Issue 36, 2013

Bifunctional building blocks in the Ugi-azide condensation reaction: a general strategy toward exploration of new molecular diversity

Abstract

1,5-Disubstituted tetrazoles are an important drug-like scaffold known for their ability to mimic the cis-amide bond conformation. The scaffold is readily accessible via substitution of the carboxylic acid component of the Ugi multi-component reaction (MCR) with TMSN3 in what is herein denoted the Ugi-azide reaction. This full paper presents a concise, novel, general strategy to access a plethora of new heterocylic scaffolds utilizing tethered aldo/keto-acids/esters in the Ugi-azide reaction followed by a ring closing event that generates novel highly complex bis-heterocyclic lactam-tetrazoles.

Graphical abstract: Bifunctional building blocks in the Ugi-azide condensation reaction: a general strategy toward exploration of new molecular diversity

Supplementary files

Article information

Article type
Paper
Submitted
30 Apr 2013
Accepted
25 Jun 2013
First published
25 Jun 2013

Org. Biomol. Chem., 2013,11, 6036-6046

Bifunctional building blocks in the Ugi-azide condensation reaction: a general strategy toward exploration of new molecular diversity

S. Gunawan and C. Hulme, Org. Biomol. Chem., 2013, 11, 6036 DOI: 10.1039/C3OB40900G

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