Studies on copper(I) catalysed cross-coupling reactions: A convenient and facile method for the synthesis of diversely substituted α,β-acetylenic ketones

Tetrahedron

Volumn 55, Issue 22, 1999, Pages 7011-7016

  Chowdhury, Chinmay ^a   Kundu, Nitya G ^a  

^a DEPARTMENT OF MATERIALS SCIENCE   (India)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE; CHLORIDE; COPPER; IODIDE; KETONE;

ARTICLE; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL REACTION; PRIORITY JOURNAL; REACTION ANALYSIS; SYNTHESIS; TEMPERATURE;

EID: 0033612113     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(99)00329-4     Document Type: Article

References (42)

1. A part of the results appeared as a preliminary communication : Chowdhury, C.; Kundu, N.G. Tetrahedron Lett., 1996, 37, 7323-7324; corrigendum : Chowdhury, C.; Kundu, N.G. Tetrahedron Lett., 1997, 38, 1863.
2. A part of the results appeared as a preliminary communication : Chowdhury, C.; Kundu, N.G. Tetrahedron Lett., 1996, 37, 7323-7324; corrigendum : Chowdhury, C.; Kundu, N.G. Tetrahedron Lett., 1997, 38, 1863.
3. (a) Okuro, K.; Furuune, M.; Enna, M; Miura, M.; Nomura, M. J. Org. Chem., 1993, 58, 4716-4721;
4. (b) Jeffery, T. J. Chem. Soc., Chem. Commun., 1988, 909-910;
5. (c) Jeffery, T. Tetrahedron Lett., 1989, 30, 2225-2228;
6. (d) Alami, M. and Ferri, F. Tetrahedron Lett., 1996, 37, 2763-2766;
7. (e) Mignani, G.; Chevalier, C.; Grass, F.; Allmang, G.; Movel, D. Tetrahedron Lett., 1990, 31, 5161-5164.
8. (a) Faweett, C.H.; Firu, R.D.; Spencer, D.M. Physiological Plant Pathology, 1971, 1, 163.
9. (b) Imai, K. J. Pharm. Soc. (Japan) 1956, 76, 405.
10. (c) Drews, S.E.; Libenberg, R.W. EP 130 829, January 1985, Chem. Abstr. 1985, 103, 22381X.
11. Kundu, N.G.; Das, B.; Spears, C.P.; Majumder, A.; Kang, S.-I. J. Med. Chem. 1990, 33, 1975-1979.
12. (a) Kundu, N.G.; Dasgupta, S.K. J. Chem. Soc.; Perkin Trans. 1. 1993, 2657-2663;
13. (b) Kundu, N.G.; Mahanty, J.S. and Spears, C.P. Bioorganic and Medicinal Chemistry Lett. 1996, 6, 1497-1502.
14. Heidelberger, C. Pyrimidine and Pyrimidine Antimetabolites in Cancer Medicine; Holland, J.F.; Frei, E.; Eds.; Lea and Febiger : Philadelphia, 1984, pp. 801-824.
15. (a) Gupta, C.M.; Jones, G.H.; Moffat, J.G. J. Org. Chem. 1976, 41, 3000-3009;
16. (b) Tam, S.Y.-K.; Klein, R.S.; De las Haras F.G.; Fox, J.J. J. Org. Chem. 1979, 44, 4854-4862.
17. (a) Balsubramanian, K.K.; Selvaraj, S.; Venkataramani, P.S. Synthesis 1980, 29-30;
18. (b) Wagner, F. and Meier, H. Tetrahedron 1974, 30, 773-780.
19. (a) Utimoto, K.; Miwa, H.; Nozaki, H. Tetrahedron Lett. 1981, 22, 4277-4278;
20. (b) Okuro, K.; Furuune, M.; Miura, M.; Nomura, M. J. Org. Chem. 1992, 57, 4754-4756;
21. (c) Pflieger, D.; Muckensturm, B. Tetrahedron Lett. 1990, 31, 2299-2300.
22. (a) Birkofer, L.; Ritter, A.; Uhlenbrauck, H. Chem. Ber. 1963, 96, 3280-3288;
23. (b) Walton, D.R.M.; Waugh, F. J. Organomet. Chem. 1972, 37, 45-56.
24. (c) Chopard, P.A.; Searle, R.J.G. and Devitt, F.H. J. Org. Chem. 1965, 30, 1015-1019;
25. (d) Brown, H.C.; Racheria, U.S.; Singh, S.M. Tetrahedron Lett. 1984, 25, 2411-2414.
26. (a) Tohda, Y.; Sonogashira, K.; Hagihara, N. Synthesis 1977, 777-778;
27. (b) Arcadi, A.; Cacchi, S.; Marinelli, F.; Pace, P.; Sanzi, G. Synlett. 1995, 823-824;
28. (c) Negishi, E.-I.; Bagheri, V.: Chatterjee, S.; Luo, F.-T.; Miller, J.A.; Soll, A.T. Tetrahedron Lett. 1983, 24, 5181-5184.
29. (d) Logue, M. W.; Teng, K. J. Org. Chem. 1982, 47, 2549-2553.
30. Zanina, A.S.; Shergina, S.I.; Sokolov, I.E.; Kotlyarevskii, I.L. Izvestiya Akademii Nauk USSR, Seriya Khimicheskayo. 1981, No. 5, 1158-1159; Chem. Abstr. 1981, 95, 97276s.
31. Zanina, A.S.; Shergina, S.I.; Sokolov, I.E.; Kotlyarevskii, I.L. Izvestiya Akademii Nauk USSR, Seriya Khimicheskayo. 1981, No. 5, 1158-1159; Chem. Abstr. 1981, 95, 97276s.
32. Ramachandran, P.V.; Teodorovic, A.V.; Rangaishenvi, M.V.; Brown, H.C. J. Org. Chem. 1992, 57, 2379-2386.
33. (a) Chowdhury, C.; Kundu, N.G. J. Chem. Soc., Chem. Commun. 1996, 1067-1068;
34. (b) Chaudhuri, G.; Chowdhury, C.; Kundu, N.G. Synlett. 1998, 1273-1275;
35. (c) Mahanty, J.S.; De. M.; Das, P.; Kundu, N.G. Tetrahedron. 1997, 53, 13397-13418.
36. Jones, E.R.H.; McCombie, J.T. J. Chem. Soc. 1942, 733-735.
37. Kundu, N.G.; Schmitz, S.A. J. Heterocyclic Chem. 1982, 19, 463-464.
38. Vogel's Text Book of Practical Organic Chemistry, Longman Group Limited, London, 4th Edition, 1978, p. 838.
39. (a) Fukue, Y.; Oi, S. and Inoue, Y. J. Chem. Soc., Chem. Commun. 1994, 2091;
40. (b) Brandsma, L. Preparative Acetylenic Chemistry, Elsevier, Amsterdam, 1988.
41. (a) Kundu, N.G. : Pal, M.; and Chowdhury, C. J. Chem. Research 1993, 432-433.
42. (b) Kundu, N.G.; Pal. M.; Mahanty, J.S.; De, M. J. Chem. Soc.; Perkin Trans. 1. 1997, 2815-2820.