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

Organic & Biomolecular Chemistry Pub Date: 2013-06-25 DOI: 10.1039/C3OB40900G

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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