Concise preparation of novel tricyclic chemotypes: Fused hydantoin-benzodiazepines

Steven Gunawan; Gary S. Nichol; Shashi Chappeta; Justin Dietrich; Christopher Hulme

doi:10.1016/j.tetlet.2010.06.131

Concise preparation of novel tricyclic chemotypes: Fused hydantoin-benzodiazepines

Steven Gunawan, Gary S. Nichol, Shashi Chappeta, Justin Dietrich, Christopher Hulme

Pharmacology and Toxicology

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

18 Scopus citations

Abstract

The following article describes a concise synthesis of a collection of 4,5-dihydro-1H-benzo[e][1,4]diazepines fused to a hydantoin ring. Molecular complexity and biological relevance are high and structures are generated in a mere three steps, employing the Ugi reaction to assemble diversity reagents. The protocol represents a novel UDC (Ugi-deprotect-cyclize) strategy employed in the Ugi-5-component CO₂-mediated condensation, followed by further cyclization under basic conditions, to afford the fused hydantoin. Mechanistic caveats, dependent on the aldehydes of choice will be revealed and a facile oxidation of the final products to imidazolidenetriones is briefly discussed.

Original language	English (US)
Pages (from-to)	4689-4692
Number of pages	4
Journal	Tetrahedron Letters
Volume	51
Issue number	36
DOIs	https://doi.org/10.1016/j.tetlet.2010.06.131
State	Published - Sep 8 2010

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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title = "Concise preparation of novel tricyclic chemotypes: Fused hydantoin-benzodiazepines",

abstract = "The following article describes a concise synthesis of a collection of 4,5-dihydro-1H-benzo[e][1,4]diazepines fused to a hydantoin ring. Molecular complexity and biological relevance are high and structures are generated in a mere three steps, employing the Ugi reaction to assemble diversity reagents. The protocol represents a novel UDC (Ugi-deprotect-cyclize) strategy employed in the Ugi-5-component CO2-mediated condensation, followed by further cyclization under basic conditions, to afford the fused hydantoin. Mechanistic caveats, dependent on the aldehydes of choice will be revealed and a facile oxidation of the final products to imidazolidenetriones is briefly discussed.",

author = "Steven Gunawan and Nichol, {Gary S.} and Shashi Chappeta and Justin Dietrich 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 ). Abbott Laboratories are also thanked for a New Faculty Award to C.H.",

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AU - Gunawan, Steven

AU - Nichol, Gary S.

AU - Chappeta, Shashi

AU - Dietrich, Justin

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 ). Abbott Laboratories are also thanked for a New Faculty Award to C.H.

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Y1 - 2010/9/8

N2 - The following article describes a concise synthesis of a collection of 4,5-dihydro-1H-benzo[e][1,4]diazepines fused to a hydantoin ring. Molecular complexity and biological relevance are high and structures are generated in a mere three steps, employing the Ugi reaction to assemble diversity reagents. The protocol represents a novel UDC (Ugi-deprotect-cyclize) strategy employed in the Ugi-5-component CO2-mediated condensation, followed by further cyclization under basic conditions, to afford the fused hydantoin. Mechanistic caveats, dependent on the aldehydes of choice will be revealed and a facile oxidation of the final products to imidazolidenetriones is briefly discussed.

AB - The following article describes a concise synthesis of a collection of 4,5-dihydro-1H-benzo[e][1,4]diazepines fused to a hydantoin ring. Molecular complexity and biological relevance are high and structures are generated in a mere three steps, employing the Ugi reaction to assemble diversity reagents. The protocol represents a novel UDC (Ugi-deprotect-cyclize) strategy employed in the Ugi-5-component CO2-mediated condensation, followed by further cyclization under basic conditions, to afford the fused hydantoin. Mechanistic caveats, dependent on the aldehydes of choice will be revealed and a facile oxidation of the final products to imidazolidenetriones is briefly discussed.

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Concise preparation of novel tricyclic chemotypes: Fused hydantoin-benzodiazepines

Abstract

ASJC Scopus subject areas

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