The intramolecular reaction of acetophenone -tosylhydrazone and vinyl: Brønsted acid-promoted cationic cyclization toward polysubstituted indenes.

Chem Commun (Camb)

School of Petrochemical Engineering, and Jiangsu Key Laboratory of Advanced Catalytic Materials & Technology, Changzhou University, Changzhou 213164, P. R. China and Institute of New Materials & Industry Technology, College of Chemistry & Materials Engineering, Wenzhou University, Wenzhou 325035, P. R. China.

Published: February 2021

In the presence of TsNHNH2, a Brønsted acid-promoted intramolecular cyclization of o-(1-arylvinyl) acetophenone derivatives was developed, leading to polysubstituted indenes with complexity and diversity in moderate to excellent yields. In sharp contrast with either the radical or carbene involved cyclization of aldehydic N-tosylhydrazone with vinyl, a cationic cyclization pathway was involved, where N-tosylhydrazone served as an electrophile and alkylation reagent during this transformation.

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Source
http://dx.doi.org/10.1039/d0cc07966aDOI Listing

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