., Int. Ed. 2012, 61, 131. [Izv. Akad. Nauk, Ser. Khim. 2012, 129.]

  134. Dotsenko, V. V.; Krivokolysko, S. G. Chem. Heterocycl. Compd. 2012, 48, 672. [Khim. Geterotsikl. Soedin. 2012, 721.]

  135. Dotsenko, V. V.; Krivokolysko, S. G.; Litvinov, V. P. Monatsh. Chem. 2007, 138, 489.

    Article  CAS  Google Scholar 

  136. Dotsenko, V. V.; Krivokolysko, S. G.; Litvinov, V. P. Russ. Chem. Bull., Int. Ed. 2007, 56, 2482. [Izv. Akad. Nauk, Ser. Khim. 2007, 2397].

  137. Dotsenko, V. V.; Krivokolysko, S. G.; Litvinov, V. P. Chem. Heterocycl. Compd. 2005, 41, 1428. [Khim. Geterotsikl. Soedin. 2005, 1695.]

  138. Dyachenko, V. D.; Nikishin, A. A.; Dyachenko, A. D. Russ. J. Org. Chem. 2012, 48, 1135. [Zh. Org. Khim. 2012, 48, 1135.]

  139. Dotsenko, V. V.; Frolov, K. A.; Krivokolysko, S. G.; Litvinov, V. P. Russ. Chem. Bull., Int. Ed. 2009, 58, 1479. [Izv. Akad. Nauk, Ser. Khim. 2009, 1436.]

  140. Dotsenko, V. V.; Krivokolysko, S. G.; Litvinov, V. P. Russ. Chem. Bull., Int. Ed. 2007, 56, 1474. [Izv. Akad. Nauk, Ser. Khim. 2007, 1420].

  141. Dotsenko, V. V.; Frolov, K. A.; Krivokolysko, S. G. Chem. Heterocycl. Compd. 2012, 48, 642. [Khim. Geterotsikl. Soedin. 2012, 689.]

  142. Pospieszny, T.; Wyrzykiewicz, E. Tetrahedron Lett. 2008, 49, 5319.

    Article  CAS  Google Scholar 

  143. Aminomethylation of 6-methyl-2-thiouracil: (a) Monti, L.; Franchi, G. Gazz. Chim. Ital. 1955, 85, 516. (b) Besyadetskaya, E. I.; Zubenko, V. G.; Lozyuk, L. V.; Pharm. Chem. J. 1980, 14, 451. [Khim.-Farm. Zh. 1980, 14(7), 42.] (с) Pospieszny, T.; Małecka, I.; Paryzek, Z. Tetrahedron Lett. 2010, 51, 4166.

  144. Recent examples of aminomethylation of 6-amino-2-thiouracil: (а) Mohamed, M. S.; Awad, S. M.; Sayed, A. I. Molecules 2010, 15, 1882. (b) Garcia, D.; Jatczak, M.; Muylaert, K.; De Coen, L. M.; Stevens, C. V. Eur. J. Org. Chem. 2013, 1732.

  145. Khudina, O. G.; Ivanova, A. E.; Burgart, Ya. V.; Saloutin, V. I. Chem. Heterocycl. Compd. 2014, 50, 901. [Khim. Geterotsikl. Soedin. 2014, 976.]

  146. Vlasova, L. I.; Baibulatova, N. Z.; Dokichev, V. A.; Tomilov, Yu. V. Russ. Chem. Bull., Int. Ed. 2012, 61, 2129. [Izv. Akad. Nauk, Ser. Khim. 2012, 2112.]

  147. Vlasova, L. I.; Baibulatova, N. Z.; Latypova, D. R.; Yunusov, M. S.; Dokichev, V. A.; Tomilov, Yu. V. Russ. Chem. Bull., Int. Ed. 2005, 54, 479. [Izv. Akad. Nauk, Ser. Khim. 2005, 469.]

  148. Eltsov, O. S.; Kamalova, E. A.; Mokrushin, V. S. Mendeleev Commun. 2006, 16, 32.

    Article  Google Scholar 

  149. Eltsov, O. S.; Smirnova, M. V.; Morzherin, Yu. Yu.; Belskaiya, N. P.; Mokrushin, V. S. ARKIVOC 2008, (xvii), 306.

  150. Vovk, M. V.; Dorokhov, V. I.; Samarai, L. I. Chem. Heterocycl. Compd. 2004, 40, 241. [Khim.Geterotsikl. Soedin. 2004, 282.]

  151. Furin, G. G.; Zhuzhgov, E. L. Russ. J. Org. Chem. 2005, 41, 434. [Zh. Org. Khim. 2005, 41, 441.]

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Victor V. Dotsenko.

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2015, 51(2), 109–127

Here and further the corresponding author is marked with *.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Dotsenko, V.V., Frolov, K.A. & Krivokolysko, S.G. Synthesis of partially hydrogenated 1,3,5-thiadiazines by Mannich reaction. Chem Heterocycl Comp 51, 109–127 (2015). https://doi.org/10.1007/s10593-015-1668-7

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-015-1668-7

Keywords

Navigation