A Highly Flexible and Efficient
Ugi-Type Multicomponent Synthesis of Versatile N-Fused
Aminoimidazoles

Sankar K. Guchhait; Chetna Madaan; Balmukund S. Thakkar

doi:10.1055/s-0029-1216916

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Synthesis 2009(19): 3293-3300
DOI: 10.1055/s-0029-1216916

PAPER

A Highly Flexible and Efficient Ugi-Type Multicomponent Synthesis of Versatile N-Fused Aminoimidazoles

Sankar K. Guchhait*, Chetna Madaan, Balmukund S. Thakkar
Department of Medicinal Chemistry, National Institute of Pharmaceutical Education and Research (NIPER), Sector 67, S. A. S. Nagar, Punjab 160 062, India
Fax: +91(172)2214692; e-Mail: skguchhait@niper.ac.in;

Further Information

Publication History

Received 1 May 2009
Publication Date:
23 July 2009 (online)

Abstract
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Abstract

A microwave-promoted highly flexible and efficient Ugi-type multicomponent reaction of heterocyclic amidines with aldehydes and isocyanides catalyzed by zirconium(IV) chloride was developed. The general protocol offered the very reliable synthesis of a library of medicinally important, widely versatile N-fused aminoimidazoles in excellent yields. Poorly reactive heterocyclic amidines, functionally and sterically hindered aldehydes, which suffer as troublesome reactants in earlier described methods, were rendered as feasible substrates in this process. The efficient catalysis by ZrCl₄ in addition to the effect of microwave irradiation was found crucial for gaining superior flexibility and efficiency of the protocol.

Key words

multicomponent reaction - N-heterocycles - catalysis - zirconium(IV) chloride - microwave

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