Issue 43, 2022

(3 + 2) cycloaddition of 2-alkoxynaphthalenes with azaoxyallyl cations: access to benzo[e]indolones

Abstract

A reaction between 2-alkoxynaphthalene and an in situ formed azaoxyallyl cation has been reported under ambient reaction conditions. The (3 + 2) cycloaddition reaction followed by aryl C–OMe/C–OEt bond cleavage produces a variety of benzo[e]indolone derivatives. Based on the isolated intermediate from the control experiment and previous results, a possible mechanism has been drawn. Reduction of the N–O bond of the benzo[e]indolone derivative manifests the possibility of further functionalization of the products towards biologically important heterocyclic molecules.

Graphical abstract: (3 + 2) cycloaddition of 2-alkoxynaphthalenes with azaoxyallyl cations: access to benzo[e]indolones

  • This article is part of the themed collection: New Talent

Supplementary files

Article information

Article type
Communication
Submitted
07 Leq 2022
Accepted
05 Dit 2022
First published
06 Dit 2022

Org. Biomol. Chem., 2022,20, 8400-8404

(3 + 2) cycloaddition of 2-alkoxynaphthalenes with azaoxyallyl cations: access to benzo[e]indolones

S. Biswas, S. Duari, S. Maity, A. Roy, A. M. Elsharif and S. Biswas, Org. Biomol. Chem., 2022, 20, 8400 DOI: 10.1039/D2OB01441F

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