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Paper | Regular issue | Vol 45, No. 7, 1997, pp.1337-1343
Published online, 1st January, 1970
DOI: 10.3987/COM-97-7815
Unexpected Rearrangement of 2-Carboxymethyleneindan-1-one Arylhydrazones to Spiro[indan-2,4'-quinoline] Keto Lactams

Fausta Palluotto, Giuliano Delle Monache, Giovanni Casini, and Francesco Campagna*

*Dipartimento di Farmaco Chimico, Università degli Studi di Bari, Via E. Orabona 4, 70125 Bari, Italy

Abstract

The reaction of 1-keto-2-indanylacetic acid (3) with substituted phenylhydrazine hydrochlorides (4) yielded the spiro[indan-2,4’-quinoline] keto lactams (6). The structures of compounds (6) were assigned on the basis of 1H- and 13C-NMR analyses. A possible reaction mechanism is proposed.