Abstract
Simple and efficient synthesis of novel 5-phenyl-5,5a-dihydro-4bH-spiro[diindeno[1,2-b:2′,1′-e]pyridine-11,11′-indeno[2,1-b]quinoxaline]-10,12(10aH,11aH)-diones via a one-pot pseudo five-component cyclocondensation reaction of 1H-indene-1,2,3-trione, benzene-1,2-diamine, 1H-indene-1,3(2H)-dione, and anilines in refluxing acetonitrile is reported.
Graphical abstract
Similar content being viewed by others
References
Nair V, Rajesh C, Vinod AU, Bindu S, Sreekanth AR, Mathen JS, Balagopal L (2003) Acc Chem Res 36:899
Armstrong RW, Combs AP, Tempest PA, Brown SD, Keating TA (1996) Acc Chem Res 29:123
Tietze LF, Modi A (2000) Med Res Rev 20:304
Domling A, Ugi I (2000) Angew Chem Int Ed 39:3168
Weber L (2002) Curr Med Chem 9:2085
Jiang B, Rajale T, Wever W, Tu SJ, Li G (2010) Chem Asian J 5:2318
Ruijter E, Scheffelaar R, Orru RV (2011) Angew Chem Int Ed 50:6234
Pokhodylo NT, Matiychuk VS, Obushak MD (2009) J Comb Chem 11:481
Zhang L, Lushington GH, Neuenswander B, Hershberger JC, Malinakova HC (2008) J Comb Chem 10:285
Tu SJ, Zhang XH, Han ZG, Cao XD, Wu SS, Yan S, Hao WJ, Zhang G, Ma N (2009) J Comb Chem 11:428
Wang XS, Li Q, Wu JR, Tu SJ (2009) J Comb Chem 11:433
Zhu J, Bienayme H (2005) Multicomponent reactions. Wiley-VCH, Weinheim
Noga EJ, Barthalmus GT, Mitchell MK (1986) Cell Biol Int Rep 10:239
Craig PN (1991) In: Drayton CJ (ed) Comprehensive medicinal chemistry, vol 8. Pergamon, New York
Franklin EC (1935) Chem Rev 16:305
Bergstrom FW (1944) Chem Rev 35:77
Lichtenthaler FW (2002) Acc Chem Res 35:728
Padwa A, Waterson AG (2000) Curr Org Chem 4:175
Orru RVA, De Greef M (2003) Synthesis 1471
Kirsch G, Hesse S, Comel A (2004) Curr Org Chem 1:47
Kotharkar SA, Shinde DB (2006) Bioorg Med Chem Lett 16:6181
El-Hawash SA, Habib NS, Kassem MA (2006) Arch Pharm (Weinheim) 339:564
Khan SA, Saleem K, Khan Z (2007) Eur J Med Chem 42:103
Corona P, Vitale G, Loriga M, Paglietti G, La Colla P, Collu G, Sanna G, Loddo R (2006) Eur J Med Chem 41:1102
Tandon VK, Yadav DB, Maurya HK, Chaturvedi AK, Shukla PK (2006) Bioorg Med Chem 14:6120
Abid M, Azam A (2006) Bioorg Med Chem Lett 16:2812
Zarranz B, Aldana I, Jaso A, Monge A (2004) Bioorg Med Chem 12:3711
Yan L, Liu FW, Dai GF, Liu HM (2007) Bioorg Med Chem Lett 17:609
Grande F, Aiello F, Grazia OD, Brizzi A, Garofalo A, Neamati N (2007) Bioorg Med Chem 15:288
Lenzi O, Colotta V, Catarzi D, Varano F, Filacchioni G, Martini C, Trincavelli L, Ciampi O, Varani K, Marighetti F, Morizzo E, Moro S (2006) J Med Chem 49:3916
Jung JK, Jung EK, Nam-Goong K, Cho JS, Kim HM, Park SG, Yoo YA, Kwon JH, Lee HS (2006) Arch Pharm Res 9:276
Carta A, Loriga M, Piras S, Paglietti G, La Colla P, Busonera B, Collu G, Loddo R (2006) Med Chem 2:113
Liu CH, Wang B, Li WZ, Yun LH, Liu Y, Su RB, Li J, Liu H (2004) Bioorg Med Chem 12:4701
Colotta V, Catarzi D, Varano F, Calabri FR, Lenzi O, Filacchioni G, Martini C, Trincavelli L, Deflorian FM (2004) J Med Chem 47:3580
Zarranz B, Jaso A, Lima LM, Aldana I, Monge A, Maurel S, Sauvain M (2006) Braz J Pharm Sci 42:357
Zarranz B, Jaso A, Aldana I, Monge A, Maurel S, Deharo E, Jullian V, Sauvain M (2005) Arzneim Forsch 55:754
Guillon J, Grellier P, Labaied M, Sonnet P, Leger JM, Deprez-Poulain R, Forfar-Bares I, Dallemagne P, Lemaitre N, Pehourcq F, Rochette J, Sergheraert C, Jarry C (2004) J Med Chem 47:1997
Zarranz B, Aldana I, Jaso A, Monge A (2003) Bioorg Med Chem 11:2149
Lieu F, Ouellet C, Ruediger EH, Belema M, Qiu Y, Yang X, Banville J, Burke JR, Gregor KR, MacMaster JF, Martel A, McIntyre KW, Pattoli MA, Zusi FC, Vyas D (2007) Bioorg Med Chem Lett 17:1233
Singh SK, Saibaba V, Ravikumar V, Rudrawar SV, Daga P, Rao CS, Akhila V, Hegde P, Rao YK (2004) Bioorg Med Chem 12:1881
Vierfond JM, Legendre L, Martin C, Rinjard P, Miocque M (1990) Eur J Med Chem 25:251
Carta A, Piras S, Loriga G, Paglietti G (2006) Mini Rev Med Chem 6:1179
Ortega MA, Aldana I, Jaso A, Monge A, Montoya ME, Sainz Y, Zarranz B (2002) Arzneim Forsch 52:113
Aldana OA, Monge I, Zarranz A (2003) Eur J Med Chem 38:791
Zanetti LA, Sechi P, Molicotti S, Cannas A, Bua A, Deriu A, Paglietti G (2005) Int J Antimicrob Agents 25:179
Sun G, Uretsky NJ, Wallace LJ, Shams G, Weinstein DM, Miller DD (1996) J Med Chem 39:4430
Fisher MH, Lusi A, Egerton JR (1977) J Pharm Sci 66:1349
Bahekar RH, Jain MR, Gupta AA, Goel A, Jadav PA, Patel DN, Prajapati VM, Patel PR (2007) Arch Pharm 340:359
Dell A, William DH, Morris HR, Smith GA, Feeney J, Roberts GCK (1975) J Am Chem Soc 97:2497
Heravi MM, Bakhtiari K, Tehrani MH, Javadi NM, Oskooie HA (2006) Arkivoc xvi:16
Raw SA, Wilfred CD, Taylor RJK (2003) Chem Commun 18:2286
Bigge CF, Malone TC, Boxer PA, Nelson CB, Ortwine DF, Schelkun RM, Retz DM, Lescosky LJ, Borosky SA, Vartanian MG (1995) J Med Chem 38:3720
Cheng Ch, Jiang B, Tu SJ, Li G (2011) Green Chem 13:2107
Sehlstedt U, Aich P, Bergman J, Vallberg EI, Norden B, Graslund A (1998) J Mol Biol 278:31
Ghahremanzadeh R, Amanpour T, Bazgir A (2009) J Heterocycl Chem 46:1266
Ghahremanzadeh R, Amanpour T, Bazgir A (2010) J Heterocycl Chem 47:46
Ghahremanzadeh R, Ahadi S, Bazgir A (2009) Tetrahedron Lett 50:7379
Ghahremanzadeh R, Amanpour T, Sayyafi M, Bazgir A (2010) J Heterocycl Chem 47:421
Ghahremanzadeh R, Imani Shakibaei G, Ahadi S, Bazgir A (2010) J Comb Chem 12:191
Ghahremanzadeh R, Ahadi S, Imani Shakibaei G, Bazgir A (2010) Tetrahedron Lett 51:499
Ghahremanzadeh R, Sayyafi M, Ahadi S, Bazgir A (2009) J Comb Chem 11:393
Acknowledgments
We gratefully acknowledge financial support from the Avicenna Research Institute.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Amanpour, T., Bazgir, A., Ardekani, A.M. et al. Pseudo five-component synthesis of 5-phenyldihydrospiro[diindenopyridine-indenoquinoxaline]dione derivatives via a one-pot condensation reaction. Monatsh Chem 145, 627–632 (2014). https://doi.org/10.1007/s00706-013-1118-0
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s00706-013-1118-0