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

Thomas Nixey, Michael Kelly, David Semin, Christopher Hulme

Research output: Contribution to journalArticle

66 Citations (Scopus)

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 languageEnglish (US)
Pages (from-to)3681-3684
Number of pages4
JournalTetrahedron Letters
Volume43
Issue number20
DOIs
StatePublished - May 13 2002
Externally publishedYes

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Tetrazoles
Azepines
Scavenging
Aldehydes
Libraries
Amines
Methanol
Protons
Screening
Molecules
Acids

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Short solution phase preparation of fused azepine-tetrazoles via a UDC (Ugi/de-Boc/cyclize) strategy. / Nixey, Thomas; Kelly, Michael; Semin, David; Hulme, Christopher.

In: Tetrahedron Letters, Vol. 43, No. 20, 13.05.2002, p. 3681-3684.

Research output: Contribution to journalArticle

Nixey, Thomas ; Kelly, Michael ; Semin, David ; Hulme, Christopher. / Short solution phase preparation of fused azepine-tetrazoles via a UDC (Ugi/de-Boc/cyclize) strategy. In: Tetrahedron Letters. 2002 ; Vol. 43, No. 20. pp. 3681-3684.
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