Synthesis of Trisubstituted Oxazoles via Aryne Induced [2,3] Sigmatropic Rearrangement-Annulation Cascade

被引：11

作者：

Gaykar, Rahul N. ^{[1
]}

Deswal, Shiksha ^{[1
]}

Guin, Avishek ^{[1
]}

Bhattacharjee, Subrata ^{[1
]}

Biju, Akkattu T. ^{[1
]}

机构：

[1] Indian Inst Sci, Dept Organ Chem, Bangalore 560012, Karnataka, India

来源：

ORGANIC LETTERS | 2022年 / 24卷 / 23期

关键词：

2+2+1 CYCLOADDITION; EMPLOYING ARYNES; BENZYNE; DERIVATIVES; CYCLIZATION; ARYLATION; OXIDATION; UMPOLUNG; POTENT; ALLYL;

D O I：

10.1021/acs.orglett.2c01379

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A transition-metal-free, [2,3] sigmatropic rearrangement-annulation cascade of 2-substituted thio/amino acetonitriles with arynes allowing the synthesis of 2,4,5-trisubstituted oxazoles under mild conditions has been demonstrated. The key sulfur/nitrogen ylides were generated by the initial S/N arylation followed by proton transfer, which was followed by the selective [2,3] sigmatropic rearrangement involving the -CN moiety and a subsequent annulation to afford the desired products in reasonable yields.

引用

页码：4145 / 4150

页数：6

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