One-Pot Multicomponent Synthesis of Novel 2-Tosyloxyphenylpyrans under Green and Conventional Condition with Anti-inflammatory Activity

A mild, efficient, and environmentally green protocol for the synthesis of 2-tosyloxyphenylpyran derivatives 3, 4, 5, 6, 7, 8, 9, 10, 11 via reaction of 2-tosyloxybenzaldehyde (1) with malononitrile and some ketonic reagents in one-pot, three component reaction within few minutes under stirring in methanol in presence of ammonium hydroxide solution or ultrasonic irradiation. On the other hand, the same products 3, 4, 5, 6, 7, 8, 9, 10, 11 were obtained by traditional method, on treatment of 2-tosyloxybenzilidinemalononitrile (2) with the same ketonic reagents in refluxing ethanol in presence of TEA. 2-Tosyloxyphenylpyranopyrazoles 12 and 13 were obtained via treatment of compound 1 with malononitrile, hydrazine hydrate or phenyl hydrazine and ethyl acetoacetate, in one-pot, multicomponent reaction (MCRs). The structures of the new compounds were elucidated by elemental and spectral analyses. The newly synthesized compounds showed promising anti-inflammatory activity.