Cascade synthesis of 1,2-dihydropyridine from dienaminodioate and an imine: A three-component approach

Tetrahedron Letters

Volumn 54, Issue 29, 2013, Pages 3810-3812

  Challa, Chandrasekhar ^a   John, Manju ^a   Lankalapalli, Ravi S ^a  

^a REGIONAL RESEARCH LABORATORY CSIR   (India)

Author keywords

1,2 Dihydropyridine (1,2 DHP); Dienaminodioate; Imine

Indexed keywords

1,2 DIHYDROPYRIDINE; ALDEHYDE; AMINE; ANILINE; DIENAMINODIOATE; IMINE; PYRIDINE DERIVATIVE; SOLVENT; TRIFLUOROACETIC ACID; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; ONE POT SYNTHESIS; ROOM TEMPERATURE;

EID: 84879006579     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2013.05.037     Document Type: Article

References (36)

1. A. Hantzsch Justus Liebigs Ann. Chem. 215 1882 1 82
2. For a recent review on DHPs and references of reviews on DHPs cited therein, see: J.A. Bull, J.J. Mousseau, G. Pelletier, and A.B. Charette Chem. Rev. 112 2012 2642 2713
3. For recent reviews on 1,4-DHP based pharmaceuticals, see: N. Edraki, A.R. Mehdipour, M. Khoshneviszadeh, and R. Miri Drug Discovery Today 14 2009 1058 1066
4. J.-Ping Wan, and Y. Liu RSC Adv. 2 2012 9763 9777
5. C. Safak, and R. Simsek Mini-Rev. Med. Chem. 6 2006 747 755
6. A.B. Charette, M. Grenon, A. Lemire, M. Pourashraf, and J. Martel J. Am. Chem. Soc. 123 2001 11829 11830
7. A. Lemire, M. Grenon, M. Pourashraf, and A.B. Charette Org. Lett. 6 2004 3517 3520
8. F. Palacios, C. Alonso, G. Rubiales, and J.M. Ezpeleta Eur. J. Org. Chem. 2001 2115 2122
9. D.W. Young, and D.L. Comins Org. Lett. 7 2005 5661 5664
10. N. Takenaka, Y. Huang, and V.H. Rawal Tetrahedron 58 2002 8299 8305
11. H. Nakano, K. Osone, M. Takeshita, E. Kwon, C. Seki, N. Matsuyama, and Y. Kohari Chem. Commun. 46 2010 4827 4829
12. G.R. Krow, Q. Huang, S.W. Szczepanski, F.H. Hausheer, and P.J. Caroll J. Org. Chem. 72 2007 3458 3466
13. R.M. Martin, R.G. Bergman, and J.A. Ellman Org. Lett. 15 2013 444 447
14. C. Schroif-Gregoire, N. Travert, A. Zaparucha, and A. Al-Mourabit Org. Lett. 8 2006 2961 2964
15. F. Palacios, E. Herran, and G. Rubiales J. Org. Chem. 64 1999 6239 6246
16. I. Yavari, M.J. Bayat, M. Sirouspour, and S. Souri Tetrahedron 66 2010 7995 7999
17. D. Tejedor, G. Mendez-Abt, and F. García-Tellado Chem. Eur. J. 16 2010 428 431
18. H. Wei, Y. Wang, B. Yue, and P.F. Xu Adv. Synth. Catal. 352 2010 2450 2454
19. J.P. Wan, S.F. Gan, G.L. Sun, and Y.J. Pan J. Org. Chem. 74 2009 2862 2865 and the references cited therein
20. D.L. Comins, H. Hong, and J.M. Salvador J. Org. Chem. 56 1991 7197 7199
21. For recent metal catalyzed synthesis of 1,2-DHPs, see: T. Harschneck, and S.F. Kirsch J. Org. Chem. 76 2011 2145 2156
22. D.A. Colby, R.G. Bergman, and J.A. Ellman J. Am. Chem. Soc. 130 2008 3645 3651
23. M. Motamed, E.M. Bunnelle, S.W. Singaram, and R. Sarpong Org. Lett. 9 2007 2167 2170
24. M.R. Fructos, E. Alvarez, M. Mar Diaz-Requezo, and P.J. Perez J. Am. Chem. Soc. 132 2010 4600 4607
25. L. Maestre, M.R. Fructos, M.M. Díaz-Requejo, and P.J. Pérez Organometallics 31 2012 7839 7843
26. B. Brunner, N. Stoigaitis, and M. Lautens Org. Lett. 8 2006 3473 3476
27. K. Oshima, T. Ohmura, and M. Suginome J. Am. Chem. Soc. 134 2012 3699 3702
28. K. Oshima, T. Ohmura, and M. Suginome J. Am. Chem. Soc. 133 2011 7324 7327
29. E. Ichikawa, M. Suzuki, K. Yabu, M. Albert, M. Kanai, and M. Shibasaki J. Am. Chem. Soc. 126 2004 11808 11809 and the references cited therein
30. For formation of dienaminodiesters, see: W. Bottomley Tetrahedron Lett. 8 1967 1997 1999
31. W. Bottomley, J.N. Phillips, and J.G. Wilson Tetrahedron Lett. 8 1967 2957 2961
32. M.A. Khan, and H. Adams Tetrahedron Lett. 40 1999 5389 5390
33. J. Adams, A. Hardin, and F. Vounatsos J. Org. Chem. 71 2006 9895 9898 and references cited therein
34. T. Sirijindalert, K. Hansuthirakul, P. Rashatasakhon, M. Sukwattanasinitt, and A. Ajavakom Tetrahedron 66 2010 5161 5167
35. P.J. Stevenson, and I. Graham ARKIVOC 2003 139 144
36. N. Anghelide, C. Draghici, and D. Raileanu Tetrahedron 30 1974 623 632