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

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

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
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

Access to Document

10.1016/S0040-4039(02)00636-6

Cite this

@article{4ca01927dbb844bfab8990ec9465bfda,

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

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.",

author = "Thomas Nixey and Michael Kelly and David Semin and Christopher Hulme",

year = "2002",

month = may,

day = "13",

doi = "10.1016/S0040-4039(02)00636-6",

language = "English (US)",

volume = "43",

pages = "3681--3684",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Limited",

number = "20",

}

TY - JOUR

T1 - Short solution phase preparation of fused azepine-tetrazoles via a UDC (Ugi/de-Boc/cyclize) strategy

AU - Nixey, Thomas

AU - Kelly, Michael

AU - Semin, David

AU - Hulme, Christopher

PY - 2002/5/13

Y1 - 2002/5/13

N2 - 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.

AB - 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.

UR - http://www.scopus.com/inward/record.url?scp=0037071230&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0037071230&partnerID=8YFLogxK

U2 - 10.1016/S0040-4039(02)00636-6

DO - 10.1016/S0040-4039(02)00636-6

M3 - Article

AN - SCOPUS:0037071230

VL - 43

SP - 3681

EP - 3684

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 20

ER -

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

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this