Facile, novel two-step syntheses of benzimidazoles, bis-benzimidazoles, and bis-benzimidazole-dihydroquinoxalines

Zhigang Xu; Arthur Y. Shaw; Justin Dietrich; Alexandra P. Cappelli; Gary Nichol; Christopher Hulme

doi:10.1007/s11030-011-9354-x

Facile, novel two-step syntheses of benzimidazoles, bis-benzimidazoles, and bis-benzimidazole-dihydroquinoxalines

Zhigang Xu
, Arthur Y. Shaw
, Justin Dietrich
, Alexandra P. Cappelli
, Gary Nichol
, Christopher Hulme

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

34 Scopus citations

Abstract

Three scaffolds of benzimidazoles, bis-benzimidazoles, and bis-benzimidazole-dihydroquinoxalines were synthesized via Ugi/de-protection/ cyclization methodology. Benzimidazole forming ring closure was enabled under microwave irradiation in the presence of 10% TFA/DCE. The methodology demonstrates the utility of 2-(N-Boc-amino)-phenyl-isocyanide for the generation of new molecular diversity.

Original language	English (US)
Pages (from-to)	73-79
Number of pages	7
Journal	Molecular Diversity
Volume	16
Issue number	1
DOIs	https://doi.org/10.1007/s11030-011-9354-x
State	Published - Feb 2012

Keywords

Benzimidazoles
Bis-benzimidazole-dihydroquinoxalines
Bis-benzimidazoles
Multi-component reactions (MCRs)
UDC

ASJC Scopus subject areas

Catalysis
Information Systems
Molecular Biology
Drug Discovery
Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry

Access to Document

10.1007/s11030-011-9354-x

Cite this

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title = "Facile, novel two-step syntheses of benzimidazoles, bis-benzimidazoles, and bis-benzimidazole-dihydroquinoxalines",

abstract = "Three scaffolds of benzimidazoles, bis-benzimidazoles, and bis-benzimidazole-dihydroquinoxalines were synthesized via Ugi/de-protection/ cyclization methodology. Benzimidazole forming ring closure was enabled under microwave irradiation in the presence of 10\% TFA/DCE. The methodology demonstrates the utility of 2-(N-Boc-amino)-phenyl-isocyanide for the generation of new molecular diversity.",

keywords = "Benzimidazoles, Bis-benzimidazole-dihydroquinoxalines, Bis-benzimidazoles, Multi-component reactions (MCRs), UDC",

author = "Zhigang Xu and Shaw, \{Arthur Y.\} and Justin Dietrich and Cappelli, \{Alexandra P.\} and Gary Nichol and Christopher Hulme",

note = "Funding Information: Acknowledgments The authors would like to thank the NIH (5RC2MH090878-02) for financial support and Nicole Schechter, PSM, for extensive copy editing.",

year = "2012",

month = feb,

doi = "10.1007/s11030-011-9354-x",

language = "English (US)",

volume = "16",

pages = "73--79",

journal = "Molecular Diversity",

issn = "1381-1991",

publisher = "Springer Nature",

number = "1",

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T1 - Facile, novel two-step syntheses of benzimidazoles, bis-benzimidazoles, and bis-benzimidazole-dihydroquinoxalines

AU - Xu, Zhigang

AU - Shaw, Arthur Y.

AU - Dietrich, Justin

AU - Cappelli, Alexandra P.

AU - Nichol, Gary

AU - Hulme, Christopher

N1 - Funding Information: Acknowledgments The authors would like to thank the NIH (5RC2MH090878-02) for financial support and Nicole Schechter, PSM, for extensive copy editing.

PY - 2012/2

Y1 - 2012/2

N2 - Three scaffolds of benzimidazoles, bis-benzimidazoles, and bis-benzimidazole-dihydroquinoxalines were synthesized via Ugi/de-protection/ cyclization methodology. Benzimidazole forming ring closure was enabled under microwave irradiation in the presence of 10% TFA/DCE. The methodology demonstrates the utility of 2-(N-Boc-amino)-phenyl-isocyanide for the generation of new molecular diversity.

AB - Three scaffolds of benzimidazoles, bis-benzimidazoles, and bis-benzimidazole-dihydroquinoxalines were synthesized via Ugi/de-protection/ cyclization methodology. Benzimidazole forming ring closure was enabled under microwave irradiation in the presence of 10% TFA/DCE. The methodology demonstrates the utility of 2-(N-Boc-amino)-phenyl-isocyanide for the generation of new molecular diversity.

KW - Benzimidazoles

KW - Bis-benzimidazole-dihydroquinoxalines

KW - Bis-benzimidazoles

KW - Multi-component reactions (MCRs)

KW - UDC

UR - https://www.scopus.com/pages/publications/84862786388

UR - https://www.scopus.com/pages/publications/84862786388#tab=citedBy

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DO - 10.1007/s11030-011-9354-x

M3 - Article

C2 - 22237832

AN - SCOPUS:84862786388

SN - 1381-1991

VL - 16

SP - 73

EP - 79

JO - Molecular Diversity

JF - Molecular Diversity

IS - 1

ER -

Facile, novel two-step syntheses of benzimidazoles, bis-benzimidazoles, and bis-benzimidazole-dihydroquinoxalines

Abstract

Keywords

ASJC Scopus subject areas

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CCDC 941765: Experimental Crystal Structure Determination

CCDC 941766: Experimental Crystal Structure Determination

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Facile, novel two-step syntheses of benzimidazoles, bis-benzimidazoles, and bis-benzimidazole-dihydroquinoxalines

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Datasets

CCDC 941765: Experimental Crystal Structure Determination

CCDC 941766: Experimental Crystal Structure Determination

Cite this