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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
DMF-Assisted Radical Cyclization of o-Isocyanodiaryl Ethers via 1,5-Aryl Migration: Construction of
Sitian Yuan1, Xiaoling Ye1, Jingyu Cai1
1Key Laboratory for Green Chemistry of Jiangxi Province, Key Laboratory of Functional Small Molecules for Ministry of Education, Jiangxi Normal University, 99 Ziyang Avenue, Nanchang 330022, China.
Abstract:
A novel DMF-assisted radical cyclization of o-isocyanodiaryl ethers via 1,5-aryl migration has been developed for the synthesis of a series of 2-arylbenzoxazoles by the FeCl3/TBHP/Et3N catalytic system in DMF. However, N,N-dimethylbenzo[d]thiazole-2-carboxamide and N,N-dimethylbenzo[d]selenazole-2-carboxamide were obtained from the corresponding substrate 2-isocyanophenyl p-methoxyphenyl thioether and 2-isocyanodiphenyl selenoether under the same conditions. A possible mechanism may involve aryl 1,5-migration and DMF-assisted radical cyclization of o-isocyanodiaryl ethers.
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