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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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Publication details

The article was received on 30 Apr 2013, accepted on 25 Jun 2013 and first published on 25 Jun 2013


Article type: Paper
DOI: 10.1039/C3OB40900G
Citation: Org. Biomol. Chem., 2013,11, 6036-6046
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    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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