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Report | Regular issue | Vol 23, No. 6, 1985, pp.1417-1423
Published online, 1st January, 1970
DOI: 10.3987/R-1985-06-1417
Heterocyclic Systems. V. Synthesis of 1H,4H,6H-Pyrazolo[3,4-e]pyrrolo[2,1-c][1,4]oxazepine Derivatives

Silvio Massa, Giorgio Stefancich, Marino Artico,* Federico Corelli, and Giovannni Ortenzi

*Isitituto de Chimica farmaceutica e tossicologica, Facolta di Farmacia, Università a degli Studi di Roma "La Sapienza", Piazza Aldo Moro, 5 - 00185 Roma, Italy

Abstract

The synthesis of derivatives of a new tricyclic heteroaromatic ring, 1H,4H,6H-pyrazolo[3,4-e]pyrrolo[2,1-c][1,4]oxazepine, is described. Formylation of 4-ethoxycarbonyl-1-phenyl-5-(1-pyrryl)pyrazole, prepared from 5-amino-4-ethoxycarbonyl-1-phenylpyrazole by Clauson-Kaas method, afforded 4-ethoxycarbonyl-5-(2-formyl-1-pyrryl)-1-phenylpyrazole, which was then reduced to 4-hydroxymethyl-5-(2-hydroxymethyl-1-pyrryl)-1-phenylpyrazole. Treatment of the diol with phosphorus pentoxide led to 1-phenyl-1H,4H,6H-pyrazolo[3,4-e]pyrrolo[2,1-c][1,4]oxazepine. 4-Methyl and 4-phenyl derivatives of the latter compound were also prepared.