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Transition Metal-Free Cascade Reactions of Alkynols to Afford Isoquinolin-1(2H)-one and Dihydroisobenzofuran Derivatives

Author:
Li, Deng Yuan, Shi, Ke Ji, Mao, Xiao Feng, Chen, Guo Rong, Liu, Pei Nian
Source:
Journal of organic chemistry 2014 v.79 no.10 pp. 4602-4614
ISSN:
1520-6904
Subject:
aldehydes, amines, butanol, catalysts, chemical derivatives, fatty alcohols, imines, organic chemistry, solvents
Abstract:
Transition metal-free cascade reactions of alkynols with imines have been achieved using potassium tert-butoxide as catalyst. Switching the reaction solvent gives two kinds of products in good yield: isoquinolin-1(2H)-one derivatives and dihydroisobenzofuran derivatives. This approach was used to generate the natural product 8-oxypseudopalmatine in a two-step procedure from commercially available starting materials. Additionally, multicomponent reactions of alkynols, aldehydes, and amines were also successfully achieved to afford isoquinolin-1(2H)-one derivatives.
Agid:
5501398