- Preparation of Thiazole-2-thiones through TBPB-Promoted Oxidative Cascade Cyclization of Enaminones with Elemental Sulfur
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An unprecedented method for the construction of thiazole-2-thiones via an oxidative cascade cyclization strategy is described. The novel protocol involves the simultaneous formation of two C - S bonds and a C═S bond on the structure of enaminones in a single operation through a cascade of C(sp2) - H/C(sp3) - H bond sulfurations and C(sp3)-H bond thiocarbonylation. This transformation allows for the efficient synthesis of thiazole-2-thiones with broad tolerance in moderate to excellent yields from simple enaminones with elemental sulfur.
- Zhang, Biao,Liu, Donghan,Sun, Yulin,Zhang, Yajing,Feng, Jiayi,Yu, Fuchao
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Read Online
- A Mild Heteroatom (O -, N -, and S -) Methylation Protocol Using Trimethyl Phosphate (TMP)-Ca(OH) 2Combination
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A mild heteroatom methylation protocol using trimethyl phosphate (TMP)-Ca(OH)2combination has been developed, which proceeds in DMF, or water, or under neat conditions, at 80 °C or at room temperature. A series of O-, N-, and S-nucleophiles, including phenols, sulfonamides, N-heterocycles, such as 9H-carbazole, indole derivatives, and 1,8-naphthalimide, and aryl/alkyl thiols, are suitable substrates for this protocol. The high efficiency, operational simplicity, scalability, cost-efficiency, and environmentally friendly nature of this protocol make it an attractive alternative to the conventional base-promoted heteroatom methylation procedures.
- Tang, Yu,Yu, Biao
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- Cleaner and greener synthesis of 3H-benzothiazole-2-thione and its derivatives
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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.
- Srivastava, Nitin,Kishore, Ram
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- 3 - Methyl -2 - benzothiazolinone hydrazone hydrochloride salt and its hydrate synthesis method
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The present invention provides 3 - methyl - 2 - benzothiazolinone hydrazone hydrochloride salt and its hydrate synthesis method, which belongs to the field of organic synthesis. N - methylaniline with carbon disulfide reaction to obtain N - methyl - N - phenyl dithio-, then reaction with bromine 3 - methylbenzothiazol - 2 - thione, then reacting with hydrazine hydrate to produce 3 - methyl - 2 - benzothiazolinone hydrazone, subsequently react with hydrochloric acid to obtain 3 - methyl - 2 - benzothiazolinone hydrazone hydrochloride, recrystallization to obtain water in 3 - methyl - 2 - benzothiazolinone hydrazone hydrochloride hydrate. In the present invention the used raw materials are cheap and easily obtained, the operation process is simple, and has potential industrial amplifying application prospect.
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Paragraph 0016; 0017; 0018
(2019/01/08)
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- A catalyst-free and additive-free method for the synthesis of benzothiazolethiones from: O -iodoanilines, DMSO and potassium sulfide
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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.
- Zhu, Xiaoming,Li, Wenguang,Luo, Xiai,Deng, Guobo,Liang, Yun,Liu, Jianbing
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p. 1970 - 1974
(2018/05/23)
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- Copper-Catalyzed Three-Component Synthesis of Benzothiazolethiones from o-Iodoanilines, Isocyanide, and Potassium Sulfide
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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.
- Dang, Pan,Zeng, Weilan,Liang, Yun
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supporting information
p. 34 - 37
(2015/07/28)
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- A convenient metal-free method for the synthesis of benzothiazolethiones from o-haloanilines and carbon disulfide
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A convenient method has been developed for the preparation of a variety of 1,3-benzothiazole-2(3H)-thiones. The reaction proceeds from an o-haloaniline derivative and carbon disulfide in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene at 80-140 °C to g
- Wang, Fei,Xi, Chanjuan,Zhao, Peng
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p. 1477 - 1480
(2020/01/03)
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- Ionic liquids - Promoted S-methylation of thiols utilizing dimethyl carbonate
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Convenient and efficient S-methylation of mercaptans or thiophenols occurs with dimethyl carbonate (DMC) in room temperature ionic liquids (RTILs) [Bmim]Cl. [Bmim]Cl can be recycled in four subsequent runs with only a gradual decrease in activity. A possible mechanism of this transformation is also discussed. Supplemental materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements to view the free supplemental file. Copyright Taylor & Francis Group, LLC.
- Xie, Jiangang,Wu, Chengyao,Christopher, Branford White,Quan, Jing,Zhu, Limin
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experimental part
p. 31 - 37
(2011/04/22)
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- SH-methylation of SH-containing heterocycles with dimethyl carbonate via phase-transfer catalytic reaction
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A reaction of SH-containing heterocycles with dimethyl carbonate (DMC) in the presence of K2CO3 and tetrabutylammonium bromide (Bu4NBr) gave heteroaryl methyl thioethers in 44-93% yields. The reaction was carried out under mild conditions. This method provided a useful synthetic method for preparation of various heteroaryl methyl thioethers without the use of toxic methylic halides or dimethyl sulfate.
- Xie, Jian-Gang,Quan, Jing,Li, Shu-Bai,Zheng, Yan,Zhu, Li-Min
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experimental part
p. 871 - 878
(2011/04/22)
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- REACTION OF (2-BENZOTHIAZOLYL)-SULFENAMIDES WITH P-CONTAINING REAGENTS
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The title reaction was investigated to find that only substitution reaction on amino group occured when (2-benzothiazoly)sulfenamides 1 reacted with P(NR2)3, whereas the treatment of 1 with (RO)P(NR2)2 gave derivatives of phosphorodiamidothioic acid together with 2-alkylthiobenzothiazole and its isomer in addition to substitution products, and no substitution products obtained when N-substituted analogues of 1 were treated similarly.
- Zhang, Jing-Lin,Ma, Xiao-Bo
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- An Unusual S- and N-Alkylation of Mercapto Substituted Heterocycles with O,O-Dialkyl Chlorophosphate/Thiophosphate
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The reaction of different mercapto substituted heterocycles with O,O-dialkyl chlorophosphate or thiophosphates, gave the corresponding S- and N- alkylated derivatives instead of the expected phosphorylated products.
- Rani, B. Radha,Bhalerao, U.T.,Rahman, M.F.
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p. 3045 - 3052
(2007/10/02)
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- Dication Ethers and Related Compounds, 1. On Dication Chalkogenides and Dichalkogenides
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Reaction of N,N-, N,S-, S,S-, and O,O-substituted thiones 4a-f or selones 6a-c with trifluoromethanesulfonic anhydride leads to dication disulfides 5a-f or diselenides 7a-c, resp.No dication sulfides or selenides are obtained whose formation would parallel the reactivity of the corresponding urea derivatives.This class of dications (14, 15) is, on the other hand, accessible by the reaction of dication ethers 13 with thiones 4 or selones 6. 1H and 13C NMR data of the dication dichalkogenides and chalkogenides are compared with each other.
- Maas, Gerhard,Singer, Berndt
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p. 3659 - 3674
(2007/10/02)
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