Studies on Heterocyclic Compounds. XLIV. Bromination of 4-Methylfuro [2, 3-b] quinoline-Synthesis of Its Derivatives

Abstract

Bromination of 4-methylfuro [2, 3-b] quinoline (I) with bromine in carbon tetrachloride afforded 2, 3-dibromo-4-methyl-2, 3-dihydrofuro [2, 3-b] quinoline (II). Dehydrobromination of II yielded two isomeric compounds, 3-bromo-4-methylfuro [2, 3-b] quinoline (III) and 2-bromo-4-methylfuro [2, 3-b] quinoline (IV). On the other hand, treatment of I with N-bromosuccinimide in carbon tetrachloride gave 4-bromomethylfuro [2, 3-b] quinoline (V). The reaction of V with NaCN in DMF gave an unexpected dimeric cyano compound (VI), whereas the reaction with aliphatic secondary amines (diethylamine, piperidine, morphorine, or pyrrolidine) in benzene gave the expected tert-amino compounds (VIIa-VIId).