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通过 DBU 介导的环扩张反应,从给体-受体环丙烷直接合成高官能化呋喃。

Direct synthesis of highly functionalized furans from donor-acceptor cyclopropanes via DBU-mediated ring expansion reactions.

机构信息

School of Chemistry and Chemical Engineering, Yangzhou University, 180 Siwangting Street, Yangzhou 225002, PR China.

出版信息

Org Biomol Chem. 2019 Aug 7;17(31):7342-7351. doi: 10.1039/c9ob01308c.

Abstract

A DBU-mediated, unprecedented formal ring expansion reaction of 2-acyl-3-arylcyclopropane-1,1-dicarbonitriles for the synthesis of multisubstituted furan derivatives is reported. This transformation represents the regioselective ring-opening reaction of cyclopropane-1,1-dicarbonitriles and annulation using an intramolecular addition cascade reaction protocol for the synthesis of fully substituted furans includes use of readily available starting materials, mild reaction conditions, and it is transition-metal catalyst free, has good functional tolerance, and broad substrate scope.

摘要

本文报道了一种通过 DBU 介导的、前所未有的 2-酰基-3-芳基环丙基-1,1-二氰基的形式环扩大反应,用于合成多取代呋喃衍生物。这种转化代表了环丙烷-1,1-二氰基的区域选择性开环反应和利用分子内加成级联反应方案的环化反应,用于合成完全取代的呋喃,包括使用易得的起始原料、温和的反应条件、无过渡金属催化剂、具有良好的功能耐受性和广泛的底物范围。

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