Vinylketene-enamine cyclocondensation: A new access to functionalized phenols

Tetrahedron Letters

Volumn 38, Issue 8, 1997, Pages 1397-1398

  Collomb, Didier ^a   Doutheau, Alain ^a  

^a UNIVERSITÉ DE LYON   (France)

Author keywords

[No Author keywords available]

Indexed keywords

PHENOL DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; IN VITRO STUDY; METHODOLOGY; REACTION ANALYSIS;

EID: 0031584904     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00034-8     Document Type: Article

References (16)

1. 1. For recent reviews see: a) Hyatt, J.A.; Raynolds, P.W. Ketene Cycloadditions, Org. React. 1994, 45, pp. 159-646.
2. b) Tidwell, T.T. Ketenes, Wiley: New-York, 1995.
3. 2. Danheiser, R.L.; Sard, H. J. Org. Chem. 1980, 45, 4810-4812.
4. 3. Barbaro, G.; Battaglia, A.; Giorgianni, P. J. Org. Chem. 1987, 52, 3289-3296.
5. 4. a) Hickmott, P.W.; Miles, G.J.; Sheppard, G.; Urbani, R.; Yoxall, C.T. J. Chem. Soc., Perkin Trans. 1 1973, 1514-1519.
6. b) Berge, J.M.; Rey, M.; Dreiding, A.S. Helv. Chim. Acta 1982, 65, 2230-2241.
7. 5. a) Andriamiadanarivo, R.; Pujol, B.; Chantegrel, B.; Deshayes, C.; Doutheau, A. Tetrahedron Lett. 1993, 34, 7923-7924.
8. b) Chen, Y.P.; Chantegrel, B.; Deshayes, C. Heterocycles 1995, 41, 175-186.
9. c) Collomb, D.; Deshayes, C.; Doutheau, A. Tetrahedron 1996, 52, 6665-6684.
10. d) Collomb, D.; Chantegrel, B.; Deshayes, C. Tetrahedron 1996, 52, 10455-10472.
11. 6. For the preparation of pyridones by reaction of iminoketenes with benzynes or vinylisocyanates with enamines, see respectively: Crabtree, H.E.; Smalley, R.K.; Suschitzky, H. J. Chem. Soc. (C) 1968, 2730-2733 , and Rigby, J.H.; Balasubramanian, N. J. Org. Chem. 1989, 54, 224-228. For the preparation of arylsilanes by reaction of trimethylsilyl-substituted vinylallenones with enamines, see: Wang, K.K.; Andemichael, Y.W.; Dhumrongvaraporn, S. Tetrahedron Lett. 1989, 30, 1311-1314.
12. 6. For the preparation of pyridones by reaction of iminoketenes with benzynes or vinylisocyanates with enamines, see respectively: Crabtree, H.E.; Smalley, R.K.; Suschitzky, H. J. Chem. Soc. (C) 1968, 2730-2733 , and Rigby, J.H.; Balasubramanian, N. J. Org. Chem. 1989, 54, 224-228. For the preparation of arylsilanes by reaction of trimethylsilyl-substituted vinylallenones with enamines, see: Wang, K.K.; Andemichael, Y.W.; Dhumrongvaraporn, S. Tetrahedron Lett. 1989, 30, 1311-1314.
13. 6. For the preparation of pyridones by reaction of iminoketenes with benzynes or vinylisocyanates with enamines, see respectively: Crabtree, H.E.; Smalley, R.K.; Suschitzky, H. J. Chem. Soc. (C) 1968, 2730-2733 , and Rigby, J.H.; Balasubramanian, N. J. Org. Chem. 1989, 54, 224-228. For the preparation of arylsilanes by reaction of trimethylsilyl-substituted vinylallenones with enamines, see: Wang, K.K.; Andemichael, Y.W.; Dhumrongvaraporn, S. Tetrahedron Lett. 1989, 30, 1311-1314.
14. 7. Taylor, E.C.; Davies, H.M.L., Tetrahedron Lett. 1983, 24, 5453-5456.
15. 8. The E stereochemistry of diazo compounds 1a,b or 1c is required in order to avoid either competitive electrocyclic ring closure of intermediate vinylketenes or rhodium-carbenoid insertion reaction.
16. 9. All new compounds gave spectral and analytical data in full agreement with proposed structures. General procedure: diazo compound 1 was refluxed in benzene (or dichloromethane in the case of 1d) in the presence of a catalytic amount (3% mol) of rhodium acetate until complete disappearance of starting material (5 to 20 mn). The reaction mixture was then cooled to room temperature and after the addition of a solution of enamine 3 (1.2 eq.) in the same solvent, stirred overnight. After solvent evaporation the crude product was purified by flash column chromatography on silicagel.