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Paper | Regular issue | Vol 24, No. 11, 1986, pp.3181-3186
Published online, 1st January, 1970
DOI: 10.3987/R-1986-11-3181
Synthesis of 2H-Pyrazolo[3,4-c]quinoline Derivatives by One Pot Rearrangement of Phenylhydrazones of 3-Acylindoles

Giuseppe Cusmano,* Gabriella Macaluso, Nicolò Vivona, and Michele Ruccia

*Instituto de Chimica Organica, Facolta de Scienze, Università digli Studi di Palermo, 20 via Archirafi, 90123 Palermo, Italy

Abstract

The phenylhydrazones 4a-g of 3-acylindoles led to the 2-phenyl-2H-pyrazolo[3,4-c]quinoline derivatives 9a-e and 10a-b. The reaction mechanism proposed involves an acid catalyzed 6Π heteroelectrocyclic reaction and a ring opening to the pyrazole derivatives 8 followed by a spontaneous ring closure of the latter compounds.