Synthesis, characterization, and antifungal activity of novel (Z)-N-(2-cyano-3-phenylprop-2-en-1-yl)-alkyl/aryl-sulfonamides derived from a Morita–Baylis–Hillman adduct

•Nine allyl sulfonamides derived from a Morita–Baylis–Hillman adduct were prepared.•The highly stereoselective reactions yielded Z-isomers, as confirmed by X-ray diffraction.•Their activity were tested against Colletotrichum gloeosporioides.•Most of these allyl sulfonamides were more active than the primary sulfonamides.

A series of allyl sulfonamides prepared from the reaction of the Morita–Baylis–Hillman adduct 2-[hydroxy(phenyl)methyl]acrylonitrile with primary sulfonamides (RSO2NH2), where R = C6H5 (1), 4-FC6H4 (2), 4-ClC6H4 (3), 4-BrC6H4 (4), 4-NO2C6H4 (5), CH3 (6), CH3CH2 (7), CH3(CH2)3 (8), and CH3(CH2)7 (9), were characterized by IR, 1H and 13C NMR spectroscopies, mass spectrometry and elemental analyses. BLYP/6-31G* calculations suggested stereoselective reactions, resulting in the exclusive formation of the thermodynamically more stable Z-products. The Z-configuration of the products was confirmed by NOE difference spectroscopy and single crystal X-ray diffraction measurements. The allyl sulfonamides were active against Colletotrichum gloeosporioides, an important agent of anthracnose in plants.

Graphical abstractFigure optionsDownload full-size imageDownload as PowerPoint slide