Copper–Catalyzed Multicomponent Reactions for Efficient Synthesis of Diverse Spirotetrahydrocarbazoles

  1. Shao-Cong Zhan,
  2. Ren-Jie Fang,
  3. Jing Sun and
  4. Chao-Guo YanORCID Logo

Submitting author affiliation: Yangzhou University, Yangzhou, China

Beilstein Arch. 2022, 202235. https://doi.org/10.3762/bxiv.2022.35.v1

Published 12 May 2022

  • Preprint

Abstract

In the presence of copper sulfate, the three or four-component reactions of 2-methylindole, aromatic aldehydes and various cyclic dienophiles in refluxing toluene afforded diverse spirotetrahydrocarbazoles. This reaction is a important development of Levy reaction by using 2-methylindole to replacing ethyl indole-2-acetate and successfully provided facile access to important polysubstituted spiro[carbazole-3,3'-indolines], spiro[carbazole-2,3'-indolines], spiro[carbazole-3,5'-pyrimidines] and spiro[carbazole-3,1'-cycloalkanes] in satisfactory yields and with high diastereoselectivity.

Keywords: Tetrahydrocarbazole; indole;  spirooxindole; indolo-2,3-quinodimethane; Diels-Alder reaction;  Levy reaction. .

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Zhan, S.-C.; Fang, R.-J.; Sun, J.; Yan, C.-G. Beilstein Arch. 2022, 202235. doi:10.3762/bxiv.2022.35.v1

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