17277-59-7Relevant academic research and scientific papers
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.
Co-production method of thionocarbamate and benzyl thioether acetic acid and application of the method
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Paragraph 0083; 0084, (2019/12/02)
The invention discloses a co-production method of thionocarbamate and benzyl thioether acetic acid and application of the method. The method comprises the following steps: with xanthate and benzyl chloride as initial raw materials, and performing esterification reaction to obtain benzyl xanthate; carrying out ammonolysis on benzyl xanthate by using primary amine to obtain thionocarbamate and benzyl mercaptan; further adding sodium chloroacetate into the mixture for reaction, thus generating benzyl thioether sodium acetate; finally, performing liquid separation to obtain the thionocarbamate collecting agent and a water phase containing benzyl thioether sodium acetate. The benzyl thioether sodium acetate-containing water phase can further react with benzyl chloride to obtain benzyl thioetherbenzyl acetate or be acidified and esterified with fatty alcohol to generate benzyl thioether alkyl acetate, and the two ester compounds can be subjected to hydroximation to synthesize benzyl thioether ethyl hydroximic acid. The method solves the problems of difficult recovery, difficult utilization and unpleasant smell of the byproduct sulfhydryl compound in the traditional thionocarbamate process, realizes co-production of benzyl thioether acetic acid and derivatives thereof, and improves the reaction efficiency.
2,5-DISUBSTITUTED 3-METHYL PYRAZINES AND 2,5,6-TRISUBSTITUTED 3-METHYL PYRAZINES AS ALLOSTERIC SHP2 INHIBITORS
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Paragraph 0700, (2018/03/26)
The present disclosure is directed to inhibitors of SHP2 and their use in the treatment of disease. Also disclosed are pharmaceutical compositions comprising the same.
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.
Mild Esterification of Carboxylic Acids via Continuous Flow Diazotization of Amines
Audubert, Clément,Lebel, Hélène
supporting information, p. 4407 - 4410 (2017/08/23)
A new continuous flow protocol for the diazotization of methylamine with 1,3-propanedinitrite in THF is reported. The synthesis of methyl esters was achieved in high yields from a variety of carboxylic acids in 20 min at 90 °C. Additionally, this protocol was extended to other aryl and alkyl amines, namely secondary amines, to produce various substituted esters in high yield using 2-MeTHF as a solvent. The reaction conditions were compatible with many functional groups, namely nitrogen-containing heterocycles, alkynes, alkenes, alcohols, and phenols. Mechanistic investigations reveal that the reaction appears to proceed through a transient diazonium species rather than a diazo intermediate.
Synthesis of Cyclic α-Diazo-β-keto Sulfoxides in Batch and Continuous Flow
McCaw, Patrick G.,Buckley, Naomi M.,Eccles, Kevin S.,Lawrence, Simon E.,Maguire, Anita R.,Collins, Stuart G.
, p. 3666 - 3679 (2017/04/11)
Diazo transfer to β-keto sulfoxides to form stable isolable α-diazo-β-keto sulfoxides has been achieved for the first time. Both monocyclic and benzofused ketone derived β-keto sulfoxides were successfully explored as substrates for diazo transfer. Use of continuous flow leads to isolation of the desired compounds in enhanced yields relative to standard batch conditions, with short reaction times, increased safety profile, and potential to scale up.
CARBOXYLIC DERIVATIVES FOR USE IN THE TREATMENT OF CANCER
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Page/Page column 97, (2009/07/25)
The invention provides novel compounds of formula (I), wherein: R1 is a radical derived from one of the known ring systems; R2 is a phenyl radical optionally substituted; Xn represents a birradical selected from the group consisting of: -(CH2)1-4-, (C2-C4)-alkenyl, (C2-C4)alkynyl, -S-(CH2)1-3-#, and -(CH2)1-3-O-#; wherein the symbol # indicates the position at which Xn is attached to R1; Yn is a birradical selected from the group consisting of: -(CH2)2-4-, -S-(CH2)1-3#, and -O-(CH2)1-3-#,; where in the symbol # indicates the position at which Yn is attached to R2; and R3 is a radical selected from the group consisting of: -OR4. The compounds of formula (I) are useful in the treatment of cancer
HISTONE DEACETYLASE INHIBITORS
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Page/Page column 30, (2008/06/13)
Hormone refractory metastatic disease can be treated with an oxyamide-containing compound through the inhibition of HDAC1 or HDAC2.
Spirocyclic Meisenheimer Complexes: XLIII. N-Picryl Derivatives of 1-Acyl-2-(alkylsulfonyl)hydrazines: Formation of Anionic Spirocomplex with Δ2-1,3,4-Oxadiazoline Ring, and Rearrangement
Knyzaev, V. N.,Borbulevich, O. Ya.,Shishkin, O. V.
, p. 1634 - 1641 (2007/10/03)
The reaction of N-[(benzylthio)acetyl]-N'-(alkylsulfonyl)hydrazines with picryl fluoride in the presence of triethylamine gives rise to regioselective formation of N-(alkylsulfonyl)-N-picryl-N'-[(benzylthio)acetyl]hydrazines that further transform into an
A simple and convenient method for preparation of sulfides
Feroci, Marta,Inesi, Achille,Rossi, Leucio
, p. 2611 - 2615 (2007/10/03)
Tetraethylammonium hydrogen carbonate (TEAHC) and tetraethylammonium carbonate (TEAC) obtained respectively by chemical and electrochemical way, react with thiols in acetonitrile affording, after addition of a suitable alkylating reagent, the corresponding sulfides in high to excellent yields.
