Abstract
A number of 4-dialkylamino-5-mercapto-1,2-dithiole-3-thiones were synthesized by reactions of alkyl(diisopropyl)amines with S2Cl2. Their reactions with S2Cl2—DABCO unexpectedly gave 5-chloro-4-dialkylamino-1,2-dithiol-3-ones.
Similar content being viewed by others
References
C. Th. Pedersen, Adv. Heterocycl. Chem., 1982, 31, 63; C. Th. Pedersen, Sulfur Rep., 1995, 16, 173; D. M. McKinnon, in Comprehensive Heterocyclic Chemistry; Eds A. R. Katritzky and C. W. Rees, Pergamon, Oxford, 1984; Vol. 6, Ch. 4.31; D. M. McKinnon, in Comprehensive Heterocyclic Chemistry II; Eds A. R. Katritzky, C. W. Rees, and E. F. V. Scriven, Elsevier, Oxford, 1996; Vol. 3, Ch. 11.
J. S. Wang, X. Shen, X. He, Y. R. Zhu, B. C. Zhang, J.-B. Wang, G. S. Qian, S. Y. Kuang, A. Zarba, P. A. Egner, L. P. Jacobson, A. Munoz, K. J. Helzlsouer, J. D. Groopman, and T. W. Kensler, J. Nat. Cancer Inst., 1999, 91, 347.
B. Drukarch, E. Schepens, J. C. Stoof, and C. H. Langeveld, Eur. J. Pharmacol., 1997, 329, 259.
P. Misra, S. Misra, R. Mahapatra, and A. Mittra, J. Indian Chem. Soc., 1979, 61, 404.
P. Frere, A. Belyasmine, Y. Gouriou, M. Jubault, A. Gorgues, G. Duguay, S. Wood, C. D. Reynolds, and M. R. Bryce, Bull. Soc. Chim. Fr., 1995, 132, 975; T.-T. Nguyen, Y. Gouriou, M. Salle, P. Frere, M. Jubault, A. Gorgues, L. Toupet, and A. Riou, Bull. Soc. Chim. Fr., 1996, 133, 301.
D. D. Mysyk, I. F. Perepichka, D. F. Perepichka, M. R. Bryce, A. F. Popov, L. M. Goldenberg, and A. J. Moore, J. Org. Chem., 1999, 64, 6937; I. F. Perepichka, D. F. Perepichka, M. R. Bryce, A. J. Moore, and N. I. Sokolov, Synth. Met., 2001, 121, 1487.
C. W. Rees, A. J. P. White, D. J. Williams, O. A. Rakitin, C. F. Marcos, C. Polo, and T. Torroba, J. Org. Chem., 1998, 63, 2189.
L. S. Konstantinova, N. V. Obruchnikova, O. A. Rakitin, C. W. Rees, and T. Torroba, J. Chem. Soc., Perkin Trans. 1, 2000, 3421.
C. W. Rees, A. J. P. White, D. J. Williams, O. A. Rakitin, L. S. Konstantinova, C. F. Marcos, and T. Torroba, J. Org. Chem., 1999, 64, 5010.
S. Barriga, L. S. Konstantinova, C. F. Marcos, O. A. Rakitin, C. W. Rees, T. Torroba, A. J. P. White, and D. J. Williams, J. Chem. Soc., Perkin Trans. 1, 1999, 2237.
L. S. Konstantinova, O. A. Rakitin, and C. W. Rees, Mendeleev Commun., 2001, 165.
S. Barriga, P. Fuertes, C. F. Marcos, and T. Torroba, J. Org. Chem., 2004, 69, 3672.
M. Garsia-Valverde, P. Pascual, and T. Torroba, Org. Lett., 2003, 5, 929.
N. S. Deno and R. E. Fruit, J. Am. Chem. Soc., 1968, 90, 3502.
S. I. Suminov, Vestn. Mosk. Univ., Ser. 2: Khim., 1967, 75 [Moscow Univ. Chem. Bull., 1967, 75 (Engl. Transl.)].
J. H. Burckhalter, E. M. Jones, W. F. Holcomb, and L. A. Sweet, J. Am. Chem. Soc., 1943, 65, 2012.
R. Moore, J. Am. Chem. Soc., 1946, 68, 1657.
Author information
Authors and Affiliations
Additional information
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 1, pp. 143–147, January, 2006.
Rights and permissions
About this article
Cite this article
Konstantinova, L.S., Berezin, A.A., Lysov, K.A. et al. Synthesis of 5-mercapto-1,2-dithiole-3-thiones and their transformation into 5-chloro-1,2-dithiol-3-ones. Russ Chem Bull 55, 147–151 (2006). https://doi.org/10.1007/s11172-006-0228-9
Received:
Revised:
Issue Date:
DOI: https://doi.org/10.1007/s11172-006-0228-9