Magnetic Nano-Supported p-Toluenesulfonic Acid Catalyzed Synthesis of Fused Polycyclic 1,5-Benzoxazepines via Domino Reactions

  • Shuo Li ,
  • Mingliang Wang ,
  • Laiyun Zhou ,
  • Lanzhi Wang
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  • Key Laboratory of Organic Functional Molecules of Hebei Province, College of Chemistry & Materials Science, Hebei Normal University, Shijiazhuang 050024

Received date: 2023-04-04

  Revised date: 2023-05-29

  Online published: 2023-06-26

Supported by

National Natural Science Foundation of China(21776060)

Abstract

1,5-Benzoxazepine is an important active substance found in the development of new drugs. It has the properties of anticonvulsant, anti-tumor and improving cerebral ischemia. In this work, novel, efficient and green three-component domino reactions were developed, which used substituted o-aminophenol, β-cyclic diketones and active carbonyl compounds as raw materials, self-made magnetic nano-supported p-toluenesulfonic acid (CoFe2O4@SiO2-PTSA) as catalyst, anhydrous ethanol as solvent, at room temperature. 37 fused 1,5-benzoxazepines with diverse structures were synthesized in one pot, and the mechanism of catalytic domino synthesis was proposed. This method abandons the traditional strong base dehalogenation hydrogen coupling method of aromatic halides, and has the advantages of novel synthesis method, mild reaction conditions, green reaction process, high efficiency, short time, and recyclable magnetic nanocatalyst, which provides a methodological reference for the effective synthesis of such compounds.

Cite this article

Shuo Li , Mingliang Wang , Laiyun Zhou , Lanzhi Wang . Magnetic Nano-Supported p-Toluenesulfonic Acid Catalyzed Synthesis of Fused Polycyclic 1,5-Benzoxazepines via Domino Reactions[J]. Chinese Journal of Organic Chemistry, 2023 , 43(11) : 3977 -3988 . DOI: 10.6023/cjoc202304002

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