52626-38-7Relevant academic research and scientific papers
Synthesis of nitrophenyl-substituted 1,3-thiazoline-2-thiones by oxirane ring opening with several dithiocarbamates
Kulakov,Gazaliev,Nurkenov,Turdybekov
, p. 490 - 494 (2010)
Thiazolo-2(3H)-thiones have been prepared by the reaction of triethylamine dithiocarbamates and 4-nitrophenyloxirane via formation of intermediate 2-hydroxy-2-(4-nitrophenyl)ethyldithiocarbamates with simultaneous dehydrogenation of the thiazolidine ring to a thiazoline. It was found that both the basicity of the starting amines and the temperature influenced the course of the reaction.
Na2S2O8-mediated efficient synthesis of isothiocyanates from primary amines in water
Fu, Zhicheng,Yuan, Wenhao,Chen, Ning,Yang, Zhanhui,Xu, Jiaxi
, p. 4484 - 4491 (2018/10/17)
We have developed two green, practical, and efficient procedures, including a one-pot one, to synthesize isothiocyanates from amines and carbon disulfide via desulfurization with sodium persulfate. Water is used as the solvent. Basic conditions are necessary for good chemoselectivity for isothiocyanates. Structurally diverse linear and branched alkyl amines and aryl amines are readily converted to isothiocyanates by the two procedures in satisfactory yields. Halogens, benzylic C-H bonds, methylthio, nitro, ester, alkenyl, electron-rich or -deficient (hetero)aryls, acetylenyl, and even phenolic and alcoholic hydroxyls are well tolerated. The one-pot procedure in water can also be used to realize the preparation of chiral isothiocyanates from chiral amines, and the modification of bioactive structures with free amino groups. In large-scale preparation, simple and practical purification procedures independent of column chromatography are developed.
Synthesis of potential plant protecting compounds on the basis of 2,3-dihydrothiazol-2-thione. I. Change in structure at the N3 and C4
Hanefeld, Wolfgang,Wurtz, Stephan
, p. 355 - 370 (2007/10/03)
A considerable number of potential plant protecting compounds with the core structure of 2,3-dihydrothiazol-2-thione has been prepared by the reaction of dithiocarbamates with halomethylcarbonyl compounds forming N-substituted 4-substituted 4-hydroxythiazolidin-2-thiones 2-4, which can split off water to yield 5. The structural variability at N3 is given either by the amine used for dithiocarbamate synthesis or by acylation of N-unsubstituted 2,3-dihydrothiazol-2-thiones like 4i. The variability at C4 is either achieved by the kind of the halomethylcarbonyl compound or by reactions of 4:chloromethyl derivatives 5, which can be transformed by a number of nucleophilic reagents to derivatives like thioethers 8, ethers 9, amines 10, nitriles 11, azides 12a, thiocyanates 12b, the primary amine 14 and derived from that the amides 15 or the ureas 16. Wiley-VCH Verlag GmbH, 2000.
