Novel Diastereoselective Synthesis and X-Ray Crystallographic Studies of (E)-2-cyano-N-(4-ethoxyphenyl)-3-methylthio-3-(substituted-amino)Acrylamides

Abstract

Three derivatives of the novel (E)-2-cyano-N-(4-ethoxyphenyl)-3-methylthio-3-(substituted-amino)acrylamides 3–5 were selectively synthesized by the one-pot reaction of 2-cyano-N-(4-ethoxyphenyl)acetamide (2) with substituted isothiocyanates and methyl iodide in DMF containing potassium hydroxide as a basic catalyst. The stereochemistry and the structures of the synthesized compounds were confirmed by single crystal X-ray diffraction, IR, ¹H-NMR, ¹³C-NMR, mass spectroscopy, and elemental analyses.

Keywords:

• Crystal structure
• cyanoacetylation
• diastereoselective
• ketene N,S-acetals
• 4-ethoxyaniline

Acknowledgments

This research project was supported by a grant from the “Research Center of the Female Scientific and Medical Colleges”, Deanship of Scientific Research, King Saud University.

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