Chemoselective reaction of 1-<i>p</i>-acetanilido-3-acetyl-5-hydroxy-2-methylindole towards methyl chloroacetate :Synthesis and antiinflammatory activity of some new 5- pyrrolyl/oxadiazolyl/triazolyl/quinazolinylmethoxyindole derivatives

Abstract

1-<i>p</i>-Acetanilido-3-acetyl-5-hydroxy-2-methylindole when treated with CH₃I and K₂CO₃ in refluxing dry acetone produces N,O-methylated 1-<i>p</i>-N-methylacetanilido-3-acetyl-5-methoxy-2-methylindole but when it is reacted with methyl chloroacetate under similar reaction conditions yields only O-alkylated 1<i>-p-</i>acetanilido-3-acetyl-5-methoxycarbonylmethoxy-2-methylindole. This indole ester on treatment with hydrazine hydrate in refluxing ethanol gives only the monocarbohydrazide which is reacted separately

with acetonyl acetone, triethyl orthoformate. CS₂, KOH/N₂H₄.H₂O, and 1,3-benzoxazine to secure pyrrolyl/oxadiazolyl/triazolyl and quinazolinylmethoxyindoles. Some of these new indole derivatives are screened for their antiinflammatoryactivity.