C. Jolivet et al., SYNTHESIS AND BEHAVIOR OF FURO[2,3,4-K,L]ACRIDINES AND FURO[2,3,4-K,L]PYRANO[3,2-H]ACRIDINES, Heterocycles, 43(3), 1996, pp. 641-651
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. A
midification of this ester function with N,N-dimethylaminoalkylamines
allowed us to prepare watersoluble furo[2,3,4-k,l]pyrano[3,2-h]acridin
e and furo[2,3,4-k,I]acridine derivatives. In the course of attempts t
o saponify the ester function under aqueous sodium hydroxide basic con
ditions and to reduce it upon aluminium hydride, an abnormal ring open
ing reaction of the ethoxycarbonylated furan was ascertained.