Transition-Metal-Free Synthesis of Substituted Pyridines via Ring Expansion of 2-Allyl-2H-azirines

被引：93

作者：

Jiang, Yaojia ^{[1
]}

Park, Cheol-Min ^{[3
]}

Loh, Teck-Peng ^{[1
,2
]}

机构：

[1] Nanyang Technol Univ, Sch Phys & Math Sci, Div Chem & Biol Chem, Singapore 637616, Singapore

[2] Univ Sci & Technol China, Dept Chem, Hefei 230026, Anhui, Peoples R China

[3] UNIST, Dept Chem, UNIST Gil 50, Ulsan 689798, South Korea

来源：

ORGANIC LETTERS | 2014年 / 16卷 / 13期

关键词：

HIGHLY FUNCTIONALIZED PYRIDINES; DE-NOVO SYNTHESIS; POLYSUBSTITUTED PYRIDINES; REGIOSELECTIVE SYNTHESIS; 2+2+2 CYCLOADDITION; DIELS-ALDER; 2H-AZIRINES; ROUTE; ALKYNES; DERIVATIVES;

D O I：

10.1021/ol501010k

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new strategy to open the 2-allyl-2H-azirines by 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) promotion in metal-free conditions affording 1-azatrienes that in situ electrocyclize to the pyridines in good to excellent yields is reported. 1:22 The reaction displays a broad substrate scope and good tolerance to a variety of substituents including aryl, alkyl, and heterocyclic groups. In addition, one-pot synthesis of pyridines from oximes via in situ formation of 2H-azirines was achieved.

引用

页码：3432 / 3435

页数：4

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