102-08-9Relevant articles and documents
Copper-Catalyzed Double Thiolation to Access Sulfur-Bridged Imidazopyridines with Isothiocyanate
Tian, Lu-Lu,Lu, Shuai,Zhang, Zhe-Hua,Huang, En-Ling,Yan, Hua-Ting,Zhu, Xinju,Hao, Xin-Qi,Song, Mao-Ping
, p. 5213 - 5221 (2019)
A copper(I)-catalyzed sulfur-bridged dimerization of imidazopyridines has been developed using isothiocyanate as the sulfur source. This method enables a switchable synthesis of bis(imidazo[1,2-a]pyridin-3-yl)sulfanes or bis(2-(imidazo[1,2-a]pyridin-2-yl)phenyl)sulfanes in the presence of 4-dimethylaminopyridine (DMAP) or K2CO3 when different imidazopyridines were employed. Under optimized conditions, a variety of sulfur-bridged imidazopyridines were obtained in good yields. Moreover, thiourea was proved to be the key intermediate under catalytic system A.
-
Chattopadhyaya,Rao
, p. 289 (1974)
-
Rapid synthesis of a 13C6-benzothiazolium salt from 13C6-aniline
Galliford, Chris V.,Voronin, Kimberly,Hesk, David,Koharski, David,McNamara, Paul
, p. 229 - 232 (2011)
13C6-labeled aniline was used as a starting material for the facile synthesis of 13C6-benzothiazolium salt (1). Copyright
Barbiturate squaraine dyes as fluorescent probes for serum albumins detection
Almeida, Paulo,Boto, Renato E. F.,Gomes, Vanessa S. D.,Gon?alves, Helena M. R.,Reis, Lucinda V.
, (2020)
Three indolenine-based barbiturate squaraine dyes were synthesized, characterized and subjected to photophysical studies, including their affinity with human serum albumin and bovine serum albumin as protein models in phosphate buffer solution. All dyes successfully interact with both proteins with high affinity binding constants. It was found that dyes with hydrophobic substituents had superior binding constants with both proteins. The fluorescence intensity of all dyes increased in the presence of both proteins which allowed the determination of detection and quantifications limits in the tens of nanomolar, using a protein concentration of 0–3.5 μM. Concerning to the study on the binding sites of the synthesized dyes using the warfarin and ibuprofen markers, the results of this study suggest that, one dye binds to both BSA binding sites while the two others dyes binds only to site I, and that all three dyes bind to both HSA binding sites.
-
Feuer,Braunstein
, p. 2024 (1969)
-
Structural requirement of phenylthiourea analogs for their inhibitory activity of melanogenesis and tyrosinase
Thanigaimalai, Pillaiyar,Lee, Ki-Cheul,Sharma, Vinay K.,Joo, Cheonik,Cho, Won-Jea,Roh, Eunmiri,Kim, Youngsoo,Jung, Sang-Hun
, p. 6824 - 6828 (2011)
Effect of a series of 1-phenylthioureas 1a-k and 1,3-disubstituted thioureas 2a-k were evaluated against melanin formation in melanoma B16 cell line and mushroom tyrosinase. Inhibitory activity of tyrosinase of 1-phenylthioureas 1a-k is parallel to their melanogenic inhibition. Thus, the melanogenic inhibition in melanoma B16 cells of 1-phenylthioureas could be the result of inhibition of tyrosinase. However, 1,3-diaryl or 1-phenyl-3- alkylthioureas, 2a-k, appears as melanogenic inhibitor without inhibition of tyrosinase. The molecular docking study of 1e and 2b to binding pocket of tyrosinase provided convincing explanation regarding the necessity of direct connection of planar phenyl to thiourea unit without N′-substitution of phenylthioureas 1 as tyrosinase inhibitor and 2 as non-tyrosinase inhibitor.
A CONVENIENT METHOD FOR THE PREPARATION OF N,N'-DISUBSTITUTED THIOUREAS USING 2-CHLOROPYRIDINIUM SALT, SODIUM TRITHIOCARBONATE AND AMINES
Takikawa, Yuji,Inoue, Noriyuki,Sato, Ryu,Takizawa, Saburo
, p. 641 - 642 (1982)
N,N'-Disubstituted thioureas were prepared in high yields by treating 2-chloropyridinium salt with sodium trithiocarbonate and subsequently adding amines.
-
Hodgkins,Reeves
, p. 3098 (1964)
-
A convenient route to substituted thiocarbamides
Ramadas,Srinivasan
, p. 3381 - 3387 (1995)
-
Unclicking of thioureas: Base catalyzed elimination of anilines and isothiocyanates from thioureas
Vlatkovi?, Matea,Feringa, Ben L.
, p. 2188 - 2192 (2019)
Bisaromatic thioureas are widely used in e.g. asymmetric organocatalysis and considered to be robust compounds. Herein we show, in strong contrast to common notion, that thioureas dissociate to amines and isothiocyanates in a base catalyzed reaction under mild conditions. This ‘unclicking’ process can occur in the presence of weak organic bases even at moderate temperatures. The influence of the substituents at the aromatic rings of the thiourea on the regioselectivity of this unclicking process is also shown.
A general and facile one-pot process of isothiocyanates from amines under aqueous conditions
Sun, Nan,Li, Bin,Shao, Jianping,Mo, Weimin,Hu, Baoxiang,Shen, Zhenlu,Hu, Xinquan
, p. 61 - 70 (2012)
A general and facile one-pot protocol for the preparation of a broad range of alkyl and aryl isothiocyanates has been developed from their corresponding primary amines under aqueous conditions. This synthetic process involves an in situ generation of a dithiocarbamate salt from the amine substrate by reacting with CS2 followed by elimination to form the isothiocyanate product with cyanuric acid as the desulfurylation reagent. The choice of solvent is of decisive importance for the successful formation of the dithiocarbamate salt particularly for highly electron-deficient substrates. This novel and economical method is suitable for scale-up activities.
Carbon tetrabromide promoted reaction of amines with carbon disulfide: Facile and efficient synthesis of thioureas and thiuram disulfides
Liang, Fushun,Tan, Jing,Piao, Chengri,Liu, Qun
, p. 3579 - 3584 (2008)
A novel carbon tetrabromide promoted one-pot reaction of amines and carbon disulfide under mild conditions has been developed, which provides a straightforward and efficient access to thioureas and thiuram disufides, depending on the nature of the amines employed. The promotion effect is explained as the transient formation of a sulfenyl bromide intermediate from dithiocarbamate and carbon tetrabromide during the reaction. Georg Thieme Verlag Stuttgart · New York.
-
Shahak,Sasson
, p. 3440 (1973)
-
Quantitative estimation of the α-effect in the reactions yielding phosphorus-containing thiosemicarbazides
Yanchuk
, p. 1240 - 1242 (2006)
The α-effect in the reactions of O,O-diaryl phosphorohydrazidothioates with phenyl isothiocyanate in benzene at 25°C was quantitatively evaluated from the kinetic data. The probable reaction mechanism was suggested, and the causes of the α-effect in these reactions are discussed. An approximate linear correlation is observed between the α-effect in the reactions of O,O-diaryl phosphorohydrazidothioates with phenyl isothiocyanate, basicity constants of the hydrazides, and σp constants of the substituents at the P atom. The value of the α-effect is largely determined by the structure of the transition state. Nauka/Interperiodica 2006.
-
Helgen et al.
, p. 884 (1959)
-
CuI-catalyzed sulfenylation of 1-aryl trifluoromethyl pyrazolones: Direct formation of C-S-C bond using aryl iodides and carbon disulfide
Avalani, Jemin R.,Kamani, Ronak D.,Prajapati, Ronak V.,Prajapati, Vaibhav D.,Purohit, Vishal B.,Raval, Dipak K.,Sapariya, Nirav H.
supporting information, (2021/11/20)
A novel approach for CuI-catalyzed sulfenylation of 1-aryl-3-trifluoromethyl pyrazolones (2a-d) with aryl iodides (1a-j) and carbon disulfide as sulfenylating agent has been described. The protocol was found to be simple and efficient benign to access a broad array of fluorinated sulfenyl pyrazolones in good yields. The formation of C-S-C bond was achieved by using inexpensive and readily available starting materials.
The coordination chemistry of sulfonyl-substituted thioureas towards the d8 metal centres platinum(II), palladium(II), nickel(II) and gold(III)
Henderson, William,Risi, Matthew C.,Saunders, Graham C.
, (2021/07/13)
Reactions of the complexes cis-[PtCl2(PPh3)2], [PtCl2(dppp)] (dppp = Ph2P(CH2)3PPh2), [MCl2(dppe)] (dppe = Ph2P(CH2)2PPh2, M = Ni, Pd), [PdCl2(bipy)] (bipy = 2,2′-bipyridine) and [AuCl2(bp)] (bp = cyclometallated 2-benzylpyridine) with p-TolSO2NHC(S)NHPh and Et3N in refluxing methanol gave a series of new thiourea complexes containing the ligand bound as a dianion through the S and the NPh groups. The related thioureas RSO2NHC(S)NHPh (R = Me, Et) and p-TolSO2NHC(S)NHCH2CH=CH2 were also reacted with cis-[PtCl2(PPh3)2] to form the corresponding complexes [Pt{RSO2NC(S)NPh}(PPh3)2] and [Pt{TolSO2NC(S)NCH2CH=CH2}(PPh3)2] respectively. X-ray structure determinations were carried out on the thiourea MeSO2NHC(S)NHPh and its platinum complex [Pt{MeSO2NC(S)NPh}(PPh3)2], as well as [Pt{TolSO2NC(S)NPh}(PPh3)2]. Both complexes form the distal isomer with a remote NSO2R group, and no evidence was observed for isomerisation of these platinum complexes in solution. The palladium complexes [Pd{TolSO2NC(S)NPh}L2] [L2 = Ph2PCH2CH2PPh2 (dppe), or 2,2′-bipyridine (bipy)] undergo decomposition in solution to form the sulfide-bridged aggregates [Pd3S2(L2)3]2+, identified by ESI MS and 31P NMR.
Identification of organophosphorus simulants for the development of next-generation detection technologies
Ellaby, Rebecca J.,Clark, Ewan R.,Allen, Nyasha,Taylor, Faith R.,Ng, Kendrick K. L.,Dimitrovski, Milan,Chu, Dominique F.,Mulvihill, Daniel P.,Hiscock, Jennifer R.
, p. 2008 - 2014 (2021/03/16)
Organophosphorus (OP) chemical warfare agents (CWAs) represent an ongoing threat but the understandable widespread prohibition of their use places limitations on the development of technologies to counter the effects of any OP CWA release. Herein, we describe new, accessible methods for the identification of appropriate molecular simulants to mimic the hydrogen bond accepting capacity of the PO moiety, common to every member of this class of CWAs. Using the predictive methodologies developed herein, we have identified OP CWA hydrogen bond acceptor simulants for soman and sarin. It is hoped that the effective use of these physical property specific simulants will aid future countermeasure developments.