Selenium dioxide-mediated synthesis of α-ketoamides from arylglyoxals and secondary amines

Arthur Y. Shaw; Christine R. Denning; Christopher Hulme

doi:10.1016/j.tetlet.2012.05.136

Selenium dioxide-mediated synthesis of α-ketoamides from arylglyoxals and secondary amines

Arthur Y. Shaw, Christine R. Denning, Christopher Hulme

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

37 Scopus citations

Abstract

A facile and expeditious synthetic approach for the synthesis of α-ketoamides 3 is described. A series of α-ketoamides 3 was synthesized via reaction of selenium dioxide-mediated oxidative amidation between arylglyoxals 1 and secondary amines 2, and accelerated with microwave irradiation. Our findings indicate that constrained amines, such as piperazine and piperidine exhibit higher conversions for this transformation. This reaction was explored by synthesizing a series of α-ketoamides 3 from various arylglyoxals 1 with cyclic and acyclic secondary amines 2.

Original language	English (US)
Pages (from-to)	4151-4153
Number of pages	3
Journal	Tetrahedron Letters
Volume	53
Issue number	32
DOIs	https://doi.org/10.1016/j.tetlet.2012.05.136
State	Published - Aug 8 2012

Keywords

Arylglyoxals
Microwave-assisted
Selenium dioxide
α-Ketoamides

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2012.05.136

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title = "Selenium dioxide-mediated synthesis of α-ketoamides from arylglyoxals and secondary amines",

abstract = "A facile and expeditious synthetic approach for the synthesis of α-ketoamides 3 is described. A series of α-ketoamides 3 was synthesized via reaction of selenium dioxide-mediated oxidative amidation between arylglyoxals 1 and secondary amines 2, and accelerated with microwave irradiation. Our findings indicate that constrained amines, such as piperazine and piperidine exhibit higher conversions for this transformation. This reaction was explored by synthesizing a series of α-ketoamides 3 from various arylglyoxals 1 with cyclic and acyclic secondary amines 2.",

keywords = "Arylglyoxals, Microwave-assisted, Selenium dioxide, α-Ketoamides",

author = "Shaw, {Arthur Y.} and Denning, {Christine R.} and Christopher Hulme",

note = "Funding Information: We would like to thank the Office of the Director, NIH, and the National Institute of Mental Health for funding (1RC2MH090878-01). Particular thanks to N. Schechter (PSM) for copy editing. ",

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T1 - Selenium dioxide-mediated synthesis of α-ketoamides from arylglyoxals and secondary amines

AU - Shaw, Arthur Y.

AU - Denning, Christine R.

AU - Hulme, Christopher

N1 - Funding Information: We would like to thank the Office of the Director, NIH, and the National Institute of Mental Health for funding (1RC2MH090878-01). Particular thanks to N. Schechter (PSM) for copy editing.

PY - 2012/8/8

Y1 - 2012/8/8

N2 - A facile and expeditious synthetic approach for the synthesis of α-ketoamides 3 is described. A series of α-ketoamides 3 was synthesized via reaction of selenium dioxide-mediated oxidative amidation between arylglyoxals 1 and secondary amines 2, and accelerated with microwave irradiation. Our findings indicate that constrained amines, such as piperazine and piperidine exhibit higher conversions for this transformation. This reaction was explored by synthesizing a series of α-ketoamides 3 from various arylglyoxals 1 with cyclic and acyclic secondary amines 2.

AB - A facile and expeditious synthetic approach for the synthesis of α-ketoamides 3 is described. A series of α-ketoamides 3 was synthesized via reaction of selenium dioxide-mediated oxidative amidation between arylglyoxals 1 and secondary amines 2, and accelerated with microwave irradiation. Our findings indicate that constrained amines, such as piperazine and piperidine exhibit higher conversions for this transformation. This reaction was explored by synthesizing a series of α-ketoamides 3 from various arylglyoxals 1 with cyclic and acyclic secondary amines 2.

KW - Arylglyoxals

KW - Microwave-assisted

KW - Selenium dioxide

KW - α-Ketoamides

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Selenium dioxide-mediated synthesis of α-ketoamides from arylglyoxals and secondary amines

Abstract

Keywords

ASJC Scopus subject areas

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