80095-81-4Relevant academic research and scientific papers
Base-Catalyzed Transesterification of Thionoesters
Newton, Josiah J.,Britton, Robert,Friesen, Chadron M.
, p. 12784 - 12792 (2018/10/20)
Here we report a convenient synthesis of thionoesters by base-catalyzed transesterification. Benzyl and alkyl thionobenzoates and thionoheterobenzoates were efficiently prepared using various alcohols catalyzed by the corresponding sodium alkoxide. This methodology features a broad substrate scope, good to excellent yields, short reaction times, while simultaneously driving the reaction toward completion through the removal of the methanol byproduct. We also report the conversion of a small collection of thionobenzoates into the corresponding α,α-difluorobenzyl ethers to demonstrate the conversion of alcohols into difluorobenzyl or difluoroheterobenzyl ethers, a process that could prove useful for lead optimization in medicinal chemistry.
Imidazolinium and amidinium salts as Lewis acid organocatalysts
Sereda, Oksana,Clemens, Nicole,Wilhelm, Rene,Heckel, Tatjana
supporting information, p. 1798 - 1803,6 (2020/09/16)
The application of imidazolinium and amidinium salts as soft Lewis acid organocatalysts is described. These salts were suitable catalysts for the activation of unsaturated thioesters in a Diels-Alder reaction and in the ring opening of thiiranes and epoxi
Thiono- and Dithioesters, 47. - α,β-Unsaturated Thiono- and Dithioesters by Condensation Reactions
Hartke, Klaus,Kunze, Olaf
, p. 321 - 330 (2007/10/02)
Condensation of (dimethoxyphosphinyl)thionoacetate 4 (X=O) and -dithioacetate 4 (X=S) with aldehydes, catalysed by aqueous potassium carbonate, leads in a Horner-Wittig reaction to the formation of the α,β-unsaturated thionoesters 5a-o and dithioesters 6a
ALDOLIC CONDENSATIONS ON INORGANIC SOLID SUPPORT: APPLICATION TO THE SYNTHESIS OF O-ETHYL ESTERS OF 3-PHENYL-2-PROPENETHIOIC ACIDS.
Davrinche, Catherine,Brion, Jean-Daniel,Reynaud, Pierre
, p. 1181 - 1190 (2007/10/02)
Aldolic condensations with O-ethyl thioesters are performed on basic alumina to give 2,3-unsaturated thioates.The stereochemistry of the reaction is discussed and compared with Knoevenagel's, Pinner's and Wittig-Horner's reactions.
Studies on Organophosphorus Compounds. XXXVIII. Synthesis of 2,3-Unsaturated O-Alkyl Thioesters, 2,3-Unsaturated Thioamides and Tetrahydro-2H-1,3,2-thiazaphosphorin-4-one 2-Sulfides
Scheibye, S.,Lawesson, S.-O.,Roemming, C.
, p. 239 - 246 (2007/10/02)
Ethyl 2-butenoate (ethyl crotonate), ethyl 3-phenyl-2-propenoate (ethyl cinnamate), methyl2-cyano-3-phenyl-2-propenoate, and ethyl 2-cyano-3,3-diphenyl-2-propenoate, react with 2,4-bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane 2,4-disulfide, 1, at 140 deg C in xylene under formation of the corresponding O-alkyl thioesters.N-Unsubstituted, N-substituted, and N,N-disubstituted 3-phenyl-2-propenamides (cinnamamides) as well as N,N-disubstituted 2-butenamides (crotonamides) give the corresponding thioamides when treated with 1 in toluene at 60 deg C. 2-Propenamide, 2-butenamide, and 3-methyl-2-butenamide give, however, 2H-1,3,2-thiazaphosphorin-4-ones, 10-12, after recation with 1 in HMPA at 60 deg C.The 6-methyl derivative, 11, was separated in the cis and trans forms and spectroscopic data of these isomers and X-ray crystallographic data of trans-11 are given.The 2H-1,3,2-thiazaphosphorin-4-one, 10, is readily transformed into the corresponding 4-thione by reaction with 1 at 90 deg C in toluene.
Thiono and Dithio Esters, XXII. α,β-Unsaturated Thiono and Dithio Esters
Hoffmann, Rainer,Hartke, Klaus
, p. 919 - 933 (2007/10/02)
α,β-Unsaturated thiono and dithio esters such as O-ethyl thiocinnamate (3), methyl dithiocinnamate (7), O-ethyl thiocrotonate (17), and O,O-diethyl dithiofumarate (28) have been prepared by thiolysis between 20 and - 75 deg C from the corresponding O- or S-alkylated tertiary amides or thioamides.They tend to dimerize in part by cycloadditions.Methyl dithiocrotonate (24) could only be isolated as the endo-dimer 25.
