7250-18-2Relevant academic research and scientific papers
Synthetic method of dialkyl amino dithiocarbamate alkyl ester
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Paragraph 0010-0016; 0072-0076, (2020/02/04)
In organic sulfur compounds, dialkyl amino dithiocarbamate alkyl ester plays a very important role. Researches show that dialkyl amino dithiocarbamate alkyl ester and the derivatives thereof have widebiological characteristics and pharmacological activity. For example, many studies show that the dialkyl amino dithiocarbamate alkyl ester has various activities, including anti-proliferative, anti-glaucoma, antibacterial, antifungal, breast cancer treatment and cholinesterase inhibition activities, and can be used as a myocardial imaging agent. It is known that dialkyl amino dithiocarbamate alkyl ester and the derivatives thereof can be taken as inhibitors of HIV-1 NCp7, antiviral agents, and non-flavonoid TRPV1 antagonists. Dialkyl amino dithiocarbamate alkyl ester has a wide application range, and is massively produced in the world. The invention provides a method for efficiently synthesizing dialkyl amino dithiocarbamate alkyl ester. Under the catalysis of CuI, a chiral quaternary ammonium salt and a dialkyl amino dithioformate are used for C-S cross coupling for the first time, and dialkyl amino dithiocarbamate alkyl ester is prepared. The target product is further converted andcoupled with brominated aromatic hydrocarbons to obtain high-purity enantiomer chiral thioethers. The synthesis process has the advantages of mild reaction conditions, wide universality, no toxicity or danger, high yield, wide substrate range and the like.
Iodine mediated direct coupling of benzylic alcohols with dithiocarbamate anions: An easy access of S-benzyl dithiocarbamate esters under neat reaction condition
Dutta, Soumya,Saha, Amit
, (2020/09/10)
An efficient, metal and solvent free synthesis of S-benzylic dithiocarbamate esters has been demonstrated via the iodine mediated direct C-S coupling of benzylic alcohols with dithiocarbamate anions generated in-situ by the reactions of amines and carbon disulphide. All the reactions were very fast (15–30 min) and performed under open air atmosphere. Cyclic and acyclic secondary amines, primary amine, aromatic amine actively participated in the one-pot coupling reactions with different benzylic alcohols. Non benzylic alcohols offer the synthesis of O-thiocarbamate compounds under the identical reaction condition.
Transition-Metal-Free C(sp3)–S Coupling in Water: Synthesis of Benzyl Dithiocarbamates Using Thiuram Disulfides as an Organosulfur Source
Peng, Han-Ying,Dong, Zhi-Bing
, p. 949 - 956 (2018/11/27)
A simple, highly efficient and environmentally benign method for the synthesis of benzyl dithiocarbamates was reported. Without addition of metal catalyst, a series of 34 benzyl dithiocarbamates were obtained in good to excellent yields by treating benzyl halides with tetraalkylthiuram disulfides in water. The protocol allows easy access to C(sp3)–S bond formation, features the advantages of easy performance, environmental friendliness, good to excellent yields, and good functional tolerance, showing potential value for the preparation of some biologically active compounds.
An Efficient Synthesis of Benzyl Dithiocarbamates by Base-Promoted Cross-Coupling Reactions of Benzyl Chlorides with Tetraalkylthiuram Disulfides at Room Temperature
Wu, Zhiyong,Lai, Miao,Zhang, Siyuan,Zhong, Xianyun,Song, Hao,Zhao, Mingqin
supporting information, p. 7033 - 7036 (2019/01/04)
A straightforward, mild and efficient protocol for the synthesis of benzyl dithiocarbamates from benzyl chlorides and tetraalkylthiuram disulfides is presented. This protocol is compatible with a wide variety of electron-donating and -withdrawing substituents and enables construction of various dithiocarbamate derivatives from readily available starting materials.
Direct conversion of methylarenes into dithiocarbamates, thioamides and benzyl esters
Guntreddi, Tirumaleswararao,Vanjari, Rajeshwer,Singh, Krishna Nand
, p. 3887 - 3892 (2014/06/09)
A new strategy for the synthesis of a variety of dithiocarbamates and thioamides has been developed employing inexpensive and readily available methylarenes under metal-free and solvent-free conditions. The approach offers a one-pot procedure and has also been extended to the synthesis of a diverse range of benzyl esters.
Highly stereoselective access to sulfur derivatives starting from zinc organometallics
Krasovskiy, Arkady,Gavryushin, Andrey,Knochel, Paul
, p. 792 - 794 (2007/10/03)
A number of organozinc reagents was found to react with tetramethylthiuram disulfide [(Me2NCS2)2] giving dithio-carbamates with complete retention of configuration in the case of chiral compounds. Georg Thieme Verlag Stuttgart.
Synthesis of dithiocarbamates and selenothiocarbamates
Koketsu, Mamoru,Otsuka, Toshihiro,Ishihara, Hideharu
, p. 443 - 448 (2007/10/03)
Several dithiocarbamates and selenothiocarbamates were synthesized by the reaction of N,N-dimethylthiocarbamoyl chloride with the corresponding thiolates and selenolates.
Thiocyanation of alkyl halides with alkyl thiocyanates in the presence of quaternary phosphonium halides
Ohtani, Noritaka,Murakawa, Shigeki,Watanabe, Kohji,Tsuchimoto, Daisuke,Sato, Daiki
, p. 1851 - 1856 (2007/10/03)
Alkyl thiocyanates undergo simple SN2 reactions with the counter ions of quaternary phosphonium salts in nonpolar solvents and thiocyanate ions are liberated as the leaving ion. Depending on the nucleophile, the reaction proceeded irreversibly or reversibly. The reaction of benzyl thiocyanate with azide ions afforded a quantitative yield of benzyl azide. The reactions of alkyl thiocyanates with halide ions gave an equilibrium mixture where the reverse reaction of the alkyl halides produced with the liberated thiocyanate ions took place simultaneously. Thus, thiocyanate-halide exchange reactions between an alkyl thiocyanate and an alkyl halide were possible in the presence of a catalytic amount of a quaternary salt.
ONE-STEP STEREOSPECIFIC CONVERSION OF ALCOHOLS INTO DITHIOCARBAMATES : A SMOOTH PATHWAY FOR THE INTRODUCTION OF A SULPHUR FUNCTIONALITY.
Rollin, P.
, p. 4169 - 4170 (2007/10/02)
Functionally diverse dithiocarbamates were prepared from the corresponding alcohols in a mild high-yielding one-pot synthesis involving unexpensive ziram (zinc N,N-dimethyldithio carbamate) in a stereospecific Mitsunobu type procedure.
Dithioallophanic Acids. Part-III: Interaction of Carbon Oxysulphide with 2-S-benzyl-1,1-Dimethyl/1-Phenyl Isothiocarbamides
Dravid, R. N.,Chande, M. S.
, p. 855 - 857 (2007/10/02)
Interaction of carbon oxysulphide with 2-S-benyl-1,1-dimethtyl isothiocarbamide in benzene has been found to afford 1,1-dimethyl thiocarbamide thiocyanate, S-benzyl-N,N-dimethyl thiocarbamate, and S-benzyl-N,N-dimethyl dithiocarbamate. 2-S-Benzyl-1-phenyl isothiocarbamide also affords the corresponding thiocarbamate, dithiocarbamate and in addition phenyl thiocarbamide.Mechanism has been discussed in detail.
