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^*

^*此作品的通信作者

化學系

研究成果: 雜誌貢獻 › 期刊論文 › 同行評審

54 引文斯高帕斯（Scopus）

摘要

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.

原文	英語
頁（從 - 到）	1182-1193
頁數	12
期刊	European Journal of Organic Chemistry
卷	2016
發行號	6
DOIs	https://doi.org/10.1002/ejoc.201501552
出版狀態	已發佈 - 2016 2月 1

ASJC Scopus subject areas

物理與理論化學
有機化學

存取文件

10.1002/ejoc.201501552

其它文件與鏈接

CCDC 1426722: Experimental Crystal Structure Determination
Kotipalli, T. (Contributor), Kavala, V. (Contributor), Janreddy, D. (Contributor), Bandi, V. (Contributor), Kuo, C.-W. (Contributor) & Yao, C.-F. (Contributor), Unknown Publisher, 2016
DOI: 10.5517/cc1jwm9b, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/cc1jwm9b&sid=DataCite
資料集: Dataset
CCDC 1407555: Experimental Crystal Structure Determination
Kotipalli, T. (Contributor), Kavala, V. (Contributor), Janreddy, D. (Contributor), Bandi, V. (Contributor), Kuo, C.-W. (Contributor) & Yao, C.-F. (Contributor), Unknown Publisher, 2016
DOI: 10.5517/cc1j7p0g, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/cc1j7p0g&sid=DataCite
資料集: Dataset

引用此

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

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\}",

note = "Publisher Copyright: {\textcopyright} 2016 Copyright WILEY-VCH Verlag GmbH \& Co. KGaA, Weinheim.",

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doi = "10.1002/ejoc.201501552",

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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

PY - 2016/2/1

Y1 - 2016/2/1

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

UR - https://www.scopus.com/pages/publications/84959111434

UR - https://www.scopus.com/pages/publications/84959111434#tab=citedBy

U2 - 10.1002/ejoc.201501552

DO - 10.1002/ejoc.201501552

M3 - Article

AN - SCOPUS:84959111434

SN - 1434-193X

VL - 2016

SP - 1182

EP - 1193

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 6

ER -

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

摘要

ASJC Scopus subject areas

存取文件

其它文件與鏈接

指紋

資料集

CCDC 1426722: Experimental Crystal Structure Determination

CCDC 1407555: Experimental Crystal Structure Determination

引用此