New multi-component reaction accessing 3-aminoimidazo[1,2-a]pyridines

John Schwerkoske; Thierry Masquelin; Tom Perun; Christopher Hulme

doi:10.1016/j.tetlet.2005.09.181

New multi-component reaction accessing 3-aminoimidazo[1,2-a]pyridines

John Schwerkoske, Thierry Masquelin, Tom Perun, Christopher Hulme

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

73 Scopus citations

Abstract

The novel one step solution phase synthesis of an array of 3-aminoimidazo[1,2-a]pyridines is reported. Reactions were performed in methanol by mixing a α-amino-pyridine, aldehyde and trimethylsilylcyanide (TMSCN) to give the desired product. Mediated by microwave irradiation and catalyzed by scandium triflate, the methodology represents the first one pot preparation of 3-aminoimidazo[1,2-a]pyridines that avoids the use of an isonitrile and subsequent de-protection strategy. The reaction is an example of a formal three-centre-three-component multi-component reaction.

Original language	English (US)
Pages (from-to)	8355-8357
Number of pages	3
Journal	Tetrahedron Letters
Volume	46
Issue number	48
DOIs	https://doi.org/10.1016/j.tetlet.2005.09.181
State	Published - Nov 28 2005
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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abstract = "The novel one step solution phase synthesis of an array of 3-aminoimidazo[1,2-a]pyridines is reported. Reactions were performed in methanol by mixing a α-amino-pyridine, aldehyde and trimethylsilylcyanide (TMSCN) to give the desired product. Mediated by microwave irradiation and catalyzed by scandium triflate, the methodology represents the first one pot preparation of 3-aminoimidazo[1,2-a]pyridines that avoids the use of an isonitrile and subsequent de-protection strategy. The reaction is an example of a formal three-centre-three-component multi-component reaction.",

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AU - Schwerkoske, John

AU - Masquelin, Thierry

AU - Perun, Tom

AU - Hulme, Christopher

PY - 2005/11/28

Y1 - 2005/11/28

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AB - The novel one step solution phase synthesis of an array of 3-aminoimidazo[1,2-a]pyridines is reported. Reactions were performed in methanol by mixing a α-amino-pyridine, aldehyde and trimethylsilylcyanide (TMSCN) to give the desired product. Mediated by microwave irradiation and catalyzed by scandium triflate, the methodology represents the first one pot preparation of 3-aminoimidazo[1,2-a]pyridines that avoids the use of an isonitrile and subsequent de-protection strategy. The reaction is an example of a formal three-centre-three-component multi-component reaction.

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New multi-component reaction accessing 3-aminoimidazo[1,2-a]pyridines

Abstract

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