Mechanistic studies leading to a new procedure for rapid, microwave assisted generation of pyridine-3,5-dicarbonitrile libraries

Kai Guo; Mark J. Thompson; Tummala R.K. Reddy; Roger Mutter; Beining Chen

doi:10.1016/j.tet.2007.03.139

Mechanistic studies leading to a new procedure for rapid, microwave assisted generation of pyridine-3,5-dicarbonitrile libraries

Kai Guo, Mark J. Thompson, Tummala R.K. Reddy, Roger Mutter, Beining Chen

University of Sheffield

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

46 Scopus citations

Abstract

Mechanistic investigations into the multi-component synthesis of pyridine-3,5-dicarbonitriles have established a defined reaction pathway, particularly clarifying the role of aerobic oxidation in conversion of the intermediate 1,4-dihydropyridines into the final products. Based on such improved understanding of the reaction mechanism, optimised conditions for the preparation of compound libraries based on this core structure have been developed and represent a significant improvement in yield over existing protocols. Particularly, microwave assisted synthesis was found to provide a procedure suitable for high-throughput synthesis of pyridine-3,5-dicarbonitrile libraries.

Original language	English
Pages (from-to)	5300-5311
Number of pages	12
Journal	Tetrahedron
Volume	63
Issue number	24
DOIs	https://doi.org/10.1016/j.tet.2007.03.139
State	Published - 11 Jun 2007
Externally published	Yes

Keywords

Aerobic oxidation
Drug-like molecules
Library synthesis
Mechanistic study
Microwave assisted reactions
Pyridine-3,5-dicarbonitriles

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10.1016/j.tet.2007.03.139

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abstract = "Mechanistic investigations into the multi-component synthesis of pyridine-3,5-dicarbonitriles have established a defined reaction pathway, particularly clarifying the role of aerobic oxidation in conversion of the intermediate 1,4-dihydropyridines into the final products. Based on such improved understanding of the reaction mechanism, optimised conditions for the preparation of compound libraries based on this core structure have been developed and represent a significant improvement in yield over existing protocols. Particularly, microwave assisted synthesis was found to provide a procedure suitable for high-throughput synthesis of pyridine-3,5-dicarbonitrile libraries.",

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AU - Guo, Kai

AU - Thompson, Mark J.

AU - Reddy, Tummala R.K.

AU - Mutter, Roger

AU - Chen, Beining

PY - 2007/6/11

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N2 - Mechanistic investigations into the multi-component synthesis of pyridine-3,5-dicarbonitriles have established a defined reaction pathway, particularly clarifying the role of aerobic oxidation in conversion of the intermediate 1,4-dihydropyridines into the final products. Based on such improved understanding of the reaction mechanism, optimised conditions for the preparation of compound libraries based on this core structure have been developed and represent a significant improvement in yield over existing protocols. Particularly, microwave assisted synthesis was found to provide a procedure suitable for high-throughput synthesis of pyridine-3,5-dicarbonitrile libraries.

AB - Mechanistic investigations into the multi-component synthesis of pyridine-3,5-dicarbonitriles have established a defined reaction pathway, particularly clarifying the role of aerobic oxidation in conversion of the intermediate 1,4-dihydropyridines into the final products. Based on such improved understanding of the reaction mechanism, optimised conditions for the preparation of compound libraries based on this core structure have been developed and represent a significant improvement in yield over existing protocols. Particularly, microwave assisted synthesis was found to provide a procedure suitable for high-throughput synthesis of pyridine-3,5-dicarbonitrile libraries.

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KW - Drug-like molecules

KW - Library synthesis

KW - Mechanistic study

KW - Microwave assisted reactions

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M3 - 文章

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JO - Tetrahedron

JF - Tetrahedron

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ER -

Mechanistic studies leading to a new procedure for rapid, microwave assisted generation of pyridine-3,5-dicarbonitrile libraries

Abstract

Keywords

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