93366-73-5Relevant academic research and scientific papers
Ag-Cu copromoted direct C2-H bond thiolation of azoles with Bunte salts as sulfur sources
Du, Xiao,Hu, Yuntao,Wang, Rui,Wei, Yingsu,Xu, Hongyan,Zhang, Ying,Zhao, Huaiqing
supporting information, p. 5899 - 5904 (2021/07/12)
A direct C2-H thiolation of azoles with Bunte salts was achieved under the combined action of copper and silver salts. This protocol could furnish various substituted 2-thioazoles in moderate to good yields. This method has a broad substrate scope and shows good functional group tolerance.
Conformational Analysis of Acyclic α-Fluoro Sulfur Motifs
Erdeljac, Nathalie,Mück-Lichtenfeld, Christian,Daniliuc, Constantin G.,Gilmour, Ryan
, p. 13704 - 13715 (2020/10/02)
Bioactive small molecules containing α-fluoro sulfur motifs [RS(O)nCH2F] are appearing with increasing frequency in the pharmaceutical and agrochemical sectors. Prominent examples include the anti-asthma drug Flovent and t
Camphorquinone: A new and efficient oxidant for the preparation of 2-thio-substituted benzothiazoles from alcohols by oxidation-reduction condensation
Pluempanupat, Wanchai,Temyarasilp, Parinthorn,Widhalm, Michael,Chavasiri, Warinthorn
, p. 418 - 430 (2014/06/10)
A convenient one-pot procedure for the preparation of various 2-thio-substituted benzothiazoles from alcohols and benzothiazole-2-thiol utilizing camphorquinone-mediated oxidation-reduction condensation is disclosed. The condensation between benzothiazole-2-thiol and alkyl diphenylphosphinites, generated in situ from alcohols and chlorodiphenylphosphine, proceeded smoothly in the presence of camphorquinone to furnish the corresponding benzothiazoles in good to moderate yields.
Copper-mediated C-H activation/C-S cross-coupling of heterocycles with thiols
Ranjit, Sadananda,Lee, Richmond,Heryadi, Dodi,Shen, Chao,Wu, Ji'En,Zhang, Pengfei,Huang, Kuo-Wei,Liu, Xiaogang
experimental part, p. 8999 - 9007 (2011/12/03)
We report the synthesis of a series of aryl- or alkyl-substituted 2-mercaptobenzothiazoles by direct thiolation of benzothiazoles with aryl or alkyl thiols via copper-mediated aerobic C-H bond activation in the presence of stoichiometric CuI, 2,2′-bipyridine and Na2CO3. We also show that the approach can be extended to thiazole, benzimidazole, and indole substrates. In addition, we present detailed mechanistic investigations on the Cu(I)-mediated direct thiolation reactions. Both computational studies and experimental results reveal that the copper-thiolate complex [(L)Cu(SR)] (L: nitrogen-based bidentate ligand such as 2,2′-bipyridine; R: aryl or alkyl group) is the first reactive intermediate responsible for the observed organic transformation. Furthermore, our computational studies suggest a stepwise reaction mechanism based on a hydrogen atom abstraction pathway, which is more energetically feasible than many other possible pathways including β-hydride elimination, single electron transfer, hydrogen atom transfer, oxidative addition/reductive elimination, and σ-bond metathesis.
Reactions of (Benzothiazol-2-ylthio)(trimethylsilyl)methane. A General Method for α-Mercaptoalkylation by Alkylation and Alkylative Desilylation
Katritzky, Alan R.,Kuzmierkiewicz, Wojciech,Aurrecoechea, Jose M.
, p. 844 - 849 (2007/10/02)
Readily available (benzothiazol-2-ylthio)(trimethylsilyl)methane (2a) provides a convenient synthon for HSCH2- and enables the general conversions RR'CO -> RR'C(OH)CH(SH)R'' and RBr -> RCH(SH)SiMe3.The lithium derivative of 2a reacts with aldehydes and ketones to give Peterson olefination products which are protected vinyl mercaptans converted into vinyl mercaptans by reaction with methyllithium.This overall conversion is RR'CO -> RR'C:CHSH.
Carbanions Derived from 2-Alkylthiobenzothiazoles. A Novel α-Lithiomethyl Mercaptan Synthon for Mercaptomethylation.
Katritzky, Alan R.,Aurrecoechea, Jose M.,Vazques de Miguel, Luis M.
, p. 769 - 774 (2007/10/02)
2-Methylthiobenzothiazole readily gives a methyl group lithio derivative which reacts cleanly with electrophiles.The products are conveniently converted into the corresponding thiols by BuLi at -78 deg C, and this sequence thus provides a convenient two-step mercaptomethylation procedure for alkyl halides, aldehydes, and ketones.
ACTIVATION OF NITROSO GROUP WITH THIOLS. A NEW TRANSFORMATION OF PRIMARY AMINES TO ORGANIC SULFIDES OR THIOLS
Ueno, Yoshio,Tanaka, Chie,Okawara, Makoto
, p. 2675 - 2678 (2007/10/02)
Aliphatic primary amines reacted with 2-mercaptobenzothiazole in the presence of t-butylnitrite at room temperature to give condensation products, 2-(alkylthio)benzothiazole.
