81605-65-4Relevant academic research and scientific papers
Cleaner and greener synthesis of 3H-benzothiazole-2-thione and its derivatives
Srivastava, Nitin,Kishore, Ram
, p. 29 - 39 (2020/08/14)
A cleaner and greener method of synthesis of 3H-benzothiazole-2-thione is being reported in this communication. In this method, various o-iodoaniline derivatives are reacted with carbon disulfide in the presence of Cs2CO3 and tetramethyl ammonium bromide (TMAB) to give 3H-benzothiazole-2-thione and its derivatives in higher yields.
Synthesis of thiocarbamoyl fluorides and isothiocyanates using amines with CF3SO2Cl
Jiang, Lvqi,Yi, Wenbin,Wei, Jingjing,Liang, Shuaishuai
, p. 12374 - 12381 (2020/11/10)
A practical and efficient method to synthesize thiocarbamyl fluorides and isothiocyanates from amines with trifluoromethanesulfonyl chloride was developed. In the presence of the reducing agent triphenylphosphine and sodium iodide, thiocarbamyl fluorides and isothiocyanates were synthesized from secondary/primary amine in moderate to excellent yields, respectively. A broad scope of substrates and good functional group compatibility were observed.
K2S as Sulfur Source and DMSO as Carbon Source for the Synthesis of 2-Unsubstituted Benzothiazoles
Deng, Guobo,Kuang, Daizhi,Liang, Yun,Yang, Yuan,Yu, Jiangxi,Zhang, Fuxing,Zhu, Xiaoming
supporting information, p. 3789 - 3793 (2020/06/04)
We describe a three-component reaction of o-iodoanilines with K2S and DMSO that provides 2-unsubstituted benzothiazoles in moderate to good isolated yields with good functional group tolerance. Electron-rich aromatic amines and o-phenylenediamines instead of o-iodoanilines provided 2-unsubstituted benzothiazoles and 2-unsubstituted benzimidazoles with and without K2S under similar conditions. Notably, DMSO plays three vital roles: carbon source, solvent, and oxidant.
A catalyst-free and additive-free method for the synthesis of benzothiazolethiones from: O -iodoanilines, DMSO and potassium sulfide
Zhu, Xiaoming,Li, Wenguang,Luo, Xiai,Deng, Guobo,Liang, Yun,Liu, Jianbing
, p. 1970 - 1974 (2018/05/23)
Under catalyst-free and additive-free conditions, a novel, convenient, eco-friendly method for the synthesis of benzothiazolethiones has been developed. The three-component reaction of o-iodoanilines and K2S with DMSO proceeded smoothly and the corresponding benzothiazolethiones were obtained with good isolated yields. Meanwhile, this method could be used for the synthesis of thioureas from primary diamines. Furthermore, mechanism research showed that DMSO not only functioned as a carbon source, but also as a mild oxidant in this reaction.
9-Fluorenylmethyl (Fm) Disulfides: Biomimetic Precursors for Persulfides
Park, Chung-Min,Johnson, Brett A.,Duan, Jicheng,Park, Jeong-Jin,Day, Jacob J.,Gang, David,Qian, Wei-Jun,Xian, Ming
supporting information, p. 904 - 907 (2016/03/15)
The development of a functional disulfide, FmSSPy-A (Fm = 9-fluorenylmethyl; Py = pyridinyl), is reported. It can effectively convert small molecule and protein thiols (-SH) to form -S-SFm adducts under mild conditions. This method allows for a H2S-free and biomimetic protocol to generate highly reactive persulfides (in their anionic forms). The high nucleophilicity of persulfides toward a number of thiol-blocking reagents is also demonstrated. The method holds promise for further understanding the chemical biology of persulfides and S-sulfhydration.
Copper-Catalyzed Three-Component Synthesis of Benzothiazolethiones from o-Iodoanilines, Isocyanide, and Potassium Sulfide
Dang, Pan,Zeng, Weilan,Liang, Yun
supporting information, p. 34 - 37 (2015/07/28)
An efficient copper catalyzed strategy for the synthesis of a variety of benzothiazolethione derivatives has been developed. In the presence of CuCl, the three-component reaction of o-iodoanilines and K2S with p-toluenesulfonylmethyl isocyanide proceeded smoothly to obtain the corresponding benzothiazolethiones in good to excellent isolated yields. Notably, isocyanide functioned as a carbon source and K2S functioned as a sulfur source in this reaction.
Design, synthesis and biological evaluation of bivalent benzoxazolone and benzothiazolone ligands as potential anti-inflammatory/analgesic agents
Abdelazeem, Ahmed H.,Khan, Shabana I.,White, Stephen W.,Sufka, Kenneth J.,McCurdy, Christopher R.
, p. 3248 - 3259 (2015/08/03)
Abstract Benzoxazolone and benzothiazolone were used as template blocks to develop two series of dimers as anti-inflammatory and analgesic agents based on the concept of bivalent ligands. The first series (I) involved varying the carbon chain lengths extending from the piperazine core to the nitrogen atom of the dibenzo[d]oxazol-2(3H)-one or dibenzo[d]thiazol-2(3H)-one. The second series (II) was designed by changing the attachment point. All compounds were screened for their in vitro anti-inflammatory activity in terms of the inhibition of inducible nitric oxide synthase (iNOS) and nuclear factor kappa B (NF-κB). Seventeen compounds inhibited both targets. Eleven of them exhibited IC50 values below 3 μM while five compounds showed IC50 values of 1 μM or below. Most of the compounds were found to be devoid of cytotoxicity against mammalian kidney and solid tumors cell lines up to 25 μg/mL. In vivo anti-inflammatory and antinociceptive studies revealed that compounds 3j, 5t and 8b have significant anti-inflammatory and analgesic activity comparable to that of indomethacin and ketorolac, respectively.
Sulfenylation of β-Diketones Using C- H Functionalization Strategy
Varun, Begur Vasanthkumar,Gadde, Karthik,Prabhu, Kandikere Ramaiah
, p. 2944 - 2947 (2015/06/30)
Sulfenylation of β-diketones is challenging as β-diketones undergo deacylation after sulfenylation in the reaction medium. The sulfenylation of β-diketones without deacylation under metal-free conditions at ambient temperature via a cross dehydrogenative coupling (CDC) strategy is reported. The resultant products can be further manipulated to form α,α-disubstituted β-diketones and pyrazoles.
Regioselective thiolation of arenes and heteroarenes: C-H functionalization strategy for C-S bond formation
Varun, Begur Vasanthkumar,Prabhu, Kandikere Ramaiah
supporting information, p. 9655 - 9668 (2015/01/16)
A facile transition-metal-free oxidative cross-dehydrogenative coupling reaction involving selective formation of a C-S bond leading to the synthesis of arylthiobenzoxazoles, heteroarylthiobenzoxazoles, and arylthiobenzothiazoles has been described. This highly regioselective C-H functionalization reaction with electron-rich aromatic systems including heteroaromatics is achieved by reversing the reactivity of sulfur in the presence of a suitable oxidant and strong acid. (Chemical Equation Presented).
