Reaction of Amidrazones with 2,3-Diphenylcyclopropenone: Synthesis of 3-(aryl)-2,5,6-Triphenylpyrimidin-4(3H)-ones

Abstract

Amidrazones react with 2,3-diphenylcyclopropenone to give 3-aryl-2,5,6-triphenylpyrimidin-4(3H)-one derivatives in good yields. The synthesised compounds were characterised by spectroscopic tools and their structures confirmed by X-ray crystallography. A rational mechanism of formation of the products is presented.

Heterocycles from cyclopropenones

“…111 Aly et al in 2016, successfully synthesized pyrimidines 117af in 67-87% yield, via the reaction between 116a-f and 1b in EtOH and Et 3 N (Scheme 70). 112 The proposed reaction mechanism is illustrated in Scheme 71; the carbonyl group of cyclopropenone was attacked by the hydrazine nitrogen atom yielding intermediate B, following which an amidine-like reaction of N-3 to carbonyl may occur to obtain salt C. Nucleophilic addition to positively charged Mohan and Jose, in 2017, have reported that reaction between (E)-disubstituted diazene-1,2-dicarboxylates 120a-j and diarylcyclopropenone 1 in DCM at room temperature. The reaction was catalyzed by PPh 3 to afford substituted 1,3-oxazin-6-one 121a-j in 50-70% yield (Scheme 73).…”

“…Aly et al in 2016, successfully synthesized pyrimidines 117a–f in 67–87% yield, via the reaction between 116a–f and 1b in EtOH and Et 3 N (Scheme 70). 112…”

“…Nucleophilic addition to positively charged nitrogen via ring opening followed by proton transfer would afford D , and the final product 117 was obtained by losing ammonia from D (Scheme 71). 112…”

Novel quinoline/thiazinan-4-one hybrids; design, synthesis, and molecular docking studies as potential anti-bacterial candidates against MRSA

“…25 The reaction of alkenylidenehydrazine-carbothioamides with cyclopropenone, as well as the presence of nucleophilic sites like azomethine carbon and sulfur atoms, resulted in 3,5-disubstituted 1,3,4-thiadiazolyl-2,3-diphenylpropenones. 26 The reaction of cyclopropenone with various aldehyde 4-phenyl thiosemicarbazones in acetic acid afforded pyrrolo[2,1- b ]oxadiazoles through [2 + 3]cycloaddition; H 2 S was eliminated. 27 Moreover, 2,4-disubstituted thiosemicarbazides reacted with cyclopropenone to afford the corresponding pyridazines.…”

Selectivity of amidrazones towards activated nitriles – synthesis of new pyrazoles and NMR investigation

“…[1][2][3][4][5] Recently, we have reported that amidrazones reacted with 2,3-diphenylcyclopropenone via extrusion of ammonia to give 3-(aryl)-2,5,6-triphenylpyrimidin-4(3H)-ones. 6 For a very long time, the usefulness and great therapeutic value of the pyrazole nucleus have been recognized and the activities of this nucleus have been evaluated. 7 Phenazone (antipyrine), a pyrazolin-5-one, was one of the first synthetic drugs.…”