Facile and efficient syntheses of 4‐(1H‐pyrrol‐1‐yl)‐coumarins and 6‐(1H‐pyrrol‐1‐yl)‐coumarins from the corresponding aminocoumarins are reported. The transformations were optimized and their corresponding scope and limitations were assessed. Selected (1H‐pyrrol‐1‐yl)‐coumarins were further subjected to a mild thiocyanation, undergoing selective functionalization on the pyrrole nucleus. A set of 10 differently substituted compounds was submitted to activity testing against various fungal strains. It was found that the introduction of a SCN moiety increased the antifungal activity, turning some compounds into fungicidal agents, to the point that one of the thiocyanato derivatives displayed an antifungal profile comparable to those of fluconazole and nystatin.

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A simple and robust coupling protocol is reported to provide the previously unknown indole derivatives carrying vinylsulfide motifs attached to C−3 of the heterocycle. The developed strategy involved a Wittig‐Horner reaction with different phosphinoxide derivatives. The reaction conditions were optimized and its scope and limitations were assessed. The target compounds, including 3‐arylvinylsulfides as well as symmetric and dissymmetric bis‐vinylsulfides, were obtained in a straightforward way, as mixtures of geometric isomers, in good to excellent yields.

A facile, simple and metal-free protocol for the 4-sulfanylation of 3-bromocoumarins was developed. It involves a thia-Michael addition and a dehydrobromination under DABCO assistance.

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