Boron Trifluoride Diethyl Etherate Catalyzed Synthesis of 1-(Carbamoylmethyl)-2-Aryl/Alkyl-3,1-Benzoxazines

doi:10.11944/j.issn.1000-0518.2018.10.170352

Chinese Journal of Applied Chemistry ›› 2018, Vol. 35 ›› Issue (10): 1190-1200.DOI: 10.11944/j.issn.1000-0518.2018.10.170352

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Boron Trifluoride Diethyl Etherate Catalyzed Synthesis of 1-(Carbamoylmethyl)-2-Aryl/Alkyl-3,1-Benzoxazines

TANG Zilong^a^b^*(),WANG Lian^a^b,TAN Jingzhao^a^b,YAO Yuan^a^b,PENG Lifeng^a

^aKey Laboratory of Theoretical Organic Chemistry and Functional Molecule,Ministry of Education,Hu'nan University of Science and Technology,Xiangtan,Hu'nan 411201,China
^bSchool of Chemistry and Chemical Engineering,Hu'nan University of Science and Technology,Xiangtan,Hu'nan 411201,China

Received:2017-09-26 Accepted:2017-11-24 Published:2018-10-01 Online:2018-10-09
Contact: TANG Zilong
Supported by:
Supported by the National Natural Science Foundation of China(No.201372070), the Subproject of National Key Technology R&D Program(No.2011BAE06B01), the Scientific Research Fund of Hunan Provincial Education Department (No.17A066), the Open Project of Key Laboratory of Theoretical Organic Chemistry and Fuctional Molecules of Ministry of Education(No.LKF1506)

Abstract

Abstract:

Boron trifluoride diethyl etherate(BF₃·OEt₂)catalyzed reaction of 2-(N-substituted amino)benzyl alcohol with aldehyde was studied, and resulted a new method for the preparation of substituted 3,1-benzoxazine. By this method, a series of novel 1-(carbamoylmethyl)-2-aryl/alkyl-3,1-benzoxazines was prepared. It was found that BF₃·OEt₂ was a more general catalyst for these reactions than chlorotrimethylsilane and SnCl₄ for the reaction and the reason causing this difference was discussed.

Key words: nitrogen heterocycles, substituted 3,1-benzoxazines, synthesis, boron trifluoride diethyl etherate, catalyst

TANG Zilong,WANG Lian,TAN Jingzhao,YAO Yuan,PENG Lifeng. Boron Trifluoride Diethyl Etherate Catalyzed Synthesis of 1-(Carbamoylmethyl)-2-Aryl/Alkyl-3,1-Benzoxazines[J]. Chinese Journal of Applied Chemistry, 2018, 35(10): 1190-1200.

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Boron Trifluoride Diethyl Etherate Catalyzed Synthesis of 1-(Carbamoylmethyl)-2-Aryl/Alkyl-3,1-Benzoxazines

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