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Issue 36, 2013
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Bifunctional building blocks in the Ugi-azide condensation reaction: a general strategy toward exploration of new molecular diversity

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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

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Supplementary files

Article information


Submitted
30 Apr 2013
Accepted
25 Jun 2013
First published
25 Jun 2013

Org. Biomol. Chem., 2013,11, 6036-6046
Article type
Paper

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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