Synthesis of peptidomimetics, δ- And ε-lactam tetrazoles

Steven Gunawan; Kristen Keck; Alex Laetsch; Christopher Hulme

doi:10.1007/s11030-012-9373-2

Synthesis of peptidomimetics, δ- And ε-lactam tetrazoles

Steven Gunawan, Kristen Keck, Alex Laetsch, Christopher Hulme

Research output: Contribution to journal › Article › peer-review

15 Scopus citations

Abstract

A concise two-step procedure for the synthesis of novel δ-lactam tetrazoles has been established via the Ugi-azide reaction using 5-oxohexanoic acid along with primary amines, isocyanides, and azidotrimethylsilane followed by 1,1′-carbonyldiimidazole-mediated intramolecular amide formation. Expansion to ε-lactam tetrazole scaffolds was accomplished using methyl 6-oxoheptanoate via the same Ugi-azide reaction followed by basic hydrolysis and SOCl₂ activation to enable lactam formation.

Original language	English (US)
Pages (from-to)	601-606
Number of pages	6
Journal	Molecular Diversity
Volume	16
Issue number	3
DOIs	https://doi.org/10.1007/s11030-012-9373-2
State	Published - Aug 2012

Keywords

1,5-disubstitutedtetrazoles
Multi-component reactions (MCRs)
Ugi reaction

ASJC Scopus subject areas

Catalysis
Information Systems
Molecular Biology
Drug Discovery
Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry

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10.1007/s11030-012-9373-2

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abstract = "A concise two-step procedure for the synthesis of novel δ-lactam tetrazoles has been established via the Ugi-azide reaction using 5-oxohexanoic acid along with primary amines, isocyanides, and azidotrimethylsilane followed by 1,1′-carbonyldiimidazole-mediated intramolecular amide formation. Expansion to ε-lactam tetrazole scaffolds was accomplished using methyl 6-oxoheptanoate via the same Ugi-azide reaction followed by basic hydrolysis and SOCl2 activation to enable lactam formation.",

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AU - Gunawan, Steven

AU - Keck, Kristen

AU - Laetsch, Alex

AU - Hulme, Christopher

N1 - Funding Information: Acknowledgments The authors thank the National Institute of Health (P41GM086190) for funding and Nicole Schechter for proof-reading.

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AB - A concise two-step procedure for the synthesis of novel δ-lactam tetrazoles has been established via the Ugi-azide reaction using 5-oxohexanoic acid along with primary amines, isocyanides, and azidotrimethylsilane followed by 1,1′-carbonyldiimidazole-mediated intramolecular amide formation. Expansion to ε-lactam tetrazole scaffolds was accomplished using methyl 6-oxoheptanoate via the same Ugi-azide reaction followed by basic hydrolysis and SOCl2 activation to enable lactam formation.

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KW - Ugi reaction

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Synthesis of peptidomimetics, δ- And ε-lactam tetrazoles

Abstract

Keywords

ASJC Scopus subject areas

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