Synthesis of 2,3-Disubstituted Quinazolinone Derivatives through Copper Catalyzed C-H Amidation Reactions

Trimurtulu Kotipalli; Veerababurao Kavala; Donala Janreddy; Vijayalakshmi Bandi; Chun Wei Kuo; Ching Fa Yao

doi:10.1002/ejoc.201501552

Synthesis of 2,3-Disubstituted Quinazolinone Derivatives through Copper Catalyzed C-H Amidation Reactions

Trimurtulu Kotipalli, Veerababurao Kavala, Donala Janreddy, Vijayalakshmi Bandi, Chun Wei Kuo, Ching Fa Yao

Department of Chemistry

Research output: Contribution to journal › Article

22 Citations (Scopus)

Abstract

The synthesis of quinazolinone derivatives was achieved from 2-iodobenzamide derivatives and various benzylamines, allylamine, and cinnamylamine derivatives through a one-pot copper-catalyzed reaction. In this reaction, the amine component (benzylamine/allylamine/cinnamylamine) is N-arylated with 2-iodobenzamide derivatives through Ullman coupling, followed by an intramolecular C-H amidation in the presence of copper catalyst. Copper-catalyzed tandem-Ullman N-alkylation and intramolecular C-H amidation reaction protocol for the synthesis of 2-phenylquinazolinone and quinazolinone derivatives from N-substituted 2-iodo-benzamides and benzylamines, allyl, and cinnamylamine is achieved.

Original language	English
Pages (from-to)	1182-1193
Number of pages	12
Journal	European Journal of Organic Chemistry
Volume	2016
Issue number	6
DOIs	https://doi.org/10.1002/ejoc.201501552
Publication status	Published - 2016 Feb 1

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Keywords

Amides
Copper
Homogeneous catalysis
Nitrogen heterocycles
Synthetic methods

ASJC Scopus subject areas

Physical and Theoretical Chemistry
Organic Chemistry

Cite this

Kotipalli, T., Kavala, V., Janreddy, D., Bandi, V., Kuo, C. W., & Yao, C. F. (2016). Synthesis of 2,3-Disubstituted Quinazolinone Derivatives through Copper Catalyzed C-H Amidation Reactions. European Journal of Organic Chemistry, 2016(6), 1182-1193. https://doi.org/10.1002/ejoc.201501552

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abstract = "The synthesis of quinazolinone derivatives was achieved from 2-iodobenzamide derivatives and various benzylamines, allylamine, and cinnamylamine derivatives through a one-pot copper-catalyzed reaction. In this reaction, the amine component (benzylamine/allylamine/cinnamylamine) is N-arylated with 2-iodobenzamide derivatives through Ullman coupling, followed by an intramolecular C-H amidation in the presence of copper catalyst. Copper-catalyzed tandem-Ullman N-alkylation and intramolecular C-H amidation reaction protocol for the synthesis of 2-phenylquinazolinone and quinazolinone derivatives from N-substituted 2-iodo-benzamides and benzylamines, allyl, and cinnamylamine is achieved.",

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author = "Trimurtulu Kotipalli and Veerababurao Kavala and Donala Janreddy and Vijayalakshmi Bandi and Kuo, {Chun Wei} and Yao, {Ching Fa}",

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AU - Kotipalli, Trimurtulu

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AU - Janreddy, Donala

AU - Bandi, Vijayalakshmi

AU - Kuo, Chun Wei

AU - Yao, Ching Fa

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N2 - The synthesis of quinazolinone derivatives was achieved from 2-iodobenzamide derivatives and various benzylamines, allylamine, and cinnamylamine derivatives through a one-pot copper-catalyzed reaction. In this reaction, the amine component (benzylamine/allylamine/cinnamylamine) is N-arylated with 2-iodobenzamide derivatives through Ullman coupling, followed by an intramolecular C-H amidation in the presence of copper catalyst. Copper-catalyzed tandem-Ullman N-alkylation and intramolecular C-H amidation reaction protocol for the synthesis of 2-phenylquinazolinone and quinazolinone derivatives from N-substituted 2-iodo-benzamides and benzylamines, allyl, and cinnamylamine is achieved.

AB - The synthesis of quinazolinone derivatives was achieved from 2-iodobenzamide derivatives and various benzylamines, allylamine, and cinnamylamine derivatives through a one-pot copper-catalyzed reaction. In this reaction, the amine component (benzylamine/allylamine/cinnamylamine) is N-arylated with 2-iodobenzamide derivatives through Ullman coupling, followed by an intramolecular C-H amidation in the presence of copper catalyst. Copper-catalyzed tandem-Ullman N-alkylation and intramolecular C-H amidation reaction protocol for the synthesis of 2-phenylquinazolinone and quinazolinone derivatives from N-substituted 2-iodo-benzamides and benzylamines, allyl, and cinnamylamine is achieved.

KW - Amides

KW - Copper

KW - Homogeneous catalysis

KW - Nitrogen heterocycles

KW - Synthetic methods

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10.1002/ejoc.201501552