A NEW MULTICOMPONENT SYNTHESIS OF 1,2,3,4-TETRAHYDROQUINOLINES

Citation
R. Annunziata et al., A NEW MULTICOMPONENT SYNTHESIS OF 1,2,3,4-TETRAHYDROQUINOLINES, Tetrahedron, 53(28), 1997, pp. 9715-9726
Citations number
39
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
ISSN journal
00404020
Volume
53
Issue
28
Year of publication
1997
Pages
9715 - 9726
Database
ISI
SICI code
0040-4020(1997)53:28<9715:ANMSO1>2.0.ZU;2-I
Abstract
The synthesis of a variety of differently substituted 1,2,3,4-tetrahyd roquinolines by a new three-component reaction involving an imine (Ar- N=CHR), an a-branched and enolizable aldehyde ((RRCHCHO)-R-1-C-2), and a nucleophile (ROH, ArSH, ArNH2, H2O) is described. The in situ gener ation of the imine (that allows a four-component process), and the rea ctions of an enantiomerically pure imine and/or aldehyde were also stu died. A short discussion of the reaction mechanism is reported. (C) 19 97 Elsevier Science Ltd.