Efficient synthesis of polyfunctionalized carbazoles and pyrrolo[3,4-c]carbazoles via domino Diels-Alder reaction

  1. Ren-Jie Fang,
  2. Chen Yan,
  3. Jing Sun,
  4. Ying Han and
  5. Chao-Guo YanORCID Logo

Submitting author affiliation: Yangzhou University, Yangzhou, China

Beilstein Arch. 2021, 202153. https://doi.org/10.3762/bxiv.2021.53.v1

Published 28 Jul 2021

  • Preprint

Abstract

p-TsOH catalyzed Diels-Alder reaction of 3-(indol-3-yl)maleimides with chalcone in toluene at 60 oC afforded two diastereoisomers of tetrahydropyrrolo[3,4-c]carbazoles, which can be dehydrogenated by DDQ oxidation in acetonitrile at room temperature to give the aromatized pyrrolo[3,4-c]carbazoles in high yields. On the other hand, the one-pot reaction of 3-(indol-3-yl)-1,3-diphenylpropan-1-ones with chalcones in acetonitrile in the presence of p-TsOH and DDQ resulted in polyfunctionalized carbazoles in satisfactory yields. The reaction mechanism included DDQ oxidative dehydrogenation of 3-(indol-3-yl)-1,3-diphenylpropan-1-ones to the corresponding 3-vinylindoles, its acid-catalyzed Diels-Alder reaction and sequential aromatization process.

Keywords: maleimide; chalcone; carbazole; 3-vinylindole; pyrrolo[3,4-c]carbazole; Diels-Alder reaction.

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Fang, R.-J.; Yan, C.; Sun, J.; Han, Y.; Yan, C.-G. Beilstein Arch. 2021, 202153. doi:10.3762/bxiv.2021.53.v1

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