Palladium-Catalyzed, Microwave-Assisted Synthesis of 3,4-Dihydro-3-oxo-2H-1,4-benzoxazines: An Improved Catalytic System and Multicomponent Process

Gaofeng Feng; Shengnan Wang; Weiting Li; Fengjiang Chen; Chenze Qi

doi:10.1055/s-0033-1338508

Synthesis, Table of Contents

Synthesis 2013; 45(19): 2711-2718
DOI: 10.1055/s-0033-1338508

paper

Palladium-Catalyzed, Microwave-Assisted Synthesis of 3,4-Dihydro-3-oxo-2H-1,4-benzoxazines: An Improved Catalytic System and Multicomponent Process

Authors

Gaofeng Feng*

Zhejiang Key Laboratory of Alternative Technologies for Fine Chemicals Process, Shaoxing University, Shaoxing 312000, P.R. of China Fax: +86(575)88345682 Email: chfeng@usx.edu.cn Email: qichenze@usx.edu.cn
Shengnan Wang

Zhejiang Key Laboratory of Alternative Technologies for Fine Chemicals Process, Shaoxing University, Shaoxing 312000, P.R. of China Fax: +86(575)88345682 Email: chfeng@usx.edu.cn Email: qichenze@usx.edu.cn
Weiting Li

Zhejiang Key Laboratory of Alternative Technologies for Fine Chemicals Process, Shaoxing University, Shaoxing 312000, P.R. of China Fax: +86(575)88345682 Email: chfeng@usx.edu.cn Email: qichenze@usx.edu.cn
Fengjiang Chen

Zhejiang Key Laboratory of Alternative Technologies for Fine Chemicals Process, Shaoxing University, Shaoxing 312000, P.R. of China Fax: +86(575)88345682 Email: chfeng@usx.edu.cn Email: qichenze@usx.edu.cn
Chenze Qi*

Zhejiang Key Laboratory of Alternative Technologies for Fine Chemicals Process, Shaoxing University, Shaoxing 312000, P.R. of China Fax: +86(575)88345682 Email: chfeng@usx.edu.cn Email: qichenze@usx.edu.cn

Abstract

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Abstract

An improved palladium-catalyzed system is established for the synthesis of 3,4-dihydro-3-oxo-2H-1,4-benzoxazines from less reactive ethyl 2-(2-chlorophenoxy)alkanoates and aryl amines under controlled microwave heating, employing 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (XPhos) as the ligand. Moreover, a high-yielding, three-component reaction protocol is disclosed for the efficient one-pot synthesis of 3,4-dihydro-3-oxo-2H-1,4-benzoxazines from 2-halophenols, ethyl 2-bromoalkanoates, and aryl amines. Microwave heating at high temperature is necessary to achieve high yields with 2-chlorophenol. A wide range of substrates is tolerated affording the desired products in good to excellent yields.

Key words

multicomponent reactions - microwave irradiation - palladium-catalyzed - 3,4-dihydro-3-oxo-2H-1,4-benzoxazines - cascade process

Full Text

References

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Supplementary Material

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