DMF-Assisted Radical Cyclization of o-Isocyanodiaryl Ethers via 1,5-Aryl Migration: Construction of 2-Arylbenzoxazoles

被引：6

作者：

Yuan, Sitian ^{[1
]}

Ye, Xiaoling ^{[1
]}

Cai, Jingyu ^{[1
]}

Song, Zhibin ^{[1
]}

Tan, Yuxing ^{[1
]}

Peng, Yiyuan ^{[1
]}

Ding, Qiuping ^{[1
]}

机构：

[1] Jiangxi Normal Univ, Key Lab Green Chem Jiangxi Prov, Key Lab Funct Small Mol, Minist Educ, Nanchang 330022, Jiangxi, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2022年 / 87卷 / 02期

基金：

中国国家自然科学基金;

关键词：

METAL-FREE ARYLATION; BENZOXAZOLES; ISONITRILES; FORMAMIDES; SCAFFOLD;

D O I：

10.1021/acs.joc.1c02806

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：1485 / 1492

页数：8

共 3 条

[1] Carboxyl radical-assisted 1,5-aryl migration through Smiles rearrangement
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[2] Total synthesis of (±)-vinoxine: construction of the bridged pyrido[1,2-a]indole skeleton via Tf2O-mediated Bischler-Napieralski reaction and stereoselective radical cyclization
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[3] An expedient synthesis of indolo[1,2-α]quinolines via Mn(OAc)3-mediated oxidative free radical cyclization and NaI/O2-assisted dealkoxycarbonylation/aerobic oxidation cascade
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TETRAHEDRON LETTERS, 2010, 51 (38) : 5071 - 5075

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