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布朗斯特酸催化的两组分串联缩合及环异构化反应合成6(2)-异喹啉酮

Brønsted acid-catalyzed two-component tandem condensation and cycloisomerization to 6(2)-isoquinolinones.

作者信息

Yang Fang, Wang Lin-Lin, Liu Yu-Hua, Wu Ke-Xin, Chen Zi-Sheng, Ji Kegong

机构信息

College 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

出版信息

RSC Adv. 2025 Mar 24;15(12):8913-8917. doi: 10.1039/d5ra01267h. eCollection 2025 Mar 21.

DOI:10.1039/d5ra01267h
PMID:40129638
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC11931502/
Abstract

An attractive Brønsted acid-catalyzed two-component reaction of 2-alkynyl-4-hydroxybenzaldehydes 1 and primary amines 2 to various 6(2)-isoquinolinones 3 has been developed. This catalytic system realized an efficient tandem condensation and cycloisomerization reaction to 6(2)-isoquinolinones 3 in good to excellent yields 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(2)-isoquinolinones.

摘要

已开发出一种有吸引力的布朗斯特酸催化的2-炔基-4-羟基苯甲醛1与伯胺2生成各种6(2)-异喹啉酮3的双组分反应。该催化体系实现了高效的串联缩合和环异构化反应，以良好至优异的产率生成6(2)-异喹啉酮3——一种一锅法合成，其中以直接的方式构建了两种不同类型的C-N键。值得注意的是，该反应耐受各种脂肪族、芳基取代的胺，包括手性氨基醇和氨基酸。这种方法的实用性使其成为构建各种6(2)-异喹啉酮的可行替代方法。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6760/11931502/89c628c06d90/d5ra01267h-s4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6760/11931502/f92180df999b/d5ra01267h-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6760/11931502/899753e1d052/d5ra01267h-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6760/11931502/362261400723/d5ra01267h-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6760/11931502/aaadc7d9c32a/d5ra01267h-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6760/11931502/7be28937509c/d5ra01267h-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6760/11931502/89c628c06d90/d5ra01267h-s4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6760/11931502/f92180df999b/d5ra01267h-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6760/11931502/899753e1d052/d5ra01267h-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6760/11931502/362261400723/d5ra01267h-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6760/11931502/aaadc7d9c32a/d5ra01267h-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6760/11931502/7be28937509c/d5ra01267h-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6760/11931502/89c628c06d90/d5ra01267h-s4.jpg

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