One-pot synthesis of novel ether-linked diisoxazole derivatives via sequential O-propargylation and 1,3-dipolar cycloaddition from 2-bromohomoallylic alcohols

Abstract

A simple and efficient, one-pot approach for the synthesis of ether-linked diisoxazole derivatives has been developed through sequential reactions, which includes O-propargylation of 2-bromohomoallylic alcohols with propargyl bromide in the presence of sodium hydride in THF, and 1,3-dipolar cycloaddition by the addition of hydroximinoyl chlorides and triethylamine. This protocol provides some advantages such as high regioselectivity, easy operation and good product yields with a wide scope of substrates under mild conditions.

Graphical Abstract

Keywords:

• Ether-linked diisoxazole derivatives
• O-propargylation reaction
• 1,3-dipolar cycloaddition
• 2-bromohomoallylic alcohols
• hydroximinoyl chlorides
• one-pot procedure

Additional information

Funding

We are grateful to the National Natural Science Foundation of China [No. 21762022], the Research Program of Jiangxi Province Department of Education [No. GJJ170934, GJJ160289, GJJ11380], the Opening Foundation of National Research Center for Carbohydrate Synthesis [No. GJDTZX-KF-201414] and the Opening Foundation of Key Laboratory of Functional Small Organic Molecule of Ministry of Education [No. KLFS-KF-201411] for their generous financial support.