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Department of Medicinal Chemistry, National Institute of Pharmaceutical Education and Research (NIPER), S. A. S. Nagar, Mohali - 160062, India
; Fax: +91 (0)172 2214692
; Tel: +91 (0)172 2214683
Org. Biomol. Chem., 2012,10, 9271-9277
03 Sep 2012,
02 Oct 2012
First published online
02 Oct 2012
KF-mediated nucleophilic activation of TMSCN as a functional isonitrile equivalent establishes an efficient and chemoselective Ugi-type multicomponent reaction of a heterocyclic amidine and aldehyde with TMSCN in water. In this approach, the use of isocyanide is circumvented, known competing reactions are virtually eliminated, pure products are obtained by a non-chromatographic method, and therapeutically relevant and diverse N-fused 3-aminoimidazoles can be prepared from a wide variety of aldehydes and heterocyclic amidines. This reaction coupling with cascade cyclization provides various privileged tetracyclic heteroaromatic scaffolds.
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Organic & Biomolecular Chemistry
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