ONE-POT SYNTHESIS OF 1,5-BENZODIAZEPINE-2,3-DICARBOXYLATES <i>via</i> THREE-COMPONENT DOMINO REACTIONS IN THE PRESENCE OF γ-Fe2O3@SiO<sub>2</sub>/Ce(OTf)<sub>3</sub>

Authors

  • Xiaoying An Hebei Key Laboratory of Organic Functional Molecules, College of Chemistry and Materials Science, Hebei Normal University, Shijiazhuang 050024
  • Lei Gao Hebei Key Laboratory of Organic Functional Molecules, College of Chemistry and Materials Science, Hebei Normal University, Shijiazhuang 050024
  • Mingliang Wang Hebei Key Laboratory of Organic Functional Molecules, College of Chemistry and Materials Science, Hebei Normal University, Shijiazhuang 050024
  • Haitao Wu Hebei Key Laboratory of Organic Functional Molecules, College of Chemistry and Materials Science, Hebei Normal University, Shijiazhuang 050024
  • Lanzhi Wang Hebei Key Laboratory of Organic Functional Molecules, College of Chemistry and Materials Science, Hebei Normal University, Shijiazhuang 050024

DOI:

https://doi.org/10.1007/6017

Keywords:

1, 5-benzodiazepine-2, 3-dicarboxylates, 4-diazepines, γ-Fe2O3@SiO2/Ce(OTf)3, catalysis, domino reactions, multicomponent reactions

Abstract

Novel, efficient and environmentally friendly approaches have been developed for the synthesis of 1,5-benzodiazepine-2,3-dicarboxylates by
one-pot three-component domino reactions in the presence of a catalytic amount of γ-Fe2O3@SiO2/Ce(OTf)3 in EtOH at ambient temperature. A total of 32 2,5-dihydro-1H-1,5-benzodiazepine-2,3-dicarboxylates and 2-methyl-2,3-dihydro-1H-1,5-benzodiazepine-2,3-dicarboxylates with enamine or imine structure of the heterocycle, respectively, were obtained in good yields by reacting substituted 1,2-phenylenediamine, β-carbonyl esters, and ethyl glyoxylate or ethyl pyruvate. One-pot reactions were successfully realized to form one new cycle and four new bonds (one C–C, two C–N, one C=C or two C–C, one C–N, one C=N). Furthermore, plausible mechanisms for the formation of 1,5-benzodiazepine-2,3-dicarboxylates have been proposed. The salient features of this reaction include short reaction time, mild reaction conditions, moderate to excellent yields, recyclability of the catalyst, and wide substrate scope.

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Published

2021-08-26

Issue

Vol. 57 No. 7/8 (2021)

Section

Original Papers