Synthesis and Reactions of 2-[(methylsulfanyl) (phenylamino) and 2-[(methylsulfanyl)(N-methylphenylamino) methylidene]-1,3-diphenyl- propane-1,3-dione

Abstract

The objective of this research is to investigate the potential applications of 1,3-diphenylpropane-1,3-dione (1) in the synthesis of novel heterocyclic compounds. This can be achieved by combining 1,3-diphenylpropane-1,3-dione (1) with phenyl isothiocyanate in dimethylformamide while potassium hydroxide is present. An equimolar quantity of methyl iodide is subsequently incorporated, yielding 2-[(methylsulfanyl)(phenylamino)methylidene]-1,3-diphenylpropane-1,3-dione (3). Contrarily, the addition of two equimolar amounts of methyl iodide resulted in the formation of 2-[(methylsulfanyl)(N-methylphenylamino)methylidene]-1,3-diphenylpropane-1,3-dione (4), which used as starting materials. When chemical compound 3 was combined with hydrazine and phenylhydrazine in refluxing ethanol, it resulted in (phenylamino)-1H-pyrazole derivatives 27a,b. Chemical 3 combines with 3-phenyl-5-amino-(1H)-pyrazole (6) and 2-aminobenzimidazole (7), aminopyrazole derivatives 10a-c, to form, pyrazolo[1,5-a]pyrimidine derivative 8 and pyrimido[1,2-a]benzimidazole derivative 9, compounds 12a-c, respectively.  Moreover, component 4 can be treated with urea, thiourea, 2-aminopyridine (15) and 2-aminobenzothiazole (16) resulting in the corresponding 2-hydroxy-6-phenylpyrimidine derivative 13, and 4-phenyl-2-thioxopyrimidine derivative 14, compounds 17 and 18. Additionally, ingredient 1 produces pyridine-3-carbonitrile equivalents 22a-c through its interaction with arylidenemalononitriles 19a-c.