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

24 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

Keywords

Amides
Copper
Homogeneous catalysis
Nitrogen heterocycles
Synthetic methods

ASJC Scopus subject areas

Physical and Theoretical Chemistry
Organic Chemistry

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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.",

keywords = "Amides, Copper, Homogeneous catalysis, Nitrogen heterocycles, Synthetic methods",

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

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T1 - Synthesis of 2,3-Disubstituted Quinazolinone Derivatives through Copper Catalyzed C-H Amidation Reactions

AU - Kotipalli, Trimurtulu

AU - Kavala, Veerababurao

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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