Cyclization of o-Alkynylisocyanobenzenes with 1,3-Dicarbonyl Compounds

A facile and convenient reaction of o-alkynylisocyanobenzenes with various active-methylene compounds, including 1,3-diesters, 1,3-diketones, β-keto esters, and β-keto amides, under Brønsted basic conditions, has been developed. Diethyl malonate reacted smoothly with a collection of o-alkynylisocyan...

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Main Authors: Kannika La-Ongthong, Natthapat Sawekteeratana, Jasarin Klaysuk, Darunee Soorukram, Pawaret Leowanawat, Vichai Reutrakul, Sucheewin Krobthong, Patompon Wongtrakoongate, Chutima Kuhakarn
其他作者: Mahidol University
格式: Article
出版: 2022
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在線閱讀:https://repository.li.mahidol.ac.th/handle/123456789/73721
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機構: Mahidol University
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總結:A facile and convenient reaction of o-alkynylisocyanobenzenes with various active-methylene compounds, including 1,3-diesters, 1,3-diketones, β-keto esters, and β-keto amides, under Brønsted basic conditions, has been developed. Diethyl malonate reacted smoothly with a collection of o-alkynylisocyanobenzenes to provide the corresponding 2-quinolin-2-yl malonates in excellent yields. Acetylacetone gave a mixture of quinolin-4-yl and quinolin-2-yl derivatives. Acetoacetate esters and acetoacetyl amide derivative initially gave 2-quinolin-2-yl adducts that underwent partial deacetylation under the reaction conditions.