Synthesis of 2,4-Disubstituted Imidazoles via Nucleophilic Catalysis

Dmitrii A.  Shabalin; Jay J.  Dunsford; Simbarashe  Ngwerume; Alexandra R.  Saunders; Duncan Gill; Jason E.  Camp

doi:10.1055/s-0039-1690832

Synthesis of 2,4-Disubstituted Imidazoles via Nucleophilic Catalysis

Dmitrii A. Shabalin, Jay J. Dunsford, Simbarashe Ngwerume, Alexandra R. Saunders, Duncan Gill, Jason E. Camp

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

16 Citations (Scopus)

Abstract

A convergent, microwave-assisted protocol for the synthesis of disubstituted NH-imidazoles via nucleophilic catalysis is described. The substituted imidazoles are accessed via the intramolecular addition of a variety of amidoxime substrates to activated alkynes followed by a thermally induced rearrangement of the in situ generated O-vinylamidÂ-oxime species. The unprotected imidazoles contain an aryl group at the 2-position as well as an ester moiety at the 4-position.

Original language	English
Pages (from-to)	797-800
Number of pages	4
Journal	Synlett
Volume	31
Issue number	8
Early online date	18 Feb 2020
DOIs	https://doi.org/10.1055/s-0039-1690832
Publication status	Published - 28 May 2020

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title = "Synthesis of 2,4-Disubstituted Imidazoles via Nucleophilic Catalysis",

abstract = "A convergent, microwave-assisted protocol for the synthesis of disubstituted NH-imidazoles via nucleophilic catalysis is described. The substituted imidazoles are accessed via the intramolecular addition of a variety of amidoxime substrates to activated alkynes followed by a thermally induced rearrangement of the in situ generated O-vinylamid{\^A}-oxime species. The unprotected imidazoles contain an aryl group at the 2-position as well as an ester moiety at the 4-position.",

keywords = "nucleophilic catalysis, imidazole, heterocycles, microwave, 19 F NMR, rearrangement",

author = "Shabalin, {Dmitrii A.} and Dunsford, {Jay J.} and Simbarashe Ngwerume and Saunders, {Alexandra R.} and Duncan Gill and Camp, {Jason E.}",

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T1 - Synthesis of 2,4-Disubstituted Imidazoles via Nucleophilic Catalysis

AU - Shabalin, Dmitrii A.

AU - Dunsford, Jay J.

AU - Ngwerume, Simbarashe

AU - Saunders, Alexandra R.

AU - Gill, Duncan

AU - Camp, Jason E.

PY - 2020/5/28

Y1 - 2020/5/28

N2 - A convergent, microwave-assisted protocol for the synthesis of disubstituted NH-imidazoles via nucleophilic catalysis is described. The substituted imidazoles are accessed via the intramolecular addition of a variety of amidoxime substrates to activated alkynes followed by a thermally induced rearrangement of the in situ generated O-vinylamidÂ-oxime species. The unprotected imidazoles contain an aryl group at the 2-position as well as an ester moiety at the 4-position.

AB - A convergent, microwave-assisted protocol for the synthesis of disubstituted NH-imidazoles via nucleophilic catalysis is described. The substituted imidazoles are accessed via the intramolecular addition of a variety of amidoxime substrates to activated alkynes followed by a thermally induced rearrangement of the in situ generated O-vinylamidÂ-oxime species. The unprotected imidazoles contain an aryl group at the 2-position as well as an ester moiety at the 4-position.

KW - nucleophilic catalysis

KW - imidazole

KW - heterocycles

KW - microwave

KW - 19 F NMR

KW - rearrangement

UR - http://www.scopus.com/inward/record.url?scp=85084643734&partnerID=8YFLogxK

U2 - 10.1055/s-0039-1690832

DO - 10.1055/s-0039-1690832

M3 - Article

VL - 31

SP - 797

EP - 800

JO - Synlett

JF - Synlett

SN - 0936-5214

IS - 8

ER -

Synthesis of 2,4-Disubstituted Imidazoles via Nucleophilic Catalysis

Abstract

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