Two-step syntheses of fused quinoxaline-benzodiazepines and bis-benzodiazepines

Zhigang Xu; Justin Dietrich; Arthur Y. Shaw; Christopher Hulme

doi:10.1016/j.tetlet.2010.06.116

Two-step syntheses of fused quinoxaline-benzodiazepines and bis-benzodiazepines

Zhigang Xu, Justin Dietrich, Arthur Y. Shaw, Christopher Hulme

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

28 Scopus citations

Abstract

A two-step solution phase synthesis employing a double UDC (Ugi/Deprotect/Cyclize) strategy has been utilized to obtain fused 6,7,6,6-quinoxalinone-benzodiazepines and 6,7,7,6-bis-benzodiazepines. Optimization of the methodology to produce these tetracyclic scaffolds was enabled by microwave irradiation, incorporation of trifluoroethanol as solvent, and the use of the convertible isocyanide, 4-tert-butyl cyclohexen-1-yl isocyanide.

Original language	English (US)
Pages (from-to)	4566-4569
Number of pages	4
Journal	Tetrahedron Letters
Volume	51
Issue number	34
DOIs	https://doi.org/10.1016/j.tetlet.2010.06.116
State	Published - Aug 25 2010

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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abstract = "A two-step solution phase synthesis employing a double UDC (Ugi/Deprotect/Cyclize) strategy has been utilized to obtain fused 6,7,6,6-quinoxalinone-benzodiazepines and 6,7,7,6-bis-benzodiazepines. Optimization of the methodology to produce these tetracyclic scaffolds was enabled by microwave irradiation, incorporation of trifluoroethanol as solvent, and the use of the convertible isocyanide, 4-tert-butyl cyclohexen-1-yl isocyanide.",

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

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AU - Xu, Zhigang

AU - Dietrich, Justin

AU - Shaw, Arthur Y.

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 - 2010/8/25

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AB - A two-step solution phase synthesis employing a double UDC (Ugi/Deprotect/Cyclize) strategy has been utilized to obtain fused 6,7,6,6-quinoxalinone-benzodiazepines and 6,7,7,6-bis-benzodiazepines. Optimization of the methodology to produce these tetracyclic scaffolds was enabled by microwave irradiation, incorporation of trifluoroethanol as solvent, and the use of the convertible isocyanide, 4-tert-butyl cyclohexen-1-yl isocyanide.

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Two-step syntheses of fused quinoxaline-benzodiazepines and bis-benzodiazepines

Abstract

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