35572-08-8Relevant academic research and scientific papers
Consecutive C1-Homologation / Displacement Strategy for Converting Thiosulfonates into O,S-Oxothioacetals
Ielo, Laura,Pillari, Veronica,Miele, Margherita,Holzer, Wolfgang,Pace, Vittorio
, p. 5444 - 5449 (2020/10/12)
A conceptually intuitive synthesis of oxothioacetals is reported starting from thiosulfonates as electrophilic sulfur donors. The installation of a reactive CH2Cl motif with a homologating carbenoid reagent, followed by the immediate nucleophilic displacement with alcoholic groups [(hetero)-aromatic, aliphatic] offer a convenient access to the title compounds. Genuine chemoselectivity is uniformly observed in the case of multi-functionalized systems. (Figure presented.).
An expeditious and efficient bromomethylation of thiols: Enabling bromomethyl sulfides as useful building blocks
Silva-Cuevas, Carolina,Paleo, Ehecatl,León-Rayo, David F.,Lujan-Montelongo, J. Armando
, p. 24654 - 24659 (2018/07/25)
A facile and highly efficient method for the bromomethylation of thiols, using paraformaldehyde and HBr/AcOH, has been developed, which advantageously minimizes the generation of highly toxic byproducts. The preparation of 22 structurally diverse α-bromomethyl sulfides illustrates the chemo-tolerant applicability while bromo-lithium exchange and functionalization sequences, free radical reductions, and additions of the title compounds demonstrate their synthetic utility.
Anti-trypanosomatid benzofuroxans and deoxygenated analogues: Synthesis using polymer-supported triphenylphosphine, biological evaluation and mechanism of action studies
Castro, Diego,Boiani, Lucia,Benitez, Diego,Hernandez, Paola,Merlino, Alicia,Gil, Carmen,Olea-Azar, Claudio,Gonzalez, Mercedes,Cerecetto, Hugo,Porcal, Williams
experimental part, p. 5055 - 5065 (2010/01/16)
Hybrid vinylthio-, vinylsulfinyl-, vinylsulfonyl- and vinylketo-benzofuroxans developed as anti-trypanosomatid agents, against Trypanosoma cruzi and Leishmania spp., have showed low micromolar IC50 values. The synthetic route to access to these derivatives was an efficient Wittig reaction performed in mild conditions with polymer-supported triphenylphosphine (PS-TPP). Additionally, the benzofurozan analogues, deoxygenated benzofuroxans, were prepared using PS-TPP as reductive reagent in excellent yields. The trypanosomicidal and leishmanocidal activities of the benzofuroxan derivatives were measured and also some aspects of their mechanism of action studied. In this sense, inhibition of mitochondrial dehydrogenases activities, production of intra-parasite free radicals and cruzipain inhibition were studied as biological target for the anti-trypanosomatid identified compounds. The trypanosomicidal activity could be the result of both the parasite-mitochondrion function interference and production of oxidative stress into the parasite.
α-HALOGENO SULPHOXIDES AS AMBIDENT ELECTROPHILES TOWARDS DIALKYL PHOSPHITE ANIONS
Mikolajczyk, Marian,Zatorski, Andrzej
, p. 323 - 324 (2007/10/02)
α-Halogenomethyl alkyl(aryl) sulphoxides have been found to undergo nucleophilic attack by dialkyl phosphite anions at the α-carbon atom and/or at halogen.
Synthesis of α-Haloalkyl Esters from α-Arylthioalkyl Esters
Benneche, Tore,Strande, Per,Wiggen, Unni
, p. 74 - 77 (2007/10/02)
α-Monohaloalkyl esters have been prepared under mild conditions in high yields by selective cleavage of the carbon-sulfur bond in α-phenylthioalkyl esters using sulfuryl chloride or bromine.The intermediate α-phenylthioalkyl esters have been prepared by alkylation of the corresponding carboxylic acids with readily accessible α-haloalkyl phenyl sulphides.
Desilylative Pummerer-like Rearrangement of α-Trimethylsilyl-substituted Sulphoxides and Sulphides: Formation of α-Acyloxy and α-Halogeno Sulphides
Ishibashi, Hiroyuki,Nakatani, Hiroshi,Maruyama, Kazumi,Minami, Kenjiro,Ikeda, Masazumi
, p. 1443 - 1445 (2007/10/02)
α-Trimethylsilyl-substituted sulphoxides and sulphides undergo rearrangement with loss of the silyl group when treated respectively with trifluoroacetic anhydride and with N-halogenosuccinimide in the presence of trifluoroacetic acid, giving α-acyloxy sulphides and α-halogeno sulphides.
PREPARATION AND REACTIONS OF trans- (R = Me, Ph or C6H4Me-p)
McPherson, Helen,Wardell, James L.
, p. 261 - 266 (2007/10/02)
Formation of trans- (R=Me, Ph or C6H4Me-p) has been achieved by the oxidative addition of ClCH2SR to (PPh3)4Pt in refluxing PhH.The reaction of ClCH2SMe with (PMe2Ph)4Pt led to cis-.The reaction of trans-(PPh3)2Pt(CH2S
