Synthesis of Annulated Carbazoles via FeCl3/SnCl4‑Mediated Domino Reaction of Vinyl Ketone Tethered Bromomethylindoles with Arenes and Heteroarenes

Velu Saravanan; Arasambattu K. Mohanakrishnan

doi:10.1055/a-1387-9479

Synthesis, Table of Contents

Synthesis 2021; 53(13): 2304-2318
DOI: 10.1055/a-1387-9479

paper

Synthesis of Annulated Carbazoles via FeCl₃/SnCl₄‑Mediated Domino Reaction of Vinyl Ketone Tethered Bromomethylindoles with Arenes and Heteroarenes

Velu Saravanan

,

Arasambattu K. Mohanakrishnan ∗

Abstract

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Abstract

One-pot synthesis of aryl- as well as heteroaryl-annulated carbazoles was achieved from 2/3-bromomethylindoles involving Lewis acid mediated domino reaction with arenes as well as heteroarenes via successive Friedel–Crafts intermolecular as well as intramolecular alkylations followed by elimination of acetone. Further, the bis-domino reaction of 2,5-bis(bromomethyl)pyrrole was also carried out with selected heteroarenes. Additionally, the synthesized thienocarbazoles and thienodibenzofurans were successfully utilized for a second-generation domino reaction.

Key words

carbazole - indole - pyrrole - Friedel–Crafts alkylation - Michael addition

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References

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