Domino-Knoevenagel-hetero-Diels-Alder reactions: an efficient one-step synthesis of indole-annulated thiopyranobenzopyran derivatives

Tetrahedron Letters

Volumn 50, Issue 27, 2009, Pages 3889-3891

  Majumdar, K C ^a   Taher, Abu ^a   Ray, Krishanu ^a  

^a UNIVERSITY OF KALYANI   (India)

Author keywords

1 Methylindoline 2 thione; Domino intramolecular; Knoevenagel hetero Diels Alder reactions; O Allylated salicylaldehydes; One step synthesis

Indexed keywords

BENZOPYRAN DERIVATIVE; INDOLE DERIVATIVE; NITROGEN; OXYGEN; SULFUR;

ANNULATION REACTION; ARTICLE; CHEMICAL REACTION; DIELS ALDER REACTION; KNOEVENAGEL CONDENSATION; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SYNTHESIS; X RAY ANALYSIS;

ALNUS;

EID: 65549154786     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.04.054     Document Type: Article

References (59)

1. Sundberg R.J. The Chemistry of Indoles (1970), Academic Press, New York p 438
2. Sendo Y., Iijima I., and Ban Y. Tetrahedron Lett. 30 (1969) 2527
3. Saxton J.E. Indoles (1983), Wiely-Interscience, New York Part 4
4. Ohmoto T., and Koike K. Chem. Pharm. Bull. 32 (1984) 170
5. Shimizu M., Ishikawa M., Komoda Y., Nkajima T., Yamaguchi K., and Yoneda N. Chem. Pharm. Bull. 32 (1984) 463
6. Yamanaka E., One M., Kasamatsu S., Aimi N., and Sakai S. Chem. Pharm. Bull. 32 (1984) 818
7. Carle J.S., and Christophersen C. J. Org. Chem. 45 (1980) 1586
8. Taniguchi M., Anjiki T., Nakagawa M., and Hino T. Chem. Pharm. Bull. 32 (1984) 2544
9. Hashimoto Y., Shudo K., and Okamoto T. Chem. Pharm. Bull. 32 (1984) 4300
10. Kamijo S., and Yamamoto Y. J. Org. Chem. 68 (2003) 4764
11. Nakashima Y., Kawashima Y., Amanuma F., Sota K., Tanaka A., and Kameyama T. Chem. Pharm. Bull. 32 (1984) 4271
12. Guillonneare C., Pierre A., Charton Y., Guilbaud N., Kraus-Berthier I., Leonce S., Michel A., Bisagni I., and Atassi G. J. Med. Chem. 42 (1999) 2191
13. Haider N., and Sotero E. Chem. Pharm. Bull. 50 (2002) 1479
14. Sakai S., Aimi N., Yamaguchi K., Hitotsuyonagi Y., Watanabe C., Yokose K., Koyama Y., Shudo K., and Itai A. Chem. Pharm. Bull. 32 (1984) 354
15. Endo Y., Shudo K., Faruhata K., Ogura H., Sakai S., Aimi N., Hitotsuyonagi Y., and Koyama Y. Chem. Pharm. Bull. 32 (1984) 358
16. Takada S., Ishizuka N., Sasatani T., Makisumi Y., Jyoyama H., Hatakeyama H., Asanuma F., and Hirose K. Chem. Pharm. Bull. 32 (1984) 877
17. Takada S., and Makisumi Y. Chem. Pharm. Bull. 32 (1984) 872
18. Ingal A.H. In: Boulton A.S., and McKillop A. (Eds). Comprehensive Heterocyclic Chemistry Vol. 3 (1984), Pergamon Press, Oxford 773
19. Talley J.J. J. Org. Chem. 50 (1985) 1695
20. Boger D.L., and Weinreb S.M. Hetero Diels-Alder Methodology in Organic Synthesis (1987), Academic Press, New York 225
21. Inamoto N. Heteroatom. Chem. 12 (2001) 183
22. Majumdar K.C., and Jana M. Synth. Commun. 37 (2007) 1375
23. Majumdar K.C., Basu P.K., Mukhopadhyay P.P., Sarkar S., Ghosh S.K., and Biswas P. Tetrahedron 59 (2003) 2151
24. Majumdar K.C., and Mukhopadhyay P.P. Synthesis (2003) 97
25. Jayashankaran J., Manian R.D.R.S., and Raghunathan R. Tetrahedron Lett. 47 (2006) 2265
26. Matiychuk V.S., Lesyk R.B., Obushak M.D., Gzella A., Atamanyuk D.V., Ostapiuk Y.V., and Kryshchyshyn A.P. Tetrahedron Lett. 49 (2008) 4648
27. Majumdar K.C., and Muhuri S. Synthesis (2006) 2725
28. Majumdar K.C., Kundu U.K., and Ghosh S.K. Org. Lett. 4 (2002) 2629
29. Majumdar K.C., and Alam S. J. Chem. Res. (2006) 281
30. Majumdar K.C., and Alam S. Org. Lett. 8 (2006) 4059
31. Majumdar K.C., Islam R., and Alam S. Synth. Commun. 38 (2008) 754
32. Majumdar K.C., and Chattopadhyay S.K. Can. J. Chem. 84 (2006) 469
33. Majumdar K.C., and Samanta S.K. Synth. Commun. 36 (2006) 1299
34. Majumdar K.C., Kundu U.K., Mukhopadhyay P.P., and Ghosh S. Arkivoc 47 (2003)
35. Majumdar K.C., Bandopadhyay A., and Biswas A. Tetrahedron 59 (2003) 5289
36. Majumdar K.C., Kundu U.K., and Ghosh S. Perkin Trans. 1 (2002) 2139
37. For a detailed report on the toxicity of tin reagents, see Occupational Exposure to Organotin Compounds, US Department of Health, Education and Welfare, Washington, Nov. 1976.
38. Boyer I.J. Toxicology 55 (1989) 253
39. Yadav J.S., Reddy B.V.S., Sadashiv K., and Padmavani B. Adv. Synth. Catal. 346 (2004) 607
40. Yamanaka M., Nishida A., and Nakagana M. Org. Lett. 2 (2000) 159
41. Deligny M., Carreaux F., Toupet L., and Carboni B. Adv. Synth. Catal. 345 (2003) 1215
42. Berkessel A., Erturk E., and Laporte C. Adv. Synth. Catal. 348 (2006) 223
43. Baudelle R., Melnyk P., Deprez B., and Tartar A. Tetrahedron 54 (1998) 4125
44. Tietze L.F. Chem. Rev. 96 (1996) 115
45. Tietze L.F., Brasche G., and Gericke K. Domino Reactions in Organic Synthesis (2006), Wiley-VCH
46. Tietze L.F., and Rackelmann N. Pure Appl. Chem. 76 (2004) 1967
47. Tietze L.F., Ott C., Gerke K., and Buback M. Angew. Chem., Int. Ed. Engl. 32 (1993) 1485
48. Desimoni G., Faita G., Righetti P., and Tacconi G. Tetrahedron 52 (1996) 12009
49. Ramesh E., and Raghunathan R. Tetrahedron Lett. 49 (2008) 1812
50. Lee Y.R., and Xia L. Tetrahedron Lett. 49 (2008) 3283
51. Jimenez-Alonso S., Chavez H., Estevez-Braun A., Ravelo A.G., Feresin G., and Tapia A. Tetrahedron 64 (2008) 8938
52. Jimenez-Alonso S., Estevez-Braun A., Ravelo A.G., Zarate R., and Lopez M. Tetrahedron 63 (2007) 3066
53. Manikandan S., and Raghunathan R. Tetrahedron 58 (2002) 8957
54. Yadav J.S., Reddy B.V.S., Narsimhaswamy D., Lakshmi P.N., Narsimulu K., Srinivasulu G., and Kunwar A.C. Tetrahedron Lett. 45 (2004) 3493
55. Lee Y.R., Kim Y.M., and Kim S.H. Tetrahedron 65 (2009) 101
56. Gazith M., and Noys R.M. J. Am. Chem. Soc. 77 (1955) 6091
57. +: 308.1104; found; 308.1094.
58. CCDC reference no. for the CIF file of compound 4a: CCDC 719681.
59. Hoffmann R.W. Chem. Rev. 89 (1989) 1841