- Efficient Synthesis of α-Ketothioamides From α-Nitroketones, Amines or DMF and Elemental Sulfur Under Oxidant-Free Conditions
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We have developed a practical, general protocol for denitration of readily available α-nitroketones with sulfur and amines to access a broad range of α-ketothioamides under mild conditions. Such a reaction proceeds under metal-, oxidant-, and catalyst-free conditions to provide synthetically useful α-ketothioamides. Furthermore, the mild reaction conditions tolerate a wide range of substrates especially for the synthesis of aliphatic α-ketothioamides which are rarely reported.
- Zhang, Zhenlei,Yang, Jiusi,Yu, Renjie,Wu, Kairui,Bu, Jiping,Li, Shaoke,Qian, Peng,Sheng, Liangquan
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supporting information
p. 5209 - 5212
(2021/10/19)
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- Metal-Free C-N or C-C Bond Cleavages of α-Azido Ketones: An Oxidative-Amidation Strategy for the Synthesis of α-Ketothioamides and Amides
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A novel metal-free oxidative-amidation strategy for the synthesis of α-ketothioamides and amides from α-azido ketones was developed. The C-H bond thionation of α-azido ketones with elemental sulfur could form α-ketothioacyl azide, which was then nucleophilically attacked by amines, causing the cleavage of the C-N bond to afford α-ketothioamides, while amides could be formed with the release of nitrogen gas and cyano anion in the presence of PhI(OAc)2 by selective C-C bond cleavage.
- Yu, Pei,Wang, Yuwei,Zeng, Zhigang,Chen, Yunfeng
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p. 14883 - 14891
(2019/11/11)
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- Methyl ketone break-and-rebuild: A strategy for full α-heterofunctionalization of acetophenones
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The Willgerodt reaction under iron-catalyzed aerobic conditions was found to be an excellent tool for full α-heterofunctionalization of acetophenones with sulfur and amines. Via this break-and rebuild strategy, a wide range of thioglyoxamides was synthesi
- Nguyen, Thanh Binh,Retailleau, Pascal
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supporting information
p. 5371 - 5374
(2017/11/22)
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- Direct synthesis of α-ketothioamides from aryl methyl ketones and amines via I2-promoted sp3 C-H functionalization
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A domino reaction that involves the formation of CS and C-N bonds in one process via sp3 C-H functionalization strategy has been developed. This reaction affords an efficient and direct method for the synthesis of α-ketothioamides from aryl met
- Li, Hong-Zheng,Xue, Wei-Jian,Wu, An-Xin
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p. 4645 - 4651
(2014/06/23)
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- Reactions of diphenacylaniline and diphenacyl sulfide under Gewald conditions: Generation of enamines and thioamides
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The 1,5-diketone, diphenacylaniline, yielded an enamine under Gewald conditions, while another 1,5-diketone, diphenacyl sulfide, resulted in thioamide formation under identical conditions. 2-Amino-4-(3-oxo-1,3- diphenylpropyl)-4,5,6,7-tetrahydrobenzo[b]th
- Paul, Nidhin,Sathishkumar, Ramalingam,Anuba, Chellathurai,Muthusubramanian, Shanmugam
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p. 7445 - 7451
(2013/06/27)
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- A facile aerobic copper-catalyzed α-oxygenation of aryl thioacetamides: An efficient access to α-keto aryl thioamides
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Copper(II) efficiently catalyzes the aerobic oxidation of aryl thioacetamides into the corresponding α-keto aryl thioamides in moderate to high yields in the presence of K2CO3 under O 2 atmosphere. This protocol is simple, clean, and generates water as the only byproduct. A mechanism is proposed for the reaction course. Georg Thieme Verlag Stuttgart.
- Moghaddam, Firouz Matloubi,Mirjafary, Zohreh,Saeidian, Hamdollah,Javan, Marjan Jebeli
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p. 892 - 896
(2008/12/22)
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