- Dimethylamine as the key intermediate generated in situ from dimethylformamide (DMF) for the synthesis of thioamides
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An improved and efficient method for the synthesis of thioamides is presented. For this transformation, dimethylamine as the key intermediate is generated in situ from dimethylformamide (DMF). All the tested substrates produced the desired products with excellent isolated yields.
- Liu, Weibing,Chen, Cui,Liu, Hailing
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- Transition-Metal-Free, General Construction of Thioamides from Chlorohydrocarbon, Amide and Elemental Sulfur
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A general method for one-pot synthesis of thioamides is developed through a three-component reaction involving chlorohydrocarbon, amide and elemental sulfur. Such a strategy does not only avoid residual transition metal in the product but also prevent the generation of C?N coupling by-product. The latter is prone to be generated when alkane halide and amine are present. With the protocol proposed in this work, both alkyl and aryl thioamides can be obtained in moderate to excellent yields with a high tolerance of various functional groups. External oxidants are not required in the reaction. In addition, the reaction mechanisms are addressed using a combination of controlling experiments and quantum chemical calculations.
- Chen, Xinzhi,Ge, Xin,Jin, Hao,Qian, Chao,Zhou, Shaodong
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supporting information
p. 3403 - 3406
(2021/06/25)
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- Metal-free three-component synthesis of thioamides from β-nitrostyrenes, amines and elemental sulfur
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A metal-free C[dbnd]C bond cleavage reaction of β-nitrostyrenes in the presence of elemental sulfur and secondary amines/amides is described. Elemental sulfur serves as both a raw material and an oxidant for C[dbnd]C bond cleavage, and secondary amines or amides are both feasible nitrogen sources. Besides mild reaction condition and simple work-up procedure, the method provided thioamides with good to excellent yields.
- Peng, Ling,Ma, Li,Ran, Ying,Chen, Yunfeng,Zeng, Zhigang
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supporting information
(2021/05/05)
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- Method for preparing aryl thioamide compound
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The invention discloses a method for preparing an aryl thioamide compound. The method comprises the following steps: under the protection of inert gas, performing stirring to react for 6-12 hours at the reaction temperature of room temperature to 60 DEG C by taking aryl methanol as a substrate, sublimed sulfur as a sulfur source, an alkali metal complex formed by combining alkali metal salt and ligand as a catalyst, alkali as an accelerant, formamide as a solvent and an amine source; and carrying out post-treatment on the reaction product to obtain the aryl thioamide compound. According to theinvention, cheap and easily available aryl methanol is used as a substrate for three-component reaction to prepare the corresponding thioamide compound; the method for preparing the aryl thioamide compound has the technical advantages of simple technological process, high yield, less pollution, safety, environmental protection, greenness, mildness and the like.
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Paragraph 0077-0079
(2021/03/31)
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- -Annulation of Azaoxyallyl Cations and Thiocarbonyls for the Assembly of Thiazolidin-4-ones
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A base-promoted, efficient [3 + 2] annulation between azaoxyallyl cations and thiocarbonyls is reported for flexible access to highly functionalized thiazolidin-4-one derivatives in good to excellent yields. An intriguing feature of this method is the met
- Jaiswal, Vandana,Mondal, Biplab,Singh, Kuldeep,Das, Dinabandhu,Saha, Jaideep
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supporting information
p. 5848 - 5852
(2019/08/26)
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- Transition-Metal-Free Cleavage of C-C Triple Bonds in Aromatic Alkynes with S8 and Amides Leading to Aryl Thioamides
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A novel transition-metal-free cleavage reaction of C-C triple bonds in aromatic alkynes with S8 and amides furnishes aryl thioamides in moderate to excellent yields. The remarkable features of this thioamidation include the metal-free cleavage of C-C triple bond, mild reaction conditions, as well as wide substrate scope that is particularly compatible with some internal aromatic alkynes and acetamides.
- Xu, Kai,Li, Ziyi,Cheng, Fangyuan,Zuo, Zhenzhen,Wang, Tao,Wang, Mincan,Liu, Lantao
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supporting information
p. 2228 - 2231
(2018/04/30)
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- K2S2O8-promoted aryl thioamides synthesis from aryl aldehydes using thiourea as the sulfur source
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Thiourea as a sulfur atom transfer reagent was applied for the synthesis of aryl thioamides through a three-component coupling reaction with aryl aldehydes and N,N-dimethylformamide (DMF) or N,N-dimethylacetamide (DMAC). The reaction could tolerate various functional groups and gave moderate to good yields of desired products under the transition-metal-free condition.
- Bian, Yongjun,Qu, Xingyu,Chen, Yongqiang,Li, Jun,Liu, Leng
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- Aqueous Compatible Protocol to Both Alkyl and Aryl Thioamide Synthesis
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An efficient aqueous synthesis of thioamides through aldehydes, sodium sulfide, and N-substituted formamides has been developed. Both alkyl and aryl aldehydes are amenable to this protocol. N-Substituted formamides are essential for this transformation. Readily available inorganic salt (sodium sulfide) serves as the sulfur source in water, which makes this method much more practical and efficient. Furthermore, the late-stage modification of bioactive molecules and derivatives through this protocol has been established.
- Wei, Jianpeng,Li, Yiming,Jiang, Xuefeng
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supporting information
p. 340 - 343
(2016/02/03)
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- Copper(II)-catalyzed reactions of dimethylformamide with phenylacetonitrile and sulfur to form N,N-dimethylthioamides
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Novel copper-catalyzed three-component reactions of phenylacetonitrile, sulfur and DMF (dimethyformamide) for the selective preparation of N,N-dimethylthiobenzamide and N,N-dimethyl-2-phenylethanethioamides in yields of up to 96% are described. Copyright
- Qu, Yanyang,Li, Zhengkai,Xiang, Haifeng,Zhou, Xiangge
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supporting information
p. 3141 - 3146
(2013/12/04)
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- The First Synthesis of Se-Methyl Carboxylic Thionoselenolesters
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Reaction of carboxylic thionoesters with dimethylaluminium methylselenolate in diethyl ether gave the corresponding Se-methyl thionoselenolesters in 87-98percent yield.
- Khalid, Mohamed,Ripoll, Jean-Louis,Vallee, Yannick
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p. 964 - 965
(2007/10/02)
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- Reactions of S-Alkyl-N,N-disubstituted Thioamide Salts. Part 4. Sulphenamidine Derivatives
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Readily available 3-(α-dialkylaminoalkylidene)-1-alkylthiotriazenes (1) with C-aryl, benzyl, or isopropyl substituents, on being stirred with copper(I) cyanide or copper powder in dichloromethane or toluene solution at room temperature or below, give sulp
- Stansfield, Frank
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p. 2933 - 2935
(2007/10/02)
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