L-Proline catalyzed efficient and convenient synthesis of substituted 2H-chromenes by three-component reaction

Tetrahedron Letters

Volumn 55, Issue 6, 2014, Pages 1127-1131

  Chandrasekhara Rao, L ^a   Meshram, H M ^a   Satish Kumar, N ^a   Nageswara Rao, N ^a   Jagadeesh Babu, N ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

2H Chromens; 4 Dione; l Proline; Pentane 2; Salicylaldehyde

Indexed keywords

EID: 84894918313     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2013.10.091     Document Type: Article

References (48)

1. Zhendong, J.; Ying, K. Total synthesis of daurichromenic acid. PCT Int. Appl. WO 2004058738, 2004.
2. N. Iwata, N. Wang, X. Yao, and S. Kitanaka J. Nat. Prod. 67 2004 1106
3. H. Hu, T.J. Harrison, and P.D. Wilson J. Org. Chem. 69 2004 3782
4. R. Korec, K.H. Sensch, and T. Zoukas Arzneim. Forsch. 50 2000 122
5. F. Cassidy, M.J. Evan, M.S. Hadel, A.H. Halodij, P.E. Leach, and G. Sternp J. Med. Chem. 35 1992 1623
6. K.C. Nicolaou, J.A. Pfefferkorn, A.J. Roecker, G.-Q. Cao, S. Barluenga, and H.J. Mitchell J. Am. Chem. Soc. 122 2000 9939
7. K.C. Nicolaou, J.A. Pfefferkorn, H.J. Mitchell, A.J. Roecker, S. Barluenga, G.-Q. Cao, R.L. Affleck, and J.E. Lillig J. Am. Chem. Soc. 122 2000 9954
8. K.C. Nicolaou, J.A. Pfefferkorn, S. Barluenga, H.J. Mitchell, A.J. Roecker, and G.-Q. Cao J. Am. Chem. Soc. 122 2000 9968
9. Y. Kashiwada, K. Yamazaki, Y. Ikeshiro, T. Yamasisbi, T. Fujioka, K. Milashi, K. Mizuki, L.M. Cosentino, K.S. Fowke, L.M. Natschke, and K.-H. Lee Tetrahedron 57 2001 1559
10. G. Zeni, and R.C. Larock Chem. Rev. 104 2004 2285
11. J. Mori, M. Iwashima, M. Takeuchi, and H. Saito Chem. Pharm. Bull. 54 2006 391
12. J.H. Kwak, H.E. Kang, J.K. Jung, H. Kim, J. Cho, and H. Lee Arch. Pharmacal Res. 29 2006 728
13. B.M. Toste, and F.D. Toste J. Am. Chem. Soc. 120 1998 9074
14. R.S. Varma, and R. Dahiya J. Org. Chem. 63 1998 8038
15. K.C. Nicolaou, J.A. Pfefferkorn, and G.-Q. Cao Angew. Chem., Int. Ed. 39 2000 734
16. K.C. Nicolaou, G.-Q. Cao, and J.A. Pfefferkorn Angew. Chem., Int. Ed. 39 2000 739
17. H. Miao, and Z. Yang Org. Lett. 2 2000 1765
18. A. Maggiani, A. Tubul, and P. Brun Helv. Chem. Acta. 83 2000 650
19. Q. Wang, and M.G. Finn Org. Lett. 2 2000 4063 4065
20. G.W. Kabalka, B. Venkataiah, and C. Das Bhaskar Synlett 2004 2194 2196
21. M. Iyer, and G.R. Trivedi Synth. Commun. 20 1990 1347
22. T. Hanamoto, K. Shindo, M. Matsuoka, Y. Kiguchi, and M. Kondo J. Chem. Soc., Perkin Trans. 1 2000 3082
23. P.T. Kaye, and X.W. Nocanda J. Chem. Soc., Perkin Trans. 1 2000 1331
24. K.A. Parker, and T.L. Mindt Org. Lett. 3 2001 3875
25. A. Zonouzi, M. Sadeghi Googheri, and P.S. Miralinaghi Org. Prep. Proced. Int. 40 2008 471
26. A. Zonouzi, M. Binjaz, H. Rahmani, and S.W. Ng Acta Cryst. E65 2009 o752
27. Zonouzi, A.; Rahmani, H.; Jahangiri, A.; Z. Kristallogr. New Cryst. Struct. 223, 155.
28. A. Zonouzi, Z. Izakain, and M. Binaiz Org. Prep. Proced. Int. 41 2009 543
29. A. Zonouzi, M. Binaiz, R. Mirzazadeh, M. Talebi, and S.W. Ng Heterocycles 81 2010 1271
30. D. Ramaiah, P.M. Scaria, D.R. Cyr, P.K. Das, and M.V. George J. Org. Chem. 53 9 1988 2016 2022
31. Mehdi Ghandi, Ali-Tabatabaei Ghomi, and Maciej Kubicki J. Org. Chem. 78 2013 2611
32. Joanna V. Gaden, Alpa K. Pancholi, and Michael Shilpman J. Org. Chem. 78 2013 4158
33. S.K. Rodrigo, and H. Guan J. Org. Chem. 77 2012 8303
34. R. Sharma, A.K. Pandey, and P.M.S. Chauhan Synlett 2012 2209
35. T.B. Nguyen, L. Ermolenko, and A. Al-Mourabit Org. Lett. 14 2012 4274
36. L. Zheng, J. Ju, Y. Bin, and R. Hua J. Org. Chem. 77 2012 5794
37. C.E. Meyet, C.J. Pierce, and C.H. Larsen Org. Lett. 14 2012 964
38. M. Adib, E. Sheikhi, and H.R. Bijanzadeh Synlett 2012 85
39. B.M. Trost Compr. Org. Synth. 2 1991 34
40. T.L. Gilchrist Heterocyclic Chem. 1992 181
41. M.B. Smith, and J. March Adv. Org. Chem. 2001 1225
42. C.L. Shi, D.Q. Shi, S.H. Kim, Z.B. Huang, S.J. Ji, and M. Ji Tetrahedron 64 2008 2425
43. A. Kumar, and R.A. Maurya Tetrahedron 63 2007 1946
44. B. Alcaide, P. Almendros, A. Luna, and M.R. Torres J. Org. Chem. 71 2006 4818
45. A.O. Hossein, R. Elham, and M.H. Majid J. Chem. Res. S 2006 246
46. M.S. Rasalkar, M.K. Potdar, S.S. Mohile, and M.M. Salunkhe J. Mol. Catal. A: Chem. 235 2005 267
47. A. Bogevig, N. Kumaragurubaran, K. Juhl, W. Zhuang, and K.A. Jorgensen Angew. Chem., Int. Ed. 41 2002 1790
48. CCDC 911855 contains the supplementary crystallographic data for this paper. This data can be obtained free of charge at www.ccdc.cam.ac.uk/conts/ retrieving.html.