10230-69-0Relevant articles and documents
A new method for the reductive cleavage of S-S bond by the system of Cp2TiCl2/i-BuMgBr/THF and its application in synthesis of α-alkylthio carbonyl compounds
Huang,Zheng
, p. 1297 - 1301 (1999)
The reduction of disulfides by Cp2TiCl2/i-BuMgBr/THF led to nucleophilic sulfides [Cp2TiSR]. This species reacted with α-bromo carbonyl compounds to give α-alkylthio carbonyl compounds in high yields.
Selective synthesis of α-organylthio esters and α-organylthio ketones from β-keto esters and sodium S-organyl sulfurothioates under basic conditions
Kazmierczak, Jean C.,Cargnelutti, Roberta,Barcellos, Thiago,Silveira, Claudio C.,Schumacher, Ricardo F.
supporting information, p. 234 - 244 (2021/02/27)
We described herein a selective method to prepare α-organylthio esters and α-organylthio ketones by the reaction of β-keto esters with sodium S-benzyl sulfurothioate or sodium S-alkyl sulfurothioate (Bunte salts) under basic conditions in toluene as the solvent at 100 °C. When 4 equivalents of a base were used, a series of differently substituted α-thio esters were obtained with up to 90% yield. On the other hand, employing 2 equivalents of a base, α-thio ketones were achieved after 18 h under air. Furthermore, after a shorter reaction time, the isolation of keto-enol tautomers was possible, revealing them as significant intermediates for the mechanism elucidation.
Thiol-free chemoenzymatic synthesis of β-ketosulfides
Heredia, Adrián A.,López-Vidal, Martín G.,Kurina-Sanz, Marcela,Bisogno, Fabricio R.,Pe?é?ory, Alicia B.
supporting information, p. 378 - 387 (2019/02/20)
A preparation of β-ketosulfides avoiding the use of thiols is described. The combination of a multicomponent reaction and a lipase-catalysed hydrolysis has been developed in order to obtain high chemical diversity employing a single sulfur donor. This methodology for the selective synthesis of a set of β-ketosulfides is performed under mild conditions and can be set up in one-pot two-step and on a gram-scale.
Preparation method and application of novel ionic binuclear Schiff base titanium complex
-
Paragraph 0083; 0084, (2018/04/03)
The invention provides a preparation method of a novel ionic binuclear Schiff base titanium complex and a synthetic method of applying the novel ionic binuclear Schiff base titanium complex to catalyze zinc powder and reduce disulfide or selenide to prepare sulfo(seleno) ester and dissymmetric sulfoether(selenide). The complex is a cationic binuclear Schiff base titanium complex, wherein titaniumatoms are bridged by oxygen atoms and are coordinated with a Schiff base ligand and a hydrone, and an ionic bond is formed by a cation part and an anion part of whole Schiff base titanium. The ionic binuclear Schiff base titanium complex is used as a catalyst, the zinc powder is used as a reducer, the disulfide(selenide) can be reduced and fractured, and the disulfide(selenide) can further and respectively react with anhydride, an alpha-bromo carbonyl compound and bromoalkane to prepare the sulfo(seleno) ester and the dissymmetric sulfoether(selenide). According to the preparation method provided by the invention, the defects that traditional lewis acid halide is deliquescent, an absolute solvent is used, conditions are strict and the like are overcome; an effective path for reducing the disulfide or selenide to prepare the sulfo(seleno) ester and the dissymmetric sulfoether(selenide) is provided, and the preparation method has the advantages of high yield, simpleness in operation andthe like.
Stevens rearrangement of thioethers with arynes: A facile access to multi-substituted β-keto thioethers
Xu, Xiao-Bo,Lin, Zi-Hua,Liu, Yuyin,Guo, Jian,He, Yun
supporting information, p. 2716 - 2720 (2017/04/03)
An effective method for the synthesis of multi-substituted β-keto thioethers via Stevens rearrangement of simple β-keto thioethers with arynes has been developed. In these reactions, successive C-S/C-H/C-C bonds were formed in one pot under mild and transition-metal free conditions to afford multi-substituted β-keto thioethers in moderate to good yields.
One-step synthesis of N-acetylcysteine and glutathione derivatives using the Ugi reaction
Zhdanko, Alexander G.,Gulevich, Anton V.,Nenajdenko, Valentine G.
experimental part, p. 4692 - 4702 (2009/10/02)
Fully protected natural and unnatural N-acetylcysteine, dipeptide Cys-Gly, glutathione, and homoglutathione derivatives were synthesized by the Ugi four-component reaction using various benzylthio aldehydes and ketones as carbonyl building blocks. The scope and limitations of the method were investigated. Formation of imidazoline by-products in the Ugi reaction was discussed. 2,2,2-Trifluoroethanol was shown to be a superior reaction media than methanol in some reactions. Also, the 4-methyl-2,6,7-trioxabicyclo[2.2.2]octyl derivative (OBO-ester) of isocyanoacetic acid was shown to be superior to use than ethyl isocyanoacetate as a peptide synthesis precursor in cases when higher reactivity of an isocyanide is required.
NOVEL INDOLE DERIVATIVES AS SELECTIVE ANDROGEN RECEPTOR MODULATOR (SARMS)
-
Page/Page column 48, (2008/06/13)
The present invention is directed to novel indole derivatives, pharmaceutical compositions containing them and their use in the treatment of disorders and conditions modulated by the androgen receptor.
Humicola lanuginosa lipase-catalyzed enantioselective resolution of β-hydroxy sulfides: Versatile synthons for enantiopure β-hydroxy sulfoxides
Singh, Satwinder,Kumar, Subodh,Chimni, Swapandeep Singh
, p. 2457 - 2462 (2007/10/03)
Humicola lanuginosa lipase-catalyzed acylation of β-hydroxy sulfides provides both the (R)- and (S)-enantiomers in high enantiomeric purity. In two cases the resolved hydroxy sulfides were oxidized to give β-hydroxy sulfoxides in >99% e.e. The effect of substituents on enantioselectivity is discussed.
Intramolecular rhodium carbenoid insertions into aromatic C-H bonds. Preparation of 1,3-dihydrothiophene 2,2-dioxides fused onto aromatic rings
Babu, Suresh D.,Hrytsak, Michael D.,Durst, Tony
, p. 1071 - 1076 (2007/10/02)
The preparation of 1-carboalkoxy-1,3-dihydrobenzenothiophene 2,2-dioxides via rhodium acetate or rhodium trifluoro-acetate catalyzed decomposition of α-diazo-β-arylmethanesulfonyl esters is described.The reaction has been extended to yield 1,3-dihydrothiophene 2,2-dioxides fused to the 2,3 position of thiophene and indole, but not of furans.In the latter case products derived from the opening of the furan ring were obtained.Key words: synthesis, 1-carboalkoxy-1,3-dihydrobenzothiophene 2,2-dioxides, intramolecular carbenoid insertions, rhodium acetate catalysis.
α-Thio-substituted Ketones as Precursors of Olefins via Oxathiolanes: Benzyl as Protecting Group
Brown, Michael D.,Whitham, Gordon H.
, p. 817 - 822 (2007/10/02)
The feasibility of a regiospecific synthesis of tetrasubsituted olefins starting from protected α-thiol substituted ketones has been demonstrated by three examples.The approach (see Scheme) involves: S-activated alkylation (i), carbonyl addition of an organometallic reagent (ii), deprotection (iii), formation of a 2-phenyloxathiolane (iv), and base-promoted cycloelimination (v).An unsatisfactory feature is the lack of stereochemical control in step (ii).An attempt to telescope steps (iii) and (iv) by sequential Pummerer reaction-cyclisation at the β-benzylthio alcohol stage was unsuccessful.
