Preparation of some heterocyclic enones and ynones by isomerisation of the propargylic alcohols

Journal of Chemical Research

Volumn , Issue 7, 2009, Pages 459-464

  Erenler, Ramazan ^a,b   Uno, Masaharu ^c   Goud, Thirumani Venkateshwar ^b   Biellmanna, Jean François ^a  

^a INSTITUTE OF CHEMISTRY   (Taiwan)

^b GAZIOSMANPASA UNIVERSITY   (Turkey)

^c GAKUSHUIN UNIVERSITY   (Japan)

Author keywords

Enone; ynone; Heterocyclic; Isomerisation; Propargylic alcohol

Indexed keywords

EID: 69849083095     PISSN: 03082342     EISSN: None     Source Type: Journal    
DOI: 10.3184/030823409X464467     Document Type: Article

References (33)

1. J.A. Joule, K. Mills and G.F. Smith, Heterocylic chemistry, Chapman and Hall, London, 1995, Vol. 3, pp 72.
2. A. Agalwal, K. Srivastava, S.K. Puri and P.M.S. Chauhan, Bioorg. Med. Chem., 2005, 13, 6226.
3. S.A. Ward, P.G. Bray, M. Mungthin and S.R. Hawley, Ann. Trop. Med. Parasit., 1995,89,121.
4. R. Musiol, J. Jampilek, K. Kralova, D.R. Richardson, D. Kalinowski, B. Podeszwa, J. Finster, H. Niedbala, A. Palka and J. Polanski, Bioorg. Med. Chem., 2007, 15, 1280.
5. J.P. Michael, Nat. Prod. Rep., 2007,24,223.
6. V.V. Kouznetsov, L.v. Méndez and C.M.M. Gómez, Curr. Org. Chem., 2005,9, 141.
7. A. Kleeman, J. Engel, B. Kutscher and D. Reichert, Pharmaceutical substances. synthesis, patents, applications, Thieme: Stuttgart, Germany, 2001.
8. J. Noverty, C.H. Collins and F.W. Starts, J. Pharm. Sci., 1974,63, 1264.
9. R. Erenler and J.-F. Biellmann, Tetrahedron Lett., 2005,46,5683.
10. W. Nineham and R.A. Raphael, J. Chem. Soc., 1949,118.
11. T. Ishikawa, T. Mizuta, K. Hagiwara, T. Aikawa, T. Kudo and S. Seito, J. Org. Chem., 2003,68,3702.
12. A. Coelho, E. Sotelo, N. Fraiz, M. Yanez, R. Laguna, E. Cano and E. Ravina, Bioorg. Med. Chem. Lett., 2004, 14, 321.
13. A. Arcadi, S. Cacchi, F. Marinelli and D. Misiti, Tetrahedron Lett., 1988, 29, 1457.
14. M.K.E. Saiah and R. Pellicciari, Tetrahedron Lett., 1995,36,4497.
15. X. Lu, J. Ji, C. Guo and W. Shen, J. Organomet. Chem., 1992,428,259.
16. K. Tanaka, T. Shoji and M. Hirano, Eur. J. Org. Chem., 2007,2687.
17. B.M. Trost and R.C. Livingston, J. Amer. Chem. Soc., 1995, 117, 9586.
18. J.P. Sonye and K. Koide, Synth. Commun., 2006,36,599.
19. J.P. Sonye and K. Koide, J. Org. Chem., 2006,71,6254.
20. J.P. Sonye and K. Koide, J. Org. Chem., 2007, 72, 1846.
21. H. Yamabe, A. Mizuno, H. Kusama and N. Iwasawa, J. Am. Chem. Soc., 2005, 127, 3248.
22. R. Erenler and J.F. Biellmann, J. Chinese Chem. Soc., 2007,54, 103.
23. W.R. Benn,J. Org. Chem., 1968,33,3113.
24. E.J. Corey and S. Terashima, Tetrahedron Lett., 1972,13,1815.
25. H.J. Reich, M.J. Kelly, R.E. Olson and R.C. Holtan, Tetrahedron, 1983, 39,949.
26. C.D. Vandelwal, D.A. Vosberg and E. Sorensen, J. Org. Let., 2001, 3,4307.
27. M.R Sestrick, M. Miller and L.S. Hegedus, J. Amer. Chem. Soc., 1992, 114,4076.
28. G. Massiot, Bull. Soc. Chim. Belg., 1990,99,717.
29. J.P. Sonye and K. Koide, Org. Lett., 2006, 8, 199.
30. A. Kwnar, U.D. Phalgune and S.S. Pawar, J. Phys. Org. Chem., 2001, 14, 577.
31. I. Fleming and S.K. Patel, Tetrahedron Lett., 1981,22,2321.
32. I. Fleming, S.K. PatelandC.J. Urch,J. Chem. Soc., Perkin I, 1989, 115.
33. A.L.K.S. Shun, E.T. Chemick, S. Eisler and R.R. Tykwinski, J. Org. Chem., 2003,68, 1339.