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Published on: November 9, 2019
Brønsted acid-catalyzed two-component tandem condensation and cycloisomerization to 6(2H)-isoquinolinones
Fang Yang1, Lin-Lin Wang1, Yu-Hua Liu1
1College of Chemistry and Pharmacy, Northwest A&F University, Shaanxi Key Laboratory of Natural Products & Chemical Biology 3 Taicheng Road Yangling 712100 Shaanxi P. R. China jikegong@nwsuaf.edu.cn.
Abstract:
An attractive Brønsted acid-catalyzed two-component reaction of 2-alkynyl-4-hydroxybenzaldehydes 1 and primary amines 2 to various 6(2H)-isoquinolinones 3 has been developed. This catalytic system realized an efficient tandem condensation and cycloisomerization reaction to 6(2H)-isoquinolinones 3 in good to excellent yields via a one-pot synthesis, in which two different kinds of C-N bonds were constructed in a straightforward manner. Remarkably, the reaction tolerated various aliphatic, aryl-substituted amines, including chiral amino alcohols and amino acids. The practicality of this approach rendered it a viable alternative for the construction of various 6(2H)-isoquinolinones.
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