Applications of ortho-phenylisonitrile and ortho-N-Boc aniline for the two-step preparation of novel bis-heterocyclic chemotypes

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

doi:10.1007/s11030-012-9374-1

Applications of ortho-phenylisonitrile and ortho-N-Boc aniline for the two-step preparation of novel bis-heterocyclic chemotypes

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

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

21 Scopus citations

Abstract

Concise routes to five pharmacologically relevant bis-heterocyclic scaffolds are described. Significant molecular complexity is generated in a mere two synthetic operations enabling access to each scaffold. Routes are often improved by microwave irradiation and all utilize isocyanide-based multi-component reaction methods to incorporate the required diversity elements. Common reagents in all initial condensation reactions include 2-(N-Boc-amino)-phenyl-isocyanide 1, mono-Boc-phenylenediamine 2 and ethyl glyoxalate 3.

Original language	English (US)
Pages (from-to)	607-612
Number of pages	6
Journal	Molecular Diversity
Volume	16
Issue number	3
DOIs	https://doi.org/10.1007/s11030-012-9374-1
State	Published - Aug 2012

Keywords

Benzimidazole-quinoxalines
Bis-benzimidazoles
Dihydroquinoxalinone
Multi-component reactions (MCRs)

ASJC Scopus subject areas

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

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10.1007/s11030-012-9374-1

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abstract = "Concise routes to five pharmacologically relevant bis-heterocyclic scaffolds are described. Significant molecular complexity is generated in a mere two synthetic operations enabling access to each scaffold. Routes are often improved by microwave irradiation and all utilize isocyanide-based multi-component reaction methods to incorporate the required diversity elements. Common reagents in all initial condensation reactions include 2-(N-Boc-amino)-phenyl-isocyanide 1, mono-Boc-phenylenediamine 2 and ethyl glyoxalate 3.",

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note = "Funding Information: Acknowledgments The authors would like to thank the NIH(5RC2 MH090878-02) for financial support and Nicole Schechter (PSM) for extensive copy editing.",

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doi = "10.1007/s11030-012-9374-1",

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AU - Xu, Zhigang

AU - Shaw, Arthur Y.

AU - Nichol, Gary S.

AU - Cappelli, Alexandra P.

AU - Hulme, Christopher

N1 - Funding Information: Acknowledgments The authors would like to thank the NIH(5RC2 MH090878-02) for financial support and Nicole Schechter (PSM) for extensive copy editing.

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AB - Concise routes to five pharmacologically relevant bis-heterocyclic scaffolds are described. Significant molecular complexity is generated in a mere two synthetic operations enabling access to each scaffold. Routes are often improved by microwave irradiation and all utilize isocyanide-based multi-component reaction methods to incorporate the required diversity elements. Common reagents in all initial condensation reactions include 2-(N-Boc-amino)-phenyl-isocyanide 1, mono-Boc-phenylenediamine 2 and ethyl glyoxalate 3.

KW - Benzimidazole-quinoxalines

KW - Bis-benzimidazoles

KW - Dihydroquinoxalinone

KW - Multi-component reactions (MCRs)

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Applications of ortho-phenylisonitrile and ortho-N-Boc aniline for the two-step preparation of novel bis-heterocyclic chemotypes

Abstract

Keywords

ASJC Scopus subject areas

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