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Lewis Acid-Mediated Efficient Synthesis of 4H-1,3-benzo-xazines and Their Derivatives 4,5-dihydro-1,3-benzo-xazepines

Author(s):

An Junkai, Liu Jikun, Shi Ying, Zhu Weiwei, Guo Guoying, Jiang Xianxing, Xue Jijun* and Zhang Hongrui   Pages 1 - 11 ( 11 )

Abstract:


Compounds containing 4H-1,3-benzo-xazine core usually possess characteristic features and have been applied in the fields of organic synthesis, pharmaceutical research, materials science and bioscience. Here we reported a convenient and direct access to 4H-1,3-benzo-xazines and their derivatives through intramolecular cyclization of olefinic amides or ureas with good to excellent yields in the presence of TMSOTf. The properties (mild conditions, metal or additives-free, wide substrate scope and functional group tolerance) of the process made it a promising strategy to synthesis of various benzoxazines and their derivatives.

Keywords:

Olefinic amides, intramolecular cyclization, TMSOTf, benzoxazine, mild conditions, metal-free.

Affiliation:

State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, Gansu, State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, Gansu, State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, Gansu, School of Pharmaceutical Sciences, Sun Yat-Sen University Guangzhou, 510006, School of Pharmaceutical Sciences, Sun Yat-Sen University Guangzhou, 510006, School of Pharmaceutical Sciences, Sun Yat-Sen University Guangzhou, 510006, State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, Gansu, State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, Gansu



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