2,3-pihydro-1H-1,3-diazepin-2-ones: synthesis and novel rearrangements into pyrrole derivatives

被引：8
|
作者：
Fesenko, Anastasia A. [1 ]
Shutalev, Anatoly D. [1 ]
机构：
[1] Moscow State Univ Fine Chem Technol, Dept Organ Chem, Moscow 119571, Russia
来源：
TETRAHEDRON LETTERS | 2014年 / 55卷 / 08期
基金：
俄罗斯基础研究基金会;
关键词：
1H-1,3-Diazepin-2-ones; Ring contraction; 2,3-Dihydro-1H-pyrrol-2-ones; 1H-Pyrroles; Anti-aromaticity; RING EXPANSION; ANTIAROMATICITY; AROMATICITY; 1H-1,3-DIAZEPINES; CONTRACTION; PHOTOLYSIS; AZIDES; PATH;
D O I：
10.1016/j.tetlet.2014.01.037
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A novel synthesis of 2,3-dihydro-1H-1,3-diazepin-2-ones based on thermal elimination of methanol from 4-methoxy-2,3,4,5-tetrahydro-1H-1,3-diazepin-2-ones has been developed. The prepared dihydrodiazepinones underwent two new rearrangements under basic or acidic conditions to give the pyrrole derivatives, 3-(aminomethylene)-2,3-dihydro-1H-pyrrol-2-ones and 1-carbamoy1-1H-pyrroles, respectively. Plausible mechanisms for the rearrangements are proposed. (C) 2014 Elsevier Ltd. All rights reserved.
引用
收藏
页码：1416 / 1420
页数：5
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