AMINOMETHYL DERIVATIVES OF NAPHTHO[1,2-B]FURAN - SYNTHESIS

Aminomethyl derivatives of naphtho [1,2-b] furan were synthesized. The respective 4-aminomethyl derivatives were produced from 2-methyl-3-ethoxycarbonyl-5-hydroxynaphtho [1,2-b] furan by the Mannich reaction; oxidation gave rise to a 4,5-dioxy[1,2-b] furan derivative (I); acetylation yielded an O-acetyl derivative (II), and chlorination produced 4-chloronaphthofuran (III) that was converted to a more stable O-acetyl derivative (IV). The respective 2-aminomethyl derivatives were synthesized from I, II, IV naphthofurans by a series of consecutive conversions involving stages of bromination and replacement of bromine by an amine residue. The synthesized aminomethyl derivatives were tested for biological activity and were found to show a weak antimicrobial activity.