Ugi/Robinson-Gabriel reactions directed toward the synthesis of 2,4,5-trisubstituted oxazoles

Arthur Y. Shaw; Zhigang Xu; Christopher Hulme

doi:10.1016/j.tetlet.2012.02.030

Ugi/Robinson-Gabriel reactions directed toward the synthesis of 2,4,5-trisubstituted oxazoles

Arthur Y. Shaw, Zhigang Xu, Christopher Hulme

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37 Scopus citations

Abstract

This Letter discloses a novel concise synthesis of a series of 2,4,5-trisubstituted oxazoles via a tandem Ugi/Robinson-Gabriel sequence. Herein, 2,4-dimethoxybenzylamine 1 was used as an ammonia equivalent in combination with arylglyoxal 3 and supporting Ugi reagents, an isonitrile and carboxylic acid. As such the product of the acid treated Ugi intermediate is ideally configured to undergo a Robinson-Gabriel cyclodehydration reaction to yield the desired oxazole scaffold 5.

Original language	English (US)
Pages (from-to)	1998-2000
Number of pages	3
Journal	Tetrahedron Letters
Volume	53
Issue number	15
DOIs	https://doi.org/10.1016/j.tetlet.2012.02.030
State	Published - Apr 11 2012

Keywords

2,4,5-Trisubstituted oxazoles
Multicomponent reactions
Robinson-Gabriel reaction
Ugi reaction
Vilsmeier-Haack reaction

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2012.02.030

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title = "Ugi/Robinson-Gabriel reactions directed toward the synthesis of 2,4,5-trisubstituted oxazoles",

abstract = "This Letter discloses a novel concise synthesis of a series of 2,4,5-trisubstituted oxazoles via a tandem Ugi/Robinson-Gabriel sequence. Herein, 2,4-dimethoxybenzylamine 1 was used as an ammonia equivalent in combination with arylglyoxal 3 and supporting Ugi reagents, an isonitrile and carboxylic acid. As such the product of the acid treated Ugi intermediate is ideally configured to undergo a Robinson-Gabriel cyclodehydration reaction to yield the desired oxazole scaffold 5.",

keywords = "2,4,5-Trisubstituted oxazoles, Multicomponent reactions, Robinson-Gabriel reaction, Ugi reaction, Vilsmeier-Haack reaction",

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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 - Ugi/Robinson-Gabriel reactions directed toward the synthesis of 2,4,5-trisubstituted oxazoles

AU - Shaw, Arthur Y.

AU - Xu, Zhigang

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.

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N2 - This Letter discloses a novel concise synthesis of a series of 2,4,5-trisubstituted oxazoles via a tandem Ugi/Robinson-Gabriel sequence. Herein, 2,4-dimethoxybenzylamine 1 was used as an ammonia equivalent in combination with arylglyoxal 3 and supporting Ugi reagents, an isonitrile and carboxylic acid. As such the product of the acid treated Ugi intermediate is ideally configured to undergo a Robinson-Gabriel cyclodehydration reaction to yield the desired oxazole scaffold 5.

AB - This Letter discloses a novel concise synthesis of a series of 2,4,5-trisubstituted oxazoles via a tandem Ugi/Robinson-Gabriel sequence. Herein, 2,4-dimethoxybenzylamine 1 was used as an ammonia equivalent in combination with arylglyoxal 3 and supporting Ugi reagents, an isonitrile and carboxylic acid. As such the product of the acid treated Ugi intermediate is ideally configured to undergo a Robinson-Gabriel cyclodehydration reaction to yield the desired oxazole scaffold 5.

KW - 2,4,5-Trisubstituted oxazoles

KW - Multicomponent reactions

KW - Robinson-Gabriel reaction

KW - Ugi reaction

KW - Vilsmeier-Haack reaction

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Ugi/Robinson-Gabriel reactions directed toward the synthesis of 2,4,5-trisubstituted oxazoles

Abstract

Keywords

ASJC Scopus subject areas

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