Catalyst-free domino-Knoevenagel-hetero-Diels-Alder reaction of terminal alkynes in water: an efficient one-step synthesis of indole-annulated thiopyranobenzopyran derivatives

Tetrahedron Letters

Volumn 51, Issue 1, 2010, Pages 147-150

  Majumdar, K C ^a   Taher, Abu ^a   Ponra, Sudipta ^a  

^a UNIVERSITY OF KALYANI   (India)

Author keywords

1 Methylindoline 2 thione; Domino Knoevenagel hetero Diels Alder reaction; Unactivated alkyne; Water reaction

Indexed keywords

1 METHYLINDOLINE 2 THIONE; ALDEHYDE; ALKYNE; BENZOPYRAN DERIVATIVE; INDOLE; NITROGEN; O PROPARGYLATED SALICYLALDEHYDE; OXYGEN; SALICYLALDEHYDE; SULFUR; THIOPYRANOBENZOPYRAN DERIVATIVE; UNCLASSIFIED DRUG; WATER;

ANNULATION REACTION; ARTICLE; CATALYSIS; CATALYST; DIELS ALDER REACTION; KNOEVENAGEL CONDENSATION; METHODOLOGY; SYNTHESIS;

ALNUS;

EID: 70649107882     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.10.108     Document Type: Article

References (65)

1. Saxton J.E. Indoles (1983), Wiley-Interscience, New York
2. Sundberg R.J. The Chemistry of Indoles (1970), Academic Press, New York
3. Carle J.S., and Christophersen C. J. Org. Chem. 45 (1980) 1586-1589
4. Sakabe N., Sendo Y., Iijima I., and Ban Y. Tetrahedron Lett 30 (1969) 2527-2530
5. Ohmoto T., and Koike K. Chem. Pharm. Bull. 32 (1984) 170-173
6. Shimizu M., Ishikawa M., Komoda Y., Nkajima T., Yamaguchi K., and Yoneda N. Chem. Pharm. Bull. 32 (1984) 463-474
7. Yamanaka E., One M., Kasamatsu S., Aimi N., and Sakai S. Chem. Pharm. Bull. 32 (1984) 818-821
8. Taniguchi M., Anjiki T., Nakagawa M., and Hino T. Chem. Pharm. Bull. 32 (1984) 2544-2554
9. Hashimoto Y., Shudo K., and Okamoto T. Chem. Pharm. Bull. 32 (1984) 4300-4308
10. Nakashima Y., Kawashima Y., Amanuma F., Sota K., Tanaka A., and Kameyama T. Chem. Pharm. Bull. 32 (1984) 4271-4280
11. Kamijo S., and Yamamoto Y. J. Org. Chem. 68 (2003) 4764-4771
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) 2191-2203
13. Haider N., and Sotelo E. Chem. Pharm. Bull. 50 (2002) 1479-1483
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) 354-357
15. Endo Y., Shudo K., Faruhata K., Ogura H., Sakai S., Aimi N., Hitotsuyonagi Y., and Koyama Y. Chem. Pharm. Bull. 32 (1984) 358-361
16. Takada S., and Makisumi Y. Chem. Pharm. Bull. 32 (1984) 872-876
17. Takada S., Ishizuka N., Sasatani T., Makisumi Y., Jyoyama H., Hatakeyama H., Asanuma F., and Hirose K. Chem. Pharm. Bull. 32 (1984) 877-886
18. Boger D.L., and Weinreb S.M. Hetero Diels-Alder Methodology in Organic Synthesis (1987), Academic Press, New York 225
19. Majumdar K.C., Basu P.K., Mukhopadhyay P.P., Sarkar S., Ghosh S.K., and Biswas P. Tetrahedron 59 (2003) 2151-2157
20. Majumdar K.C., and Mukhopadhyay P.P. Synthesis (2003) 97-100
21. Ingal A.H. In: Boulton A.S., and McKillop A. (Eds). Comprehensive Heterocyclic Chemistry Vol. 3 (1984), Pergamon Press, Oxford 773
22. Talley J.J. J. Org. Chem. 50 (1985) 1695-1699
23. Inamoto N. Heteroat. Chem. 12 (2001) 183-194
24. Majumdar K.C., Kundu U.K., and Ghosh S.K. Org. Lett. 4 (2002) 2629-2631
25. Majumdar K.C., and Muhuri S. Synthesis (2006) 2725-2730
26. Jayashankaran J., Manian R.D.R.S., and Raghunathan R. Tetrahedron Lett. 47 (2006) 2265-2270
27. 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) 4648-4651
28. Majumdar K.C., and Alam S. J. Chem. Res. (2006) 281-285
29. Majumdar K.C., and Alam S. Org. Lett. 8 (2006) 4059-4062
30. Majumdar K.C., and Chattopadhyay S.K. Can. J. Chem. 84 (2006) 469-475
31. Majumdar K.C., and Samanta S.K. Synth. Commun. 36 (2006) 1299-1306
32. Majumdar K.C., Bandopadhyay A., and Biswas A. Tetrahedron 59 (2003) 5289-5293
33. Majumdar K.C., Kundu U.K., and Ghosh S. Perkin Trans. 1 (2002) 2139-2140
34. For a detailed report on the toxicity of tin reagents, see: Occupational Exposure to Organotin Compounds, US Department of Health, Education and Welfare: Washington, November, 1976.
35. Boyer I.J. Toxicology 55 (1989) 253-298
36. Majumdar K.C., Taher A., and Ray K. Tetrahedron Lett. 50 (2009) 3889-3891
37. Baudelle R., Melnyk P., Deprez B., and Tartar A. Tetrahedron 54 (1998) 4125-4140
38. Yamanaka M., Nishida A., and Nakagana M. Org. Lett. 2 (2000) 159-161
39. Deligny M., Carreaux F., Toupet L., and Carboni B. Adv. Synth. Catal. 345 (2003) 1215-1219
40. Yadav J.S., Reddy B.V.S., Sadashiv K., and Padmavani B. Adv. Synth. Catal. 346 (2004) 607-610
41. Berkessel A., Erturk E., and Laporte C. Adv. Synth. Catal. 348 (2006) 223-228
42. Tietze L.F., Ott C., Gerke K., and Buback M. Angew. Chem., Int. Ed. Engl. 32 (1993) 1485-1486
43. Tietze L.F. Chem. Rev. 96 (1996) 115-136
44. Tietze L.F., and Rackelmann N. Pure Appl. Chem. 76 (2004) 1967-1983
45. Tietze L.F., Brasche G., and Gericke K. Domino Reactions in Organic Synthesis (2006), Wiley-VCH
46. Manikandan S., Shanmugasundaram M., and Raghunathan R. Tetrahedron 58 (2002) 8957-8962
47. Yadav J.S., Reddy B.V.S., Narsimhaswamy D., Lakshmi P.N., Narsimulu K., Srinivasulu G., and Kunwar A.C. Tetrahedron Lett. 45 (2004) 3493-3497
48. Jimenez-Alonso S., Estevez-Braun A., Ravelo A.G., Zarate R., and Lopez M. Tetrahedron 63 (2007) 3066-3074
49. Ramesh E., and Raghunathan R. Tetrahedron Lett. 49 (2008) 1812-1817
50. Lee Y.R., and Xia L. Tetrahedron Lett. 49 (2008) 3283-3287
51. Jimenez-Alonso S., Chavez H., Estevez-Braun A., Ravelo A.G., Feresin G., and Tapia A. Tetrahedron 64 (2008) 8938-8942
52. Lee Y.R., Kim Y.M., and Kim S.H. Tetrahedron 65 (2009) 101-108
53. Desimoni G., Faita G., Righetti P., and Tacconi G. Tetrahedron 52 (1996) 12009-12018
54. Khoshkholgh M.J., Balalaie S., Bijanzadeh H.R., and Gross J.H. Synlett (2009) 55-58
55. Khoshkholgh M.J., Balalaie S., Bijanzadeh H.R., and Gross J.H. ARKIVOC ix (2009) 114-121
56. Khoshkholgh M.J., Balalaie S., Bijanzadeh H.R., Rominger F., and Gross J.H. Tetrahedron Lett. 49 (2008) 6965-6968
57. Khoshkholgh M.J., Balalaie S., Gleiter R., and Rominger F. Tetrahedron Lett. 49 (2008) 10924-10929
58. Khoshkholgh M.J., Lotfi M., Balalaie S., and Rominger F. Tetrahedron 65 (2009) 4228-4234
59. Bashiardes G., Safir I., Barbot F., and Laduranty J. Tetrahedron Lett. 45 (2004) 1567-1570
60. Grieco P.A. Organic Synthesis in Water (1998), Blacky Academic & Professional Publishers, London
61. Lindstrom U.M. Chem. Rev. 102 (2002) 2751-2772
62. Li C.-J. Chem. Rev. 105 (2005) 3095-3165
63. Li C.J., and Chan T.H. Comprehensive Organic Reactions in Aqueous Media (2007), Wiley and Sons, New York
64. Dai J., Munakata M., Wu L.-P., Sowa T.K., and Suenaga Y. Inorg. Chim. Acta 258 (1997) 65-69
65. 23NOS: C, 76.42; H, 6.41; N, 3.87. Found: C, 76.54; H, 6.44; N, 3.76.