MCRs reshaped into a switchable microwave-assisted protocol toward 5-aminoimidazoles and dihydrotriazines

Christan E. Bell; Arthur Y. Shaw; Fabio De Moliner; Christopher Hulme

doi:10.1016/j.tet.2013.11.035

MCRs reshaped into a switchable microwave-assisted protocol toward 5-aminoimidazoles and dihydrotriazines

Christan E. Bell, Arthur Y. Shaw, Fabio De Moliner, Christopher Hulme

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

29 Scopus citations

Abstract

A tunable microwave-assisted protocol for the synthesis of two biologically relevant families of heterocycles has been designed. Via a simple switch of reaction conditions, the same starting materials can be engaged in either an improved synthesis of the dihydrotriazine scaffold or a novel, first-in-class MCR to render the challenging 5-aminoimidazole nucleus in a single step. An additional first-in-class MCR is also reported utilizing guanidines to afford 2,5-aminoimidazoles.

Original language	English (US)
Pages (from-to)	54-59
Number of pages	6
Journal	Tetrahedron
Volume	70
Issue number	1
DOIs	https://doi.org/10.1016/j.tet.2013.11.035
State	Published - Jan 7 2014

Keywords

Imidazole
Multicomponent reaction
Strecker
Trimethylsilyl cyanide

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tet.2013.11.035

Cite this

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title = "MCRs reshaped into a switchable microwave-assisted protocol toward 5-aminoimidazoles and dihydrotriazines",

abstract = "A tunable microwave-assisted protocol for the synthesis of two biologically relevant families of heterocycles has been designed. Via a simple switch of reaction conditions, the same starting materials can be engaged in either an improved synthesis of the dihydrotriazine scaffold or a novel, first-in-class MCR to render the challenging 5-aminoimidazole nucleus in a single step. An additional first-in-class MCR is also reported utilizing guanidines to afford 2,5-aminoimidazoles.",

keywords = "Imidazole, Multicomponent reaction, Strecker, Trimethylsilyl cyanide",

author = "Bell, {Christan E.} and Shaw, {Arthur Y.} and {De Moliner}, Fabio and Christopher Hulme",

note = "Funding Information: The authors thank Dr. Sue Roberts for X-ray analyses and Dr. David Bishop for proofreading, editing, and preparing the final version of the text and figures. The National Institute of Health (NIH) is gratefully acknowledged for funding ( P41GM086190 ). ",

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AU - Bell, Christan E.

AU - Shaw, Arthur Y.

AU - De Moliner, Fabio

AU - Hulme, Christopher

N1 - Funding Information: The authors thank Dr. Sue Roberts for X-ray analyses and Dr. David Bishop for proofreading, editing, and preparing the final version of the text and figures. The National Institute of Health (NIH) is gratefully acknowledged for funding ( P41GM086190 ).

PY - 2014/1/7

Y1 - 2014/1/7

N2 - A tunable microwave-assisted protocol for the synthesis of two biologically relevant families of heterocycles has been designed. Via a simple switch of reaction conditions, the same starting materials can be engaged in either an improved synthesis of the dihydrotriazine scaffold or a novel, first-in-class MCR to render the challenging 5-aminoimidazole nucleus in a single step. An additional first-in-class MCR is also reported utilizing guanidines to afford 2,5-aminoimidazoles.

AB - A tunable microwave-assisted protocol for the synthesis of two biologically relevant families of heterocycles has been designed. Via a simple switch of reaction conditions, the same starting materials can be engaged in either an improved synthesis of the dihydrotriazine scaffold or a novel, first-in-class MCR to render the challenging 5-aminoimidazole nucleus in a single step. An additional first-in-class MCR is also reported utilizing guanidines to afford 2,5-aminoimidazoles.

KW - Imidazole

KW - Multicomponent reaction

KW - Strecker

KW - Trimethylsilyl cyanide

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MCRs reshaped into a switchable microwave-assisted protocol toward 5-aminoimidazoles and dihydrotriazines

Abstract

Keywords

ASJC Scopus subject areas

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CCDC 916049: Experimental Crystal Structure Determination

CCDC 916050: Experimental Crystal Structure Determination

Cite this

MCRs reshaped into a switchable microwave-assisted protocol toward 5-aminoimidazoles and dihydrotriazines

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Datasets

CCDC 916049: Experimental Crystal Structure Determination

CCDC 916050: Experimental Crystal Structure Determination

Cite this