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
收藏
页码：5737 / 5743
页数：7
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