One pot, three component synthesis of fluoro and trifluoromethyl substituted unsymmetrical dihydropyrazine fused acridine-3-carboxamide using renewable 2-MeTHF solvent and their DFT studies

Abstract

Six novel unsymmetrical trisubstituted urea derivatives were synthesized, characterised and their DFT studies were reported in this present work. 1,1′-carbonyldiimidazole (CDI) was used to generate carbonyl functional group of unsymmetrical urea by employing non-hazardous, renewable 2-MeTHF solvent. Excellent yields of unsymmetrical urea (90-95%) and higher purities of the products (>97%) were achieved under slow addition of a solution of 1.5 equivalent of CDI in 2-MeTHF to a pre-dissolved solution of 1.0 equivalent of fluoro or trifluoromethyl substituents containing aniline and 1.0 equivalent of dihydropyrazine fused acridine in 2-MeTHF at room temperature. Column chromatographic purification is not required in this methodology. DFT studies were carried for all six novel products.