Stereoselective synthesis of novel annulated thiopyrano indole derivatives from simple oxindole via intramolecular 1,3-dipolar cycloaddition reactions of nitrone and nitrile oxide

Tetrahedron Letters

Volumn 53, Issue 7, 2012, Pages 762-764

  Majumder, Swarup ^a   Bhuyan, Pulak J ^a  

^a CSIR NORTH EAST INSTITUTE OF SCIENCE AND TECHNOLOGY   (India)

Author keywords

Halo aldehyde; 1,3 Dipolar cycloaddition reaction; Isoxazolidine; Oxindole; Stereoselective synthesis; Thiopyrano 2,3 b indole

Indexed keywords

INDOLE DERIVATIVE; ISOXAZOLE DERIVATIVE; ISOXAZOLIDINE DERIVATIVE; NITRILE OXIDE; NITRONE; OXINDOLE; THIOPYRAN DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLOADDITION; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 84855842407     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2011.11.136     Document Type: Article

References (44)

1. D.J. Faulkner Nat. Prod. Rep. 16 1999 155
2. M. Lounasmaa, and A. Tolvanen Nat. Prod. Rep. 17 2000 175
3. S. Takada, N. Ishizuka, T. Sasatani, Y. Makisumi, H. Jyoyama, H. Hatakeyama, F. Asanuma, and K. Hirose Chem. Pharm. Bull. 32 1984 877
4. S. Takada, and Y. Makisumi Chem. Pharm. Bull. 32 1984 872
5. G.B. Mullen, T.R. Decory, J.T. Mitchell, S.D. Allen, C.R. Kinssolving, and V.S. Georgiev J. Med. Chem. 31 1988 2008
6. M.J. Green, R.L. Tiberi, R. Friary, B.N. Lutsky, J. Berkenkoph, X. Fernandez, and M. Monahan J. Med. Chem. 25 1982 1492
7. R. Raunak, V. Kumar, S. Mukherjee, A.K. Poonam, K. Prasad, C.E. Olsen, S.J.C. Schaffer, S.K. Sharma, A.C. Watterson, W. Errington, and V.S. Parmar Tetrahedron 61 2005 5687
8. Y. Wu, G.F. Dai, J.H. Yang, Y.X. Zhang, Y. Zhu, and J.C. Tao Bioorg. Med. Chem. Lett. 19 2009 1818
9. A. Rescifina, M.A. Chiacchio, A. Corsaro, E. De Clercq, D. Iannazzo, A. Mastino, A. Piperno, G. Romeo, R. Romeo, and V. Valveri J. Med. Chem. 49 2006 709
10. G. Pandey, P. Banerjee, and S.R. Gadre Chem. Rev 106 2006 4484
11. K.V. Gothelf, and K.A. Jørgensen Chem. Rev. 98 1998 863
12. T. Mita, N. Ohtsuki, T. Ikeno, and T. Yamada Org. Lett. 4 2002 2457
13. B.E. Stephens, and F. Liu J. Org. Chem. 74 2009 254
14. J.C. Legeay, and N. Langlois J. Org. Chem. 72 2007 10108
15. W. Oppolzer, and H.P. Weber Tetrahedron Lett. 11 1970 1121
16. F. Busque, P. de March, M. Figueredo, J. Font, M. Monsalvatje, A. Virgili, A. Alvarez-Larena, and J.F. Piniella J. Org. Chem. 61 1996 8578
17. I. Coldham, and R. Hufton Chem. Rev. 105 2005 2765
18. A.H. Ingal A.S. Boulton, A. McKillop, Comprehensive Heterocyclic Chemistry Vol. 3 1984 Pergamon press Oxford 773
19. J.J. Talley J. Org. Chem. 50 1985 1695
20. D.L. Boger, and S.M. Weinreb Hetero Diels-AlderMethodology in Organic Synthesis 1987 Academic Press New York 225
21. N. Inamoto Heteroatom Chem. 12 2001 183
22. K.C. Majumdar, and M. Jana Synth. Commun. 37 2007 1375
23. K.C. Majumdar, P.K. Basu, P.P. Mukhopadhyay, S. Sarkar, S.K. Ghosh, and P. Biswas Tetrahedron 59 2003 2151
24. K.C. Majumdar, and P.P. Mukhopadhyay Synthesis 2003 97
25. J. Jayashankaran, R.D.R.S. Manian, and R. Raghunathan Tetrahedron Lett. 47 2006 2265
26. V.S. Matiychuk, R.B. Lesyk, M.D. Obushak, A. Gzella, D.V. Atamanyuk, Y.V. Ostapiuk, and A.P. Kryshchyshyn Tetrahedron Lett. 49 2008 4648
27. K.C. Majumdar, and S. Muhuri Synthesis 2006 2725
28. K.C. Majumdar, U.K. Kundu, and S.K. Ghosh Org. Lett. 4 2002 2629
29. K.C. Majumdar, A. Taher, and K. Ray Tetrahedron Lett. 50 2009 3889
30. T. Al-Nakib, V. Bezjak, S. Rashid, B. Fullam, and M.J. Meegan Eur. J. Med. Chem. 26 1991 221
31. T. Al-Nakib, V. Bezjak, M.J. Meegan, and R. Chandy Eur. J. Med. Chem. 25 1990 455
32. L.A. Van Vliet, N. Rodenhuis, D. Dijkstra, H. Wikstroem, T.A. Pugsley, K.A. Serpa, L.T. Meltzer, T.G. Heffner, L.D. Wise, M.E. Lajiness, R.M. Huff, K. Svensson, S. Sundell, and M. Lundmark J. Med. Chem. 43 2000 2871
33. A.R. Katritzky, and M.A.C. Button J. Org. Chem. 66 2001 5595
34. V.J. Ram, P. Srivastava, and A.S. Saxena J. Org. Chem. 66 2001 5333
35. M. Hori, T. Kataoka, H. Shimizu, E. Imai, N. Iwata, N. Kawamura, M. Kurono, K. Nakano, and M. Kido Chem. Pharm. Bull. 37 1989 1282
36. S. Majumder, and P.J. Bhuyan Synlett 2011 1547
37. B. Baruah, and P.J. Bhuyan Tetrahedron 65 2009 7099
38. M.L. Deb, S. Majumder, B. Baruah, and P.J. Bhuyan Synthesis 2010 929
39. M.L. Deb, and P.J. Bhuyan Synlett 2008 325
40. M.L. Deb, and P.J. Bhuyan Synthesis 2008 2891
41. S.C. Lu, X.Y. Duan, Z.J. Shi, B. Li, Y.W. Ren, W. Zhang, Y.H. Zhang, and Z.F. Tu Org. Lett. 11 2009 3902
42. S. Majumder, and P.J. Bhuyan Synlett 2 2011 173
43. E. Ceulemans, M. Voets, S. Emmers, K. Uytterhoeven, L.V. Meervelt, and W. Dehaen Tetrahedron 58 2002 531
44. U. Jacquemard, V. Beneteau, M. Lefoix, S. Routier, J.-Y. Merour, and G. Coudert Tetrahedron 60 2004 10039