886-60-2Relevant articles and documents
Square planar Ni(II) complexes of pyridine-4-carbonyl-hydrazine carbodithioate, 1-phenyl-3-pyridin-2-yl-isothiourea and 4-(2-methoxyphenyl) piperazine-1-carbodithioate involving N-S bonding: An approach to DFT calculation and thermal studies
Bharati,Bharti,Bharty,Maiti,Butcher,Singh
, p. 156 - 166 (2013)
Three new complexes [H2en][Ni(pchc)2] (1) (pchc = pyridine-4-carbonyl-hydrazine carbodithioate), [Ni(Hppith)2] (2) (H2ppith = 1-phenyl-3-pyridin-2-yl-isothiourea) and [Ni(mppcdt) 2] (3) {mppcdt = 4-(2-methoxyphenyl)piperazine-1-carbodithioate} have been synthesized and characterized by elemental analyses, IR and single crystal X-ray diffraction data. The ligand H2ppith and complexes [H 2en][Ni(pchc)2] (1) [Ni(Hppith)2] (2) and [Ni(mppcdt)2] (3) crystallize in monoclinic, orthorhombic, monoclinic and triclinic system with space group P21/n, Icab, C2/c and P1, respectively. The nitrogen and sulfur donor sites of the bidentate ligands chelate Ni(II) forming two five-membered CSN2M chelate rings in the complex 1, two six membered C2SN2M rings in complex 2 and the sulfur donor sites of the bidentate ligand chelate Ni(II) forming two four membered CS2M rings in complex 3. The Ni(II) complexes are diamagnetic and have distorted square planar geometry. The crystal structure of the complexes are stabilized by various types of inter and intramolecular extended hydrogen bonding providing supramolecular framework. Results obtained from quantum chemical calculations at the density functional theory level corroborate our experimental findings from IR and UV. The course of the thermal degradation of complexes 1,2 and 3 has been investigated by TG-DTA. Thermogravimetric analyses of the complexes indicate NIO/NIS as the end residue.
3-Phenyl-1-(2-pyridyl)thiourea
West, Douglas X.,Hermetet, Anne K.,Ackerman, Lily J.,Valdes-Martinez, Jesus,Hernandez-Ortega, Simon
, p. 811 - 813 (1999)
The title compound, C12H11N3S, contains an intramolecular N3 - H...Npy hydrogen bond, which stabilizes the coplanarity of the thiourea moiety and the pyridine (py) ring. The molecules form centrosymmetric hydrogen-bonded dimers, with the S atom forming bifurcated intermolecular hydrogen bonds involving the N2 - H group of the thiourea moiety and the C3 - H group of the pyridyl ring.
Synthesis and structures of two N,N′-bis(2-pyridinyl)thioureas and N-(2-pyridinyl)-N′-(benzoyl)thiourea
Kaminsky, Werner,Goldberg, Karen I.,West, Douglas X.
, p. 9 - 15 (2002)
N,N-′bis(4,6-lutidyl)thiourea, (4,6Lut)2Tu, triclinic, P-1, a = 7.4930(8), b = 8.7210(8), c = 12.6040(14) ?, α = 93.437(5), β = 94.919(5), γ = 110.246(5)°, V = 766.35(14) ?3 and Z = 2; N,N′-bis(5-picolyl)thiourea, (5Pic)2Tu, monoclinic, P21/c, a = 17.205(2), b = 4.4970(5), c = 17.425(2) ?, β = 117.763(5)°, V = 1272.6(3) ?3 and Z = 4 and N-(2-pyridyl)-N′-benzoylthiourea, PyTubenzo, monoclinic, P21/n, a = 5.345(3), b = 20.343(6), c = 11.808(2) ?, β = 90.23(3)°, V = 1290.8(1) ?3 and Z = 4. Intramolecular hydrogen bonding between N′H and the pyridyl nitrogen, intermolecular hydrogen bonding involving the thione sulfur and the NH hydrogen, and the planarity of the molecule is affected by substitution on the pyridine rings of the bis(2-pyridyl)thioureas. PyTubenzo has intramolecular hydrogen bonding to the carbonyl oxygen, intermolecular hydrogen bonding to a thione sulfur and is the least planar of the molecules under study. 1H NMR studies in CDCl3 show the NH′ hydrogen resonance considerably downfield from other resonances in the spectrum of the bis(2-pyridyl)thioureas.
Diversity-Oriented Synthesis of Thiazolidine-2-imines via Microwave-Assisted One-Pot, Telescopic Approach and Its Interaction with Biomacromolecules
Saikia, Ananya Anubhav,Rao, Ramdas Nishanth,Maiti, Barnali,Balamurali, Musuvathi Motilal,Chanda, Kaushik
, p. 630 - 640 (2020/12/15)
In this work, a one-pot, telescopic approach is described for the combinatorial library of thiazolidine-2-imines. The synthetic manipulation proceeds smoothly via the reaction of 2-aminopyridine/pyrazine/pyrimidine with substituted isothiocyanates followed by base catalyzed ring closure with 1,2-dibromoethane to obtain thiazolidine-2-imines with broad substrate scope and high functional group tolerance. The synthetic strategy merges well with the thiourea formation followed by base catalyzed ring closure reaction for the thiazolidine-2-imine synthesis in a more modular and straightforward approach. The synthetic procedure reported herein represents a cleaner route toward thiazolidine-2-imines as compared to traditional methodologies. Moreover, the biological significance of combinatorially synthesized thiazolidin-2-imines has been investigated for their use as possible inhibitors for acetyl cholinesterase through molecular docking studies.
Copper-Catalyzed Aerobic Oxidative [3+2] Annulation for the Synthesis of 5-Amino/Imino-Substituted 1,2,4-Thiadiazoles through C-N/N-S Bond Formation
Yu, Wentao,Huang, Yubing,Li, Jianxiao,Tang, Xiaodong,Wu, Wanqing,Jiang, Huanfeng
, p. 9334 - 9343 (2018/07/30)
A copper-catalyzed aerobic oxidative annulation reaction of 2-aminopyridine/amidine with isothiocyanate has been reported. This strategy involving C-N/N-S bond formations provides various 5-amino/imino-substituted 1,2,4-thiadiazole derivatives under a Cu/O2 catalytic system. This method has demonstrated high reactivity, mild reaction conditions, and a broad substrate scope. Furthermore, the synthetic utilities of the approach are demonstrated by further modifications.
Nickle Catalysis Enables Access to Thiazolidines from Thioureas via Oxidative Double Isocyanide Insertion Reactions
Yuan, Wen-Kui,Liu, Yan Fang,Lan, Zhenggang,Wen, Li-Rong,Li, Ming
supporting information, p. 7158 - 7162 (2018/11/25)
An efficient synthesis of thiazolidine-2,4,5-triimine derivatives was developed via Ni-catalyzed oxidative double isocyanide insertion to thioureas under air conditions, in which thioureas play three roles as a substrate, a ligand, and overcoming isocyanide polymerization. The reaction is featured by employing a low-cost and low loading Ni(acac)2 catalyst, without any additives, and high atom economy. This is the first example to directly apply a Ni(II) catalyst in oxidative double isocyanide insertion reactions.
Blue-light induced CO releasing properties of thiourea based manganese(I) carbonyl complexes
Mansour, Ahmed M.,Friedrich, Alexandra
, p. 13 - 21 (2017/05/09)
A new class of blue-light triggered carbon monoxide releasing molecules based on Mn(CO)3Br(N,S) ((N,S)?=?N,S-bidentate thiourea ligands) has been reported in this work. The 1H and 13C NMR analysis indicated that the thioureas coordinate to Mn(I) in the thione form. The stability test and the ability to derive CO to DMSO and myoglobin solution upon the exposure to 468?nm light source have been investigated. The benzothiazole-thiourea-CORM released only one CO equivalent, while the pyridine-analogs offered two molecules at the same experimental conditions. Natural bond orbital analysis has been carried out to give details about the hybridization of Mn–C and C[tbnd]O bonds, natural charge, electronic arrangement of metal ion and strength of interaction between Mn(I) and the coordination sites. Both functional, B3LYP and CAM-B3LYP compare well with the experimental findings, where the longest wavelength band is assigned to MLCT.
ORGANIC MOLECULES FOR TERAHERTZ TAGGING APPLICATIONS
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Page/Page column 16, (2015/07/23)
The present invention discloses substituted heterocyclic compounds and /or aromatic compounds containing amide and/or urea groups exhibiting resonance in the range of 0.1- 10 THz. The invention also discloses binary molecular complexes based on the substituted heterocyclic compounds and/or aromatic compounds containing amide and/or urea groups of the present invention. The compounds and binary molecular complexes of the present invention have varying molecular mass and hydrogen bond strengths demonstrating several resonances below 10 THz. The compounds and binary molecular complexes of the present invention are customizable for various applications, such as authentication of a product.
Synthesis and in vitro urease inhibitory activity of N,N′- disubstituted thioureas
Khan, Khalid Mohammed,Naz, Farzana,Taha, Muhammad,Khan, Ajmal,Perveen, Shahnaz,Choudhary,Voelter, Wolfgang
, p. 314 - 323 (2014/02/14)
Thiourea derivatives (1-38) were synthesized and evaluated for their urease inhibition potential. The synthetic compounds showed a varying degree of in vitro urease inhibition with IC50 values 5.53 ± 0.02-91.50 ± 0.08 μM, most of which are superior to the standard thiourea (IC50 = 21.00 ± 0.11 μM). In order to ensure the mode of inhibition of these compounds, the kinetic study of the most active compounds has been carried out. Most of these inhibitors were found to be mixed-type of inhibitors, except compounds 13 and 30 which were competitive, while compound 19 was identified as non-competitive inhibitor with Ki values between 8.6 and 19.29 μM.
Synthesis and quantum calculations of 1,3-thiazoles and 1,3,4-thiadiazole derivatives via pyridinylthioureas
Dawood, Kamal M.,Mohamed, Adel A.,Alsenoussi, Mansour A.,Ibrahim, Ibrahim H.
, p. 383 - 394 (2013/09/23)
In this study, the reaction of 4- and 2-aminopyridines with phenyl isothiocyanate afforded the corresponding 1-phenyl-3-(pyridin-4-yl)thiourea 1 and its pyridin-2-yl analog 20. The reaction of 1 with ethyl chloroacetate gave 3-phenyl-2-(pyridin-4-ylimino)thiazolidin-4-one (3B), which upon a condensation reaction with aldehydes furnished 5-benzylidene derivatives 4a-c. Compounds 1 and 20 underwent heterocyclization upon their reaction with hydrazonoyl chloride 5 and gave the corresponding 1,3,4-thiadiazoles 8 and 22; however, the treatment of 1 and 20 with hydrazonoyl chloride 10 afforded the corresponding 1,3-thiazoles 14 and 25. The quantum calculations were studied using the density functional theory of the starting materials and some products.
