Short solution phase preparation of fused azepine-tetrazoles via a UDC (Ugi/de-Boc/cyclize) strategy

Thomas Nixey; Michael Kelly; David Semin; Christopher Hulme

doi:10.1016/S0040-4039(02)00636-6

Short solution phase preparation of fused azepine-tetrazoles via a UDC (Ugi/de-Boc/cyclize) strategy

Thomas Nixey, Michael Kelly, David Semin, Christopher Hulme

Pharmacology and Toxicology

Research output: Contribution to journal › Article

66 Scopus citations

Abstract

A novel application of the TMSN₃ modified Ugi 4-component reaction is disclosed for the solution phase synthesis of fused azepine-tetrazole libraries. The reaction of a N-Boc-α-amino aldehyde, secondary amine, methyl isocyanoacetate and trimethylsilylazide in methanol, followed by acid treatment, proton scavenging and reflux affords bicyclic azepine-tetrazoles. This efficient protocol, producing products with three diversity points, can be used to generate arrays of biologically relevant small molecules for general and targeted screening.

Original language	English (US)
Pages (from-to)	3681-3684
Number of pages	4
Journal	Tetrahedron Letters
Volume	43
Issue number	20
DOIs	https://doi.org/10.1016/S0040-4039(02)00636-6
State	Published - May 13 2002

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ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

Cite this

Nixey, T., Kelly, M., Semin, D., & Hulme, C. (2002). Short solution phase preparation of fused azepine-tetrazoles via a UDC (Ugi/de-Boc/cyclize) strategy. Tetrahedron Letters, 43(20), 3681-3684. https://doi.org/10.1016/S0040-4039(02)00636-6

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10.1016/S0040-4039(02)00636-6