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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.

SUBMITTER: Gunawan S

PROVIDER: S-EPMC3795786 | biostudies-literature | 2013 Sep

REPOSITORIES: biostudies-literature

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

Gunawan Steven S Hulme Christopher C

Organic & biomolecular chemistry 20130901 36

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 fol ...[more]

PMID: 23912086

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