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Paper | Regular issue | Vol 43, No. 3, 1996, pp.641-651
Published online, 1st January, 1970
DOI: 10.3987/COM-95-7342
Synthesis and Behaviour of Furo[2,3,4-k,l]acridines and Furo[2,3,4-k,l]pyrano[3,2-h]acridines

Catherine Jolivet, Christian Rivalle, Alain Croisy, and Emile Bisagni*

*URA 1387 CNRS, Institut Curie, Section de Recherche, Bat 110-112, Centre Universitaire 91405 Orsay, France

Abstract

From noracronycine and 1-hydroxy-3-methoxy-10-methylacridone, a [2,3,4-k,l] fused furan ring bearing an ethoxycarbonyl group was built up. Amidification of this ester function with N,N-dimethylaminoalkylamines allowed us to prepare watersoluble furo[2,3,4-k,l]pyrano[3,2-h]acridine and furo[2,3,4-k,l]acridine derivatives. In the course of attempts to saponify the ester function under aqueous sodium hydroxide basic conditions and to reduce it upon aluminium hydride, an abnormal ring opening reaction of the ethoxycarbonylated furan was ascertained.