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Updated: Jun 29, 2025

Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes
Published on: April 1, 2013
Deconstructive annulation mediated one-pot synthesis of xanthene derivatives
Balasubramaniyam Manikandan1, Subbiah Thamotharan2, Olivier Blacque3
1Department of Chemistry, School of Chemical and Biotechnology, SASTRA Deemed University, Thanjavur-613401, Tamil Nadu, India. selva@biotech.sastra.edu.
Abstract:
Direct conversion of naphthoxazines to diverse xanthene derivatives was achieved under one-pot operation through deconstructive annulation methodology. Sequential oxidative C(sp3)-O/C(sp3)-N cleavage followed by intramolecular/intermolecular annulation reaction was carried out under aerobic reaction conditions. Mechanistic analyses performed on the substrate revealed that the C(sp3)-O bond cleavage supersedes the C(sp3)-N bond scission. The in situ generated Betti base intermediate through the C(sp3)-O cleavage was successfully isolated. Based on a molecular docking investigation, the intermolecular annulated products demonstrated good α-glucosidase inhibitory properties.
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