1442 One-Pot Multicomponent Synthesis of Novel 2-Tosyloxyphenylpyrans
under Green and Conventional Condition with Anti-inflammatory Activity
Vol 54
,
a
,
a
*
,
b
and
a
a
Department of Organic Chemistry, Faculty of Science, Sohag University, Sohag 82524, Egypt
b
Department of Pharmaceutical Medicinal Chemistry, Faculty of Pharmacy, Sohag University, Egypt
*E-mail: elssan@yahoo.com
Additional Supporting Information may be found in the online version of this article.
Received April 16, 2016
DOI 10.1002/jhet.2730
Published online 19 July 2016 in Wiley Online Library (wileyonlinelibrary.com).
A mild, efficient, and environmentally green protocol for the synthesis of 2-tosyloxyphenylpyran
derivatives 3-11 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 3-11 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 ele-
mental and spectral analyses. The newly synthesized compounds showed promising anti-inflammatory activity