43009-20-7Relevant academic research and scientific papers
Masked thiol sugars: Chemical behavior and synthetic applications of S-glycopyranosyl-N-monoalkyl dithiocarbamates
Megia-Fernandez, Alicia,De La Torre-Gonzalez, Diego,Parada-Aliste, Jose,Lopez-Jaramillo, Francisco Javier,Hernandez-Mateo, Fernando,Santoyo-Gonzalez, Francisco
, p. 620 - 631 (2014)
The chemical behavior of S-glycopyranosyl-N-monoalkyl dithiocarbamates (DTCs) as masked 1-glycosyl thiols, easily prepared by the nucleophilic displacement of 1-halo sugars with dithiocarbamate salts of primary amines, has been studied and synthetically exploited. This behavior relies on the abstraction of the proton of the carbamate functionality that allows controlled access to thiolate sugar intermediates. The basic character of the DTC salts used as reagents leads to thiolates that evolve in situ to symmetrical diglycosyldisulfides (DGDSs) when long reaction times are allowed. Alternatively, controlled unmasking of the thiolate function can be efficiently attained by treatment with an external base of isolated anomeric glycosyl DTCs, the formation of which is prevalent when using short reaction times. In this manner, a second methodology for the preparation of symmetrical DGDSs and a chemical protocol for the S-glycosylation of any electrophilic substrate are established. The applications of this last strategy for the preparation of thioglycosyl vinyl sulfones, thiodisaccharides, and S-linked homo- and heterodivalent neoglycoconjugates are described as a proof-of-concept of the great potential of the sugar DTCs in any chemical scenario in which the covalent attachment of a thiol sugar is required. The evaluation of the biological functionality of some divalent sulfurated sugar systems is also described. Copyright
Heterocyclic iodoniums as versatile synthons to approach diversified polycyclic heteroarenes
Zhu, Daqian,Wu, Zhouming,Liang, Liyun,Sun, Yameng,Luo, Bingling,Huang, Peng,Wen, Shijun
, p. 33170 - 33179 (2019)
Polycyclic heteroarenes are important scaffolds in the construction of pharmaceuticals. We have previously developed a series of novel heterocyclic iodoniums. In our current work, these unique iodoniums were employed to construct various complex polycycli
Direct, Microwave-Assisted Synthesis of Isothiocyanates
Janczewski, ?ukasz,Gajda, Anna,Gajda, Tadeusz
supporting information, p. 2528 - 2532 (2019/04/03)
A microwave-assisted desulfuration of readily available dithiocarbamates, formed in situ from primary amines, leading to target isothiocyanates has been developed. This efficient protocol provides a rapid, environmentally benign route to aliphatic and aromatic isothiocyanates.
T3P - A Benign Desulfurating Reagent in the Synthesis of Isothiocyanates
Janczewski, ?ukasz,Gajda, Anna,Frankowski, Sebastian,Goszczyński, Tomasz M.,Gajda, Tadeusz
, p. 1141 - 1151 (2017/12/06)
A number of alkyl, aryl and bifunctional isothiocyanates are obtained in moderate to high yields (41-94%) in a two-step, one-pot reaction of the parent primary amines or their salts with carbon disulfide, followed by reaction of the thus formed dithiocarbamates with T3P (propane phosphonic acid anhydride) as a new and efficient desulfurating agent.
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.
Copper promoted desulfurization towards the synthesis of isothiocyanates
Mandapati, UshaRani,Pinapati, Srinivasarao,Rudraraju, RameshRaju
supporting information, p. 125 - 128 (2016/12/26)
The cheap, readily available and air stable catalyst was used as the desulfurization agent for the conversion of aniline to isothiocyanates in one pot two step reaction under mild reaction conditions.
N-Benzyldithiocarbamate Salts as Sulfur Sources to Access Tricyclic Thioheterocycles Mediated by Copper Species
Luo, Bingling,Cui, Qingbin,Luo, Hongwen,Hu, Yumin,Huang, Peng,Wen, Shijun
supporting information, p. 2733 - 2738 (2016/09/13)
Using an easily prepared triethylammonium N-benzyldithiocarbamate salt as a sulfur source, a dual C?S functionalization of cyclic diaryliodoniums to form tricyclic thioheterocycles is realized. Our method uses the readily available copper sulfate to accelerate the chemical transformation under mild conditions. A broad range of cyclic diaryliodoniums with a ring size from 5- to 7-membered can be employed to gain a quick access to tricyclic thioheterocycles including dibenzothiophenes, thioxanthenes, and phenoxathiines. (Figure presented.).
NMR study of the naphtho-1,3-dithioles formed from carbamodithioates and 2,3-dichloro-1,4-naphthoquinone
Aly, Ashraf A.,Brown, Alan B.,El-Shaieb, Kamal M.,Hassan, Alaa A.,Bedair, Tarek M.L.
scheme or table, p. 689 - 691 (2010/04/26)
Reaction of triethylammonium 1,2-ethanediylbis(carbamodithioate) with 2,3-dichloro-1,4-naphthoquinone in DMF furnished N,N′-ethylenebis(2- iminonaphtho[2,3-d][1,3]dithiole-4,9-dione) in 94% yield. Triethylammonium N-arylcarbamodithioates reacted with 2,3-
A one-pot preparation of cyanamide from dithiocarbamate using molecular iodine
Nath, Jayashree,Patel, Bhisma K.,Jamir, Latonglila,Sinha, Upasana Bora,Satyanarayana
supporting information; experimental part, p. 1503 - 1506 (2010/05/18)
An efficient one-pot method for the synthesis of cyanamides from dithiocarbamate salts via a double desulfurization strategy using molecular iodine is disclosed. Dithiocarbamates, by the action of iodine yield isothiocyanates in situ, which on treatment with aqueous NH3 give thioureas. The thioureas so generated undergo further oxidative desulfurization with I2 giving corresponding cyanamides in good yields. Environmental benignity, cost effectiveness and high yields are the important attributes of this one pot procedure. The Royal Society of Chemistry 2009.
