37489-49-9Relevant academic research and scientific papers
Detailed studies of the interaction of 3-chloroaniline with O,O′-diphenylphosphorylisothiocyanate
Babashkina, Maria G.,Robeyns, Koen,Filinchuk, Yaroslav,Safin, Damir A.
, p. 1230 - 1236 (2016)
The reaction of neat 3-chloroaniline with neat SCN-P(O)(OPh)2 leads to a new N-phosphorylated thiourea, 3-ClC6H4NHC(S)NHP(O)(OPh)2 (1). The same reaction in non-dried CH2Cl2 or C6H6 leads to the salt-like compounds [3-ClC6H4NH3]+[NCS]- (2) and [3-ClC6H4NH3]+[P(O)2(OPh)2]-·0.5C6H6 (3·0.5C6H6), respectively, while using non-dried acetone yields 1-(3-chlorophenyl)-4,4,6-trimethyl-3,4-dihydropyrimidine-2(1H)-thione (4). Dissolution of 1 in non-dried CH2Cl2, C6H6 or Me2CO leads to the direct formation of 2, 3·0.5C6H6 and 4, respectively. It was established that thione 4 is most likely formed through the thiourea 1-assisted aldol condensation of acetone leading to mesityl oxide. In turn the latter ketone interacts with 1 followed by its hydrolysis leading to 4. Compounds 1-4 have been characterized by NMR spectroscopy and elemental analysis and their molecular structures were elucidated by X-ray diffraction. Hirshfeld surface analysis showed that the structures of both 1 and 4 are mainly characterized by H?H, H?C, H?Cl and H?S contacts as well as by H?O in the structure of 1. The enrichment ratio, derived as the decomposition of the crystal contact surface between pairs of interacting chemical species, for 1 was found, as expected for the polar contacts, which are generally hydrogen bonds, to be significantly larger than unity for the contacts of the type H?O and H?S. A much larger than unity value was found for the enrichment ratio of the C?C contacts in the structure of 1, which is due to extensive π?π stacking in the crystal packing. The enrichment ratio for 4 was found to be larger than unity for the contacts of the type H?C and, but with a lesser degree, H?Cl and H?S.
New Substituted 1-Aryl-4,4,6-Trimethyl-3,4-Dihydropyrimidine-2-(1H)Thiones; A Metal-Free and Solvent-Free Synthesis, Characterization, and Lymphoid Tyrosine Phosphatase Inhibition Studies
Khurshid, Asma,Saeed, Aamer
, p. 224 - 230 (2017/02/23)
A series of fourteen 3,4-dihydropyrimidine-2-thiones (3a–n) were synthesized by a green protocol, and their structures were characterized by spectroanalytical data. The compounds were obtained in high yields by efficient annulation of mesityl oxide (4-methylpent-3-en-2-one) with anilines in the presence of potassium thiocyanate. The reaction is essentially metal-catalyst- and solvent-free, as mesityl oxide itself is the solvent as well as the reactant. The compounds were tested for their ability to inhibit the lymphoid tyrosine phosphatase PTPN22, and 5 of the 14 compounds exhibited IC50 values in the mid-micromolar range, with the most potent hit being the compound 3d, having a methoxy substituent at the 2-position of the phenyl ring with an IC50 = 18 ± 1 μM, and second most potent compound (3c) with an IC50 value of 45 ± 3 μM, having methyl substituents at both 2- and 4-position of the phenyl ring.
Synthesis of Polynitroaryl Derivatives of 3-Aryl-1H,4H-dihydro-4,6,6-trimethyl-pyrimidine-2-thiols as Possible Fungicides
Sangal, S. K.,Kumar, Ashok,Rastogi, Pawan,Prakash, Om
, p. 596 - 599 (2007/10/02)
Fortyeight new 3-aryl-1,4-dihydro-2-polynitroarylmercapto-4,6,6-trimethylpyrimidines (1-6) have been prepared in good yields by the condensation of appropriate active chlorobenzene and pyrimidine-2-thiol (A) in the presence of anhydrous sodium acetate in
