Synthesis of Polysubstituted 2-Aminoimidazoles via Alkene-Diamination of Guanidine with Conjugated α-Bromoalkenones

被引：14

作者：

Guchhait, Sankar K. ^{[1
]}

Hura, Neha ^{[1
]}

Shah, Archana P. ^{[1
]}

机构：

[1] NIPER, Dept Med Chem, Sector 67,SAS Nagar, Mohali 160062, Punjab, India

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2017年 / 82卷 / 05期

关键词：

INTRAMOLECULAR DIAMINATION; IMIDAZOLES; PALLADIUM; AMIDINES; HETEROCYCLES; ALKALOIDS; CHEMISTRY; OXIDATION; BROMIDE; KETONES;

D O I：

10.1021/acs.joc.6b03021

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A step-economical access to polysubstituted aminoimidazoles has been accomplished via alkene vicinal C-N bonds formation of 2-bromo-2-alkenones with guanidine avoiding its NH-protection/derivatization prerequisite for electronic modulation. The approach has excellent substrate scope, is amenable to diverse guanidine-containing substrates, and introduces distinctive substitutions/functionalities into aminoimidazole core. It is also applicable to preparation of fused-imidazoles. The reaction involves a tandem pathway of azaMichael addition, S(N)2, and a unique redox-neutral process, as evident by spectroscopic study and control experiments.

引用

页码：2745 / 2752

页数：8

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