Synthesis of polyfunctionally substituted pyridine-2-(1H)-thiones containing a sulfone moiety

Abstract

1-Phenyl-2-(phenylsulfonyl)ethanone (1) reacts with DMFDMA to give enamine 2, which upon treatment with cyanothioacetamide affords 3-cyano-5-benzenesulfonyl-4-phenylpyridine-2(1H)-thione (4), a compound that can also be obtained by the reaction of 1-benzenesulfonyl-1-benzoyl-2-ethoxyethene (3) with cyanothioacetamide. The reaction of 2-thiocarbamoylacetamide (8a) and N-phenyl-2-thiocarbamoylacetamide (8b) with 3-aryl-2-benzenesulfonylacrylonitrile (9a– c) affords 10a–f. The methylation of 10d–f with methyl iodide results in the formation of S-methyl derivatives (12a–c). Compound 12c can be obtained by the reaction of 13 with 9c.

Keywords:

• Dimethylformamide dimethyl acetal
• Triethylorthoformate
• Pyridine-2(1H)-thione
• 1-phenyl-2-(phenylsulfonyl)ethanone
• Dioxane

Additional information

Notes on contributors

Fathi A. Abu-Shanab

Email: [email protected]