Synthesis of Pyridines by Carbenoid-Mediated Ring Opening of 2H-Azirines

被引：125

作者：

Loy, Nicole S. Y. ^{[1
]}

Singh, Alok ^{[1
]}

Xu, Xianxiu ^{[1
]}

Park, Cheol-Min ^{[1
]}

机构：

[1] Nanyang Technol Univ, Sch Phys & Math Sci, Div Chem & Biol Chem, Singapore 637371, Singapore

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2013年 / 52卷 / 08期

关键词：

carbenoids; electrocyclic reactions; heterocycle; ring expansion; synthetic methods; HIGHLY SUBSTITUTED PYRROLES; DIAZO OXIME ETHERS; DE-NOVO SYNTHESIS; 2+2+2 CYCLOADDITION; BOND ACTIVATION; DIELS-ALDER; DERIVATIVES; HETEROCYCLES; EXPANSION; INDOLES;

D O I：

10.1002/anie.201209301

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Roaming the range: The title reaction tolerates a wide range of substituents on the resulting pyridine ring using mild reaction conditions (see scheme; esp=α,α,α′,α′-tetramethyl-1,3- benzenedipropionic acid). The formation of the key intermediate is catalyst-controlled, and subsequent cyclization and oxidation affords pyridines in excellent yields. The method has been used for the efficient synthesis of polyarylpyridines. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：2212 / 2216

页数：5

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