Metal-Free [2+2+1] Annulation of Alkynes, Nitriles, and Oxygen Atoms: Iodine(III)-Mediated Synthesis of Highly Substituted Oxazoles

被引：106

作者：

Saito, Akio ^{[1
]}

Taniguchi, Akihiro ^{[2
]}

Kambara, Yui ^{[1
]}

Hanzawa, Yuji ^{[2
]}

机构：

[1] Tokyo Univ Agr & Technol, Div Appl Chem, Inst Engn, Koganei, Tokyo 1848588, Japan

[2] Shows Pharmaceut Univ, Lab Organ React Chem, Machida, Tokyo 1948543, Japan

来源：

ORGANIC LETTERS | 2013年 / 15卷 / 11期

关键词：

OXIDATIVE CYCLOISOMERIZATION; 2,5-DISUBSTITUTED OXAZOLES; THIAZOLE SYNTHESIS; INTERNAL ALKYNES; KETONES; THIOAMIDES; CHEMISTRY; TRIFLUOROMETHANESULFONATE; CYCLOCONDENSATION; CYCLOADDITION;

D O I：

10.1021/ol4009816

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The metal-free [2 + 2 +1] annulation of alkynes, nitriles, and O-atoms for the regioselective assembly of 2,4-disubstituted and 2,4,5-trisubstituted oxazole compounds has been achieved by the use of PhlO with TfOH or Tf2NH. The present reaction could be applied to a facile synthesis of an anti-inflammatory drug.

引用

页码：2672 / 2675

页数：4

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