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Paper | Regular issue | Vol 41, No. 4, 1995, pp.689-696
Published online, 1st January, 1970
DOI: 10.3987/COM-94-6955
An Efficient Synthesis of Pyrrolo[1',2':2,3]pyridazino[6,1-a]isoindoles from 1-Phthalimidopyrrole

Stephan Marchalin and Bernard Decroix

*Laboratoire de Chimie, UER des Sciences et Techniques de l'Université du Havre, 30 rue Gabriel Péri, 76600 Le Havre, France


A synthesis of pyrrolo[1’,2’:2,3]pyridazino[6,1-a]isoindole was developed. Reduction of 1-phthalimidopyrrole, followed by Wittig reaction using ethoxycarbonylmethylidenetriphenylphosphorane gave the carboxylic acid intermediate (3) which cyclized in the presence of boron trifluoride etherate to furnish the tricyclic ketone (4). Mannich reaction, Schmidt rearrangement, and reduction of the above ketone were studied.