Unusual Reactivity of 2,3-diphenylcyclopropenone towards N-imidoylthioureas; Facile Synthesis of 3-aryl-2,5,6-triphenylpyrimidin-4(3H)-one (PART III)

Abstract

2,3-Diphenylcyclopropenone (1) reacts with N-imidoylthioureas 2a–e to form the pyrimidin-4(3 H)-ones 5a–e. The reaction mechanism can be described as due to stepwise addition accompanied by elimination of phenyl isothiocyanate.

Synthesis, characterization and urease inhibition, in vitro anticancer and antileishmanial studies of Ni(II) complexes with N,N,N′-trisubstituted thioureas

“…The 13 C NMR data revealed that all the signals, due to the unique carbons present in ligands, thioureas (1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12) and the complexes (1a-12a), are in good agreement with the proposed structures. The aromatic carbon resonances of the thioureas were assigned on the basis of signal intensities and then were compared with the reported values [8][9][10][11].…”

“…Synthesis and spectroscopic studies (1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12) showed that the NH hydrogen resonates considerably downfield from other resonances in the spectra. The proton chemical shifts were found in range 8.17-8.80 ppm for NH and aromatic protons mostly appeared downfield near 6.31-8.42 ppm as multiplets.…”

“…Crystals suitable for X-ray diffraction measurements were obtained by slow evaporation of methanol/chloroform (1:1) solution of the complexes. The 1 H and 13 C NMR, FT-IR, the elemental analyses, melting point data for the ligands (1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12) and complexes (1a-12a) are as follows:…”

“…LC-MS was recorded in CH 3 CN solvent at ambient temperature on an Agilent 6310 ion trap instrument. Synthesis of N,N,N′-trisubstituted thioureas (1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12) The syntheses of N,N,N′-trisubstituted thiourea ligands were carried out according to the reported methodology [8][9][10][11]. To a solution of an appropriate acyl isothiocyanate (20 mmol) in acetone (30 mL) was added dropwise a solution of corresponding amine (20 mmol) dissolved in acetone with constant stirring.…”

“…The substituted acyl thioureas help to establish a structure-activity relationship as certain reports manifest [4,5]. These compounds have found extensive range of practices in heterocyclic chemistry, metal complexes and also exhibit a wide range of biological activities [6,7]. It has been acknowledged that the activity of the metal centres toward the target bio-molecules can be tuned through a suitable choice of ligands.…”