A Photochemical One-Pot Three-Component Synthesis of Tetrasubstituted Imidazoles

被引：69
|
作者：
Pusch, Stefan [1 ]
Opatz, Till [1 ]
机构：
[1] Johannes Gutenberg Univ Mainz, Inst Organ Chem, D-55128 Mainz, Germany
来源：
ORGANIC LETTERS | 2014年 / 16卷 / 20期
关键词：
ISOXAZOLES; CYCLIZATIONS; EFFICIENT; DESIGN;
D O I：
10.1021/ol502667h
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Tetrasubstituted imidazoles can be formed in a photochemical one-pot synthesis from aldehydes, alpha-amino-nitriles, and isoxazoles. Condensation of the first two components produces alpha-(alkylideneamino)nitriles which react under basic conditions with the acylazirines formed in situ by photochemical ring transformation of the isoxazole component. This process includes an unusual cleavage of the C-2-C-3 bond of the acylazirine. the reaction mechanism was studied by DFT calculations.
引用
收藏
页码：5430 / 5433
页数：4
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