(3 + 2) cycloaddition of 2-alkoxynaphthalenes with azaoxyallyl cations: access to benzo[e]indolones
Subrata Biswas1, Surajit Duari1, Srabani Maity1
1Dept. of Chemistry, University of Calcutta, 92, A. P. C. Road, Kolkata-700 009, West Bengal, India. sbchem@caluniv.ac.in.
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.
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