21011-44-9Relevant articles and documents
Metal-free three-component synthesis of thioamides from β-nitrostyrenes, amines and elemental sulfur
Peng, Ling,Ma, Li,Ran, Ying,Chen, Yunfeng,Zeng, Zhigang
supporting information, (2021/05/05)
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.
Structure–activity relationships (SARs) of α- ketothioamides as inhibitors of phosphoglycerate dehydrogenase (PHGDH)
Spillier, Quentin,Ravez, Séverine,Unterlass, Judith,Corbet, Cyril,Degavre, Charline,Feron, Olivier,Frédérick, Rapha?l
, (2020/02/11)
For many years now, targeting deregulation within cancer cells’ metabolism has appeared as a promising strategy for the development of more specific and efficient cancer treatments. Recently, numerous reports highlighted the crucial role of the serine synthetic pathway, and particularly of the phosphoglycerate dehydrogenase (PHGDH), the first enzyme of the pathway, to sustain cancer progression. Yet, because of very weak potencies usually in cell-based settings, the inhibitors reported so far failed to lay ground on the potential of this approach. In this paper, we report a structure–activity relationship study of a series of α-ketothioamides that we have recently identified. Interestingly, this study led to a deeper understanding of the structure–activity relationship (SAR) in this series and to the identification of new PHGDH inhibitors. The activity of the more potent compounds was confirmed by cellular thermal shift assays and in cell-based experiments. We hope that this research will eventually provide a new entry point, based on this promising chemical scaffold, for the development of therapeutic agents targeting PHGDH.
Mixed bases mediated synthesis of thioamides in water
Li, Jiao,Ren, Xuanhe,Li, Ganzhong,Liang, Helong,Zhao, Yajie,Wang, Zhiwu,Li, Heng,Yuan, Bingxin
, p. 229 - 237 (2020/02/20)
A mixed bases mediated protocol is developed to synthesize thioamides from N-aryl or N-alkylamide, aldehyde and elemental sulfur in water. This reaction requires no addition of external oxidant and avoids large excess of amides. Various functional groups
Method for promoting elemental sulfur to synthesize thioamide by mixed alkali in water phase
-
Paragraph 0045-0048, (2020/07/13)
The invention provides a method for promoting elemental sulfur to synthesize a thioamide compound by a mixed alkali in a water phase, and belongs to the field of organic synthesis. According to the method, an aldehyde compound and an amide compound are us
Willgerodt-Kindler reaction at room temperature: Synthesis of thioamides from aromatic aldehydes and cyclic secondary amines
Kale, Arun D.,Tayade, Yogesh A.,Mahale, Sachin D.,Patil, Rahul D.,Dalal, Dipak S.
, (2019/09/12)
A simple method for the synthesis of thioamide derivatives in DMSO at room temperature and at 120 °C has been developed. Total 27 compounds were prepared under both conditions via a one-pot, three component reaction between substituted aromatic aldehydes,
Oxidative Coupling-Thionation of Amines Mediated by Iron-Based Imidazolium Salts for the Preparation of Thioamides
Gisbert, Patricia,Pastor, Isidro M.
supporting information, p. 3031 - 3040 (2018/07/06)
An efficient and selective multicomponent oxidative coupling, involving the use of two different amines, sodium phosphate, and elemental sulfur have been described for the preparation of thioamides, employing microwave irradiation. The use of an iron(III)-based imidazolium salt is essential as catalyst. Indeed, the iron-based catalyst is involved in the oxidative coupling of the two amines and in the subsequent C-S bond formation. The protocol is useful for a wide variety of primary benzylamines and alkylamines, as coupling partners. Thus, various electron-rich and electron-poor substituents in the aromatic rings and also fused piperidine derivatives, are suitable starting materials in this reaction. Some of the obtained products are important synthetic intermediates for natural products.
Sulfated polyborate catalyzed Kindler reaction: a rapid, efficient, and green protocol
Khatri, Chetan K.,Mali, Anil S.,Chaturbhuj, Ganesh U.
, p. 1463 - 1468 (2017/07/18)
A rapid, green, and efficient one-pot, three-component Kindler reaction was developed using a sulfated polyborate catalyst. The method described the reaction of aldehydes, amines/ammonium acetate, and sulfur for the synthesis of thioamides using sulfated polyborate under a solvent free condition at 100?°C. The key features of the present protocol are high yields, short reaction time, easy workup, and recyclability of a catalyst which gives economical as well as ecological rewards. The present method also has an ability to tolerate a variety of functional groups. Graphical abstract: [Figure not available: see fulltext.].
Thiol as a synthon for preparing thiocarbonyl: Aerobic oxidation of thiols for the synthesis of thioamides
Wang, Xi,Ji, Miran,Lim, Seungyeon,Jang, Hye-Young
, p. 7256 - 7260 (2014/08/18)
It is a constant challenge to develop an environmentally friendly, atom-economical, and step-economical method for the preparation of thioamides. Herein, we describe an oxidation method that affords the direct conversion of thiols to thioamides without the use of exogenous sulfur reagents. This is the first instance of a successful utilization of thiols as a synthon for the preparation of thioamides under economical conditions.
Zinc chloride catalyzed ring opening of N-arylsulfonyl aziridines by thioamides: A new approach to the synthesis of amidines
Hajibabaei, Khadijeh,Zali-Boeini, Hassan
, p. 2044 - 2048 (2014/11/08)
The first zinc chloride catalyzed ring opening of N-arylsulfonyl aziridines by thioamides is described. Various thioamides were reacted with N-arylsulfonyl aziridines in the presence of a catalytic amount of dry zinc chloride to provide the corresponding
Decarboxylative thioamidation of arylacetic and cinnamic acids: A new approach to thioamides
Guntreddi, Tirumaleswararao,Vanjari, Rajeshwer,Singh, Krishna Nand
supporting information, p. 3624 - 3627 (2014/08/05)
A new decarboxylative strategy has been developed for the synthesis of thioamides via a three-component reaction involving arylacetic or cinnamic acids, amines and elemental sulfur powder, without the need of a transition metal and an external oxidant.
