Synthesis of Differentially Substituted 2-Aminoimidazolidines via a Microwave-Assisted Tandem Staudinger/Aza-Wittig Cyclization

被引：22

作者：

Kumar, Rakesh ^{[1
]}

Ermolat'ev, Denis S. ^{[1
]}

Van der Eycken, Erik V. ^{[1
]}

机构：

[1] Univ Leuven KU Leuven, Dept Chem, LOMAC, B-3001 Louvain, Belgium

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2013年 / 78卷 / 11期

关键词：

ONE-POT SYNTHESIS; POTENTIAL CHIRAL SUPERBASES; ENANTIOSELECTIVE SYNTHESIS; MODIFIED GUANIDINES; CYCLIC GUANIDINES; DERIVATIVES; ALKALOIDS; CHEMISTRY; AFFINITY; BIOLOGY;

D O I：

10.1021/jo400481b

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new route for the construction of 2-aminoimidazolidines including analogues of the alpha(2) adrenergic agonist drug clonidine is elaborated. The key step is an intramolecular microwave-assisted Staudinger/aza-Wittig cyclization of an in situ generated urea intermediate (formed by the reaction of beta-amino azide and isocyanate) upon treatment with Bu3P or polymer-supported phosphine reagent, allowing the introduction of various substituents at the N1 and the 2-amino function. Furthermore, a useful one-pot Staudinger/aza-Wittig/Buchwald-Hartwig protocol leading to bicyclic guanidines has been elaborated.

引用

页码：5737 / 5743

页数：7

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