Novel succinct routes to quinoxalines and 2-benzimidazolylquinoxalines via the Ugi reaction

Muhammad Ayaz; Zhigang Xu; Christopher Hulme

doi:10.1016/j.tetlet.2014.04.013

Novel succinct routes to quinoxalines and 2-benzimidazolylquinoxalines via the Ugi reaction

Muhammad Ayaz, Zhigang Xu, Christopher Hulme

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

34 Scopus citations

Abstract

This Letter reveals a unique, user-friendly, concise two-step, one-pot protocol for the synthesis of highly substituted quinoxalines. Conducting the Ugi reaction with appropriately functionalized classical Ugi reagents with subsequent acid treatment of the Ugi adduct affords collections of diversified quinoxalines in good to excellent yields. The methodology exploits what may be viewed as a 'convertible carboxylic acid', which in addition may be captured in an intramolecular sense to generate structurally complex 2- benzimidazolylquinoxalines in a mere two steps.

Original language	English (US)
Pages (from-to)	3406-3409
Number of pages	4
Journal	Tetrahedron Letters
Volume	55
Issue number	23
DOIs	https://doi.org/10.1016/j.tetlet.2014.04.013
State	Published - Jun 4 2014

Keywords

Acyl transfer
Benzimidazole
Post-condensation modifications
Quinoxaline
Ugi reaction

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

Access to Document

10.1016/j.tetlet.2014.04.013

Cite this

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title = "Novel succinct routes to quinoxalines and 2-benzimidazolylquinoxalines via the Ugi reaction",

abstract = "This Letter reveals a unique, user-friendly, concise two-step, one-pot protocol for the synthesis of highly substituted quinoxalines. Conducting the Ugi reaction with appropriately functionalized classical Ugi reagents with subsequent acid treatment of the Ugi adduct affords collections of diversified quinoxalines in good to excellent yields. The methodology exploits what may be viewed as a 'convertible carboxylic acid', which in addition may be captured in an intramolecular sense to generate structurally complex 2- benzimidazolylquinoxalines in a mere two steps.",

keywords = "Acyl transfer, Benzimidazole, Post-condensation modifications, Quinoxaline, Ugi reaction",

author = "Muhammad Ayaz and Zhigang Xu and Christopher Hulme",

note = "Funding Information: The authors thank the NIH (P41GM08619001) for financial support and S.A. Roberts for X-ray analyses.",

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T1 - Novel succinct routes to quinoxalines and 2-benzimidazolylquinoxalines via the Ugi reaction

AU - Ayaz, Muhammad

AU - Xu, Zhigang

AU - Hulme, Christopher

N1 - Funding Information: The authors thank the NIH (P41GM08619001) for financial support and S.A. Roberts for X-ray analyses.

PY - 2014/6/4

Y1 - 2014/6/4

N2 - This Letter reveals a unique, user-friendly, concise two-step, one-pot protocol for the synthesis of highly substituted quinoxalines. Conducting the Ugi reaction with appropriately functionalized classical Ugi reagents with subsequent acid treatment of the Ugi adduct affords collections of diversified quinoxalines in good to excellent yields. The methodology exploits what may be viewed as a 'convertible carboxylic acid', which in addition may be captured in an intramolecular sense to generate structurally complex 2- benzimidazolylquinoxalines in a mere two steps.

AB - This Letter reveals a unique, user-friendly, concise two-step, one-pot protocol for the synthesis of highly substituted quinoxalines. Conducting the Ugi reaction with appropriately functionalized classical Ugi reagents with subsequent acid treatment of the Ugi adduct affords collections of diversified quinoxalines in good to excellent yields. The methodology exploits what may be viewed as a 'convertible carboxylic acid', which in addition may be captured in an intramolecular sense to generate structurally complex 2- benzimidazolylquinoxalines in a mere two steps.

KW - Acyl transfer

KW - Benzimidazole

KW - Post-condensation modifications

KW - Quinoxaline

KW - Ugi reaction

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

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Novel succinct routes to quinoxalines and 2-benzimidazolylquinoxalines via the Ugi reaction

Abstract

Keywords

ASJC Scopus subject areas

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CCDC 992449: Experimental Crystal Structure Determination

CCDC 992230: Experimental Crystal Structure Determination

Cite this

Novel succinct routes to quinoxalines and 2-benzimidazolylquinoxalines via the Ugi reaction

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Datasets

CCDC 992449: Experimental Crystal Structure Determination

CCDC 992230: Experimental Crystal Structure Determination

Cite this