Synthesis of novel naphtho[2,1<i>-b</i>]furopyrimidine derivatives

Abstract

2-Acyl-3-aminonaphtho[2,1-<i>b</i>]furans <b>2a-c</b> are converted into corresponding oximes <b>3a-c</b> ,which on reaction with chloroacetyl chloride in the presence of triethylamine yield 2-chloromethyl-4-alkyl/arylnaphtho[2, 1<i>-b</i>]furo[3,2-<i>d</i>]pyrimidine-3-oxides <b>4a-c.</b> Acylation of compounds <b>2a-c</b> furnish 2-acyl-3-acylamidonaphtho[2,1-<i>b</i>]furans <b>5a-f</b>, which undergo

ring closure, on reacting with hydrazine hydrate and produce 2-alkyl/aryl-3,4-dihydro-3-amino-4-hydroxy-4-alkyl/aryl-naphtho[2,l–<i>b</i>]furo[3,2-<i>d</i>]pyrimidines <b>6a-f.</b> Compounds <b>6a-f</b> when refluxed with formic acid undergo ring opening and rearrangement simultaneously to give 2-acyl-3-(3'-alkyl/aryl-1',2',4'-triazol-4'-yl)naphtho[2,1<i>-b</i>]furans <b>7a-f</b>. The compounds synthesized have been screened for antimicrobial anthelmintic and anti-inflammatory activity.