35600-34-1Relevant articles and documents
Mechanistic investigation and DFT calculation of the new reaction between S-methylisothiosemicarbazide and methyl acetoacetate
Markovic, Violeta,Markovic, Svetlana,Janicijevic, Ana,Rodic, Marko V.,Leovac, Vukadin M.,Todorovic, Nina,Trifunovic, Snezana,Joksovic, Milan D.
, p. 2127 - 2136 (2013)
A study on the synthesis and mechanistical aspects of formation of 3-methyl-5-oxo-3-pyrazolin-1-carboxamide (MOPC) starting from S-methylisothiosemicarbazide hydrogen iodide and methyl acetoacetate was performed. In the alkaline aqueous solution, the intermediate methyl acetoacetate S-methylisothiosemicarbazone undergoes substitution of CH 3S- anion by hydroxide anion, cyclization, carbanion formation, and elimination of methanol, thus yielding corresponding Na-enolate salt of pyrazol-5-one derivative. The structure of the compound obtained after protonation of the formed enolate salt was determined by means of spectroscopic techniques and single-crystal X-ray diffraction analysis. The mechanism of conversion of methyl acetoacetate S-methylisothiosemicarbazone into MOPC was investigated by means of the B3LYP functional, and it was found that the reaction is thermodynamically controlled.
Selenium-containing heterocycles from isoselenocyanates: Synthesis of 5-amino-2,4-dihydro-3H-1,2,4-triazole-3-selones
Sommen, Geoffroy L.,Linden, Anthony,Heimgartner, Heinz
, p. 641 - 651 (2007)
The reaction of S-methylisothiosemicarbazide hydroiodide (=S-methyl hydrazinecarboximido-thioate hydroiodide; 1), prepared from thiosemicarbazide by treatment with MeI in EtOH, and aryl isoselenocyanates 5 in CH 2Cl2 affords 3H-1,2,4-triazole-3-selone derivatives 7 in good yield (Scheme 2, Table 10). During attempted crystallization, these products undergo an oxidative dimerization to give the corresponding bis(4H-1,2,4-triazol-3-yl) diselenides 11 (Scheme 3). The structure of 11a was established by X-ray crystallography.
Synthesis and antioxidant activities of new nickel(II) complexes derived from 4-benzy-loxysalicylidene-S-methyl/propyl thiosemicarbazones
Eglence-Bakir, Songül
, p. 835 - 844 (2021/07/26)
Six nickel(II) complexes of the N2O2chelating thiosemicarbazones were synthesized using N1-4-benzyloxysalicylidene-S-methyl/propyl thiosemicarbazone and methoxy-substitute-salicylaldehydes in the presence of Ni(II) ion by template reaction. The structures of thiosemicarbazones and nickel(II) complexes were characterized by elemental analysis, UV-Vis, IR, and 1H-NMR spectroscopies. The structure of the N1-4-benzyloxysalicylidene-S-propyl thiosemicarbazone (2) was determined by X-ray single-crystal diffraction method. The total antioxidant capacities of synthesized compounds were evaluated by using cupric reducing antioxidant capacity (CUPRAC) method. The thiosemicarbazones exhibited more potent antioxidant capacity than Ni(II) complexes. Trolox equivalent antioxidant capacity (TEAC) of 1c was found highest in tested nickel(II) complexes. In addition, antioxidant activities of tested compounds were evaluated by using the hydroxyl radical, DPPH radical, and ABTS radical scavenging abilities of these compounds.
New M(II) (M=Mn, Co, Ni, Cu, Zn, Pd) coordinative compounds with 2-formylpyridine S-methyl-isothiosemicarbazide
Danac, Ramona,Pui, Aurel,Corja, Ion,Amarandi, Roxana-Maria,Ciobanu, Catalina Ionica,Apostu, Mircea-Odin,Palamarciuc, Oleg
, (2020/02/03)
The synthesis and structure of the new organic proligand 2-formylpyridine S-methyl-isothiosemicarbazone in a bi-protonated form (HL.2HCl) and its coordination compounds with Mn(II) - [Mn(HL)·Cl2], Co(III) - [CoL2]·ClO4, Ni(II) - [Ni(HL)2]·2ClO4, Cu(II) - [Cu(HL)Cl2]·(H2O), Zn(II) - [Zn(HL)2]·2(ClO4)·(H2O) and Pd(II) - [Pd(HL)·Cl]·Cl are reported. According to the X-ray investigation, the ligand has the molecular form of HL in the case of Mn(II), Cu(II), Zn(II) and Pd(II) compounds, and the deprotonated form L? in case of the Co(III) complex. The ligand coordinates to the metal ions via a N,N,N set of donors atoms in case of Zn(II), Cu(II) and Co(III). For Mn(II), the ligand coordinates via N,N donor atoms, whereas in the case of Pd(II) metal ions, the coordination sphere is N,N,S. This latter coordination mode (via S(CH3)) has been previously reported in case of salicylaldehyde S-alkyl-isothiosemicarbazones.