Furan derivatives-IX : A convenient new method of arylation of furan reaction of diazoaminobenzenes with furan and isopentyl nitrite

A convenient new method for the arylation of furan with derivatives of diazoaminobenzene and isoamyl nitrite is described. Using this method the substituted 2-(X-phenyl)furan derivatives, where X is H, 4-CH₃, 4-Cl, 4-Br, 3-Cl, 3,4-diCl, 4-NO₂, 4-COOCH₃, 4-COOH, 4-Cl-3-CF₃ and 2-(3-pyridyl)furan were prepared. The reaction of methyl 4-aminobenzoate with furan and isopentyl nitrite gave (besides 2-(4-carbmethoxyphenyl)furan) 4,4′-dicarbmethoxydiazoaminobenzene, the structure of which was proved by mass spectrometry and by synthesis. This diazoaminobenzene derivative was unstable in the reaction medium and with isopentyl nitrite and furan at 30° gave 2-(4-carbmethoxyphenyl)furan. The mechanism of the reaction is discussed.