A New Facile, High Yielding and Efficient Protocol for the Synthesis of Novel 4-Phenylsulfonamido-6-Aryl-2-Phenylpyrimidine-5-Carbonitrile Derivatives

GRAPHICAL ABSTRACT

Abstract

A series of novel 4-phenylsulfonamido-6-aryl-2-phenylpyrimidine-5-carbonitrile derivatives have been synthesized through a two-step process. This protocol includes a facile surfactant-mediated methodology for the synthesis of 4-amino-6-aryl-2-phenylpyrimidine-5-carbonitrile derivatives through a one-pot, three-component reaction in the presence of a catalytic amount of cetyltrimethylammonium bromide in water. No additional organic solvents and oxidants were used. The pyrimidine-5-carbonitrile products were then subjected to a direct sulfonylation of 4-amino group to 4-phenylsulfonamide-6-aryl-2-phenylpyrimidine-5-carbonitrile derivatives in the presence of sodium hydride in tetrahydrofuran solution. These new structures were confirmed by ¹H- and ¹³CNMR spectroscopy as well as mass spectrometry and elemental analyses.

Keywords:

• Heterocycles
• sulfonylation
• green chemistry
• surfactants
• 4-sulfonamidopyrimidine-5-carbonitrile

ACKNOWLEDGMENTS

The authors gratefully acknowledge Dr. Khosrow Jadidi from Shahid Beheshti University, G. C. Tehran, Iran for his helpful consultations and sincere guidance.