181970-94-5Relevant academic research and scientific papers
Cobalt(iii)-catalyzed C-H amidation of: N, N -dialkyl thiobenzamides by sulfur coordination
Gao, Pengpeng,Zhang, Xiaohui,Zheng, Qing-Zhong
, p. 10332 - 10336 (2021/12/17)
An efficient inexpensive cobalt(iii)-catalyzed intermolecular amidation of N,N-dialkyl thiobenzamides with 1,4,2-dioxazol-5-ones via C-H bond activation is described. The reaction proceeds with high functional group tolerance under external oxidant free conditions, providing a straightforward approach for the direct modification of thioamide derivatives, which are prevalent organic motifs found in vital biological and pharmaceutical molecules. This journal is
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.
Ruthenium(II)-catalyzed C-H arylation of N,N-dialkyl thiobenzamides with boronic acids by sulfur coordination in 2-MeTHF
Zhang, Jin,Liu, Ying,Jia, Qiangqiang,Wang, Yue,Ma, Yangmin,Szostak, Michal
, p. 6884 - 6890 (2020/09/15)
We report ruthenium(II)-catalyzed ortho-C-H arylation of N,N-dialkylthiobenzamides with boronic acids. The method employs [RuCl2(p-cym)]2 in the presence of Cu(OTf)2 and Ag2O oxidant. The reaction represents the first example of Ru-catalyzed C-H arylation directed by sulfur-containing groups and a rare example of C-H arylation directed by the versatile thiobenzamide moiety. As a further advantage, the method is performed in sustainable and eco-friendly 2-MeTHF as a solvent.
Group 13 metal carbochalcogenoato complexes: Synthesis, X-ray structure analysis, and reactions
Nakata, Norio,Kato, Shinzi,Niyomura, Osamu,Ebihara, Masahiro
, (2018/11/23)
A series of alkali metal tetrakis(carbochalcogenoato)-gallates and -indates M[M′(EOCR)4](solv.) (M?=?alkali metal; M′?=?Ga, In; E?=?S, Se) and tris(carbodithioato)aluminum, -gallates and -indates M′ (SSCR)3 (M′?=?Al, Ga, In) were prepared by the reactions of alkali metal carbochalcogenate with metal trihalogenides (M′X3; M′?=?Al, Ga, In; X?=?Cl, Br) and by those of piperidinium carbodithioates or carbodithioic and carboselenoic acids with M′X3, respectively. An X-ray molecular structure analysis revealed that they have an acetone molecule as a crystal solvent. The reactions of the potassium complexes K[M′ (EOCR)4](H2O) (E?=?S, Se) with methanol and primary and secondary amines gave the corresponding methyl ester and amides in good yields, while the reactions with iodomethane and iodine gave S- and Se-methyl chalcogenoesters RCOEMe (E?=?S, Se) in good yields. Similar reactions of the tris(carbodithioato)gallates and -indates led to the corresponding O-methyl thioesters, thioamides, and S-methyl dithioesters in moderate to good yields. Oxidation of the tetrakis- and tris-derivatives with iodine afforded the corresponding diacyl dichalcogenides (RCOE)2 (E?=?S, Se) and di(carbothioyl) disulfides in quantitative yields. These reactions appeared to occur on the carbonyl or selenium atom of the tetrakis compounds and on the sulfide sulfur or thiocarbonyl carbon atom of the tris-compounds, respectively. A possible mechanism for these I2-oxidation reactions is discussed.
A new application of rhodanine as a green sulfur transferring agent for a clean functional group interconversion of amide to thioamide using reusable MCM-41 mesoporous silica
Ray, Suman,Bhaumik, Asim,Dutta, Arghya,Butcher, Ray J.,Mukhopadhyay, Chhanda
, p. 2164 - 2170 (2013/05/08)
A novel thionation protocol for amide compounds, with the system rhodanine/secondary amine has been discovered. Clean and efficient synthesis of a variety of thioamides can be achieved through this simple and convenient method using MCM-41 mesoporous silica as an acid catalyst. For this purpose we have synthesized MCM-41 silica and characterized by using an array of sophisticated analytical techniques like BET, HR TEM, EDX, XRD, 29Si MAS NMR and FTIR. This reaction is therefore a very neat example of a functional group interconversion.
Nonplanar structures of thioamides derived from 7-azabicyclo[2.2.1]heptane. Electronically tunable planarity of thioamides
Hori, Tetsuharu,Otani, Yuko,Kawahata, Masatoshi,Yamaguchi, Kentaro,Ohwada, Tomohiko
scheme or table, p. 9102 - 9108 (2009/04/11)
X-ray crystallographic analysis showed that N-thiobenzoyl-7-azabicyclo[2.2. 1]heptane displays marked nonplanarity of the thioamide (1a, α = 167.1° and |τ| = 11.2°) as compared with the corresponding monocyclic pyrrolidine thioamide (2a, α = 174.7° and |τ
Benzotriazole-assisted thioacylation
Katritzky, Alan R.,Witek, Rachel M.,Rodriguez-Garcia, Valerie,Mohapatra, Prabhu P.,Rogers, James W.,Cusido, Janet,Abdel-Fattah, Ashraf A. A.,Steel, Peter J.
, p. 7866 - 7881 (2007/10/03)
Benzotriazole reagents for thioacylation (RCSBt), thiocarbamoylation (RR'NCSBt), aryl/alkoxy-thioacylation (ROCSBt), and aryl/alkylthiothioacylation (RSCSBt) are synthesized, and their utility is assessed by syntheses of representative heteroaryl thioureas 3a-g, thioamides 15a-s, thionoesters 16a-h, thiocarbamates 17a-e, dithiocarbamates 18a-d, thiocarbonates 19a-c, and dithiocarbonates 20a-c.
