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Paper | Regular issue | Vol 38, No. 1, 1994, pp.103-111
Published online, 1st January, 1970
DOI: 10.3987/COM-93-6520
Synthesis of 2-Substituted 2,3-Dihydro-9-phenyl-1H-pyrrolo[3,4-b]quinolin-3-ones as Potential Peripheral Benzodiazepine-Receptor Ligands

Maurizio Anzini, Andrea Cappelli,* and Salvatore Vomero

*Dipartimento Farmaco Chimico Technlogico, Università degli Studi di Siena, Banchi di Sotto, 55 - 53100 Siena, Italy


Two synthetic routes to the achievement of the title compounds are described. 2-Chloromethyl-3-ethoxycarbonyl-4-phenylquinoline (4) was transformed into the corresponding lacton (5) which in two setps was converted into its isomeric lacton (7). Aminolysis of 7 gave γ-hydroxyamide (8) which was in turn transformed into γ-chloroamide (9). Cyclization of 9 with sodium hydride in presence of oxygen led to the oxidized compound (10), while by carrying out the cyclization reaction under inert atomosphere, 2-benzyl-2,3-dihydro-9-phenyl-1H-pyrrolo[3,4-b]quinolin-3-one (3a) was obtained. Autoxidation of anion at 1-position of compound (3a) was considered to account for these results and a mechanistical interpretation was given. A simplier and more versatile route to obtain the title compounds was also developed.