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
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
收藏
页码:2212 / 2216
页数:5
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