Brønsted Acid-Catalyzed Formal (3+3)-Annulation of Propargylic (Aza)-para-Quinone Methides with 4-Hydroxycoumarins and 1,3-Dicarbonyl Compounds

Autor:	Xue-Tao Xu, Ai-Jun Ma, Zong-Wang Qiu, Jin-Bao Peng, Zhen-Sheng Jia, Na Feng, Ji-Yuan Du, Xiang-Zhi Zhang, Bao Qiong Li, Han-Peng Pan
Rok vydání:	2021
Předmět:	Annulation 010405 organic chemistry Chemistry Organic Chemistry Organic chemistry Para-quinone 010402 general chemistry Brønsted–Lowry acid–base theory 01 natural sciences Pyranocoumarins 0104 chemical sciences Catalysis
Zdroj:	The Journal of Organic Chemistry. 86:6075-6089
ISSN:	1520-6904 0022-3263
Popis:	Herein, we describe a highly effective 1,8-conjugate-addition-mediated formal (3+3)-annulation of (aza)-para-quinone methides in situ generated from propargylic alcohols with 4-hydroxycoumarins and 1,3-dicarbonyl compounds under the catalysis of a Bronsted acid. This methodology affords efficient and practical access to synthetically important and highly functionalized pyranocoumarins and pyrans in excellent yields under mild conditions. Importantly, these products exhibit impressive inhibitory activity toward α-glucosidase.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::2ae2431c9655b4617a25e3a5fe29def2 https://doi.org/10.1021/acs.joc.0c02844 Zobrazit plný text záznamu