- Cobalt(iii)-catalyzed C-H amidation of: N, N -dialkyl thiobenzamides by sulfur coordination
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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
- Gao, Pengpeng,Zhang, Xiaohui,Zheng, Qing-Zhong
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supporting information
p. 10332 - 10336
(2021/12/17)
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- Ruthenium(II)-catalyzed C-H arylation of N,N-dialkyl thiobenzamides with boronic acids by sulfur coordination in 2-MeTHF
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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.
- Zhang, Jin,Liu, Ying,Jia, Qiangqiang,Wang, Yue,Ma, Yangmin,Szostak, Michal
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supporting information
p. 6884 - 6890
(2020/09/15)
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- PHOTOCATALYTIC SYSTEM AND APPLICATIONS THEREOF
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The present invention relates to novel poly(heptazine imides), a photocatalytic system comprising such poly(heptazine imides) and a sulfur source as well as the application thereof in photocatalytic reactions.
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Page/Page column 35; 36
(2019/05/15)
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- Microwave-Assisted iodine-catalyzed oxidative coupling of dibenzyl(difurfuryl)disulfides with amines: A rapid and efficient protocol for thioamides
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An efficient protocol for synthesis of thioamides was developed via the microwave-Assisted iodine-catalyzed oxidative coupling of dibenzyl(difurfuryl)disulfides with amines. This process is scalable and tolerates a wide spectrum of amines to deliver the corresponding products in moderate to excellent yields in 10 minutes, providing a cheap and rapid approach to thioamides.
- Chen, Jinyang,Mei, Lan,Liu, Jialing,Zhong, Chuntao,Yuan, Binfang,Li, Qiang
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p. 28576 - 28580
(2019/09/30)
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- Sulfur-Catalyzed Oxidative Coupling of Dibenzyl Disulfides with Amines: Access to Thioamides and Aza Heterocycles
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In the presence of catalytic amounts of elemental sulfur, dibenzyl disulfide/DMSO was found to be an excellent thiobenzoylating agent of amines to provide a wide range of thioamides. The reaction becomes autocatalytic when anilines substituted by an o-cyclizable group were used as nucleophile, leading to the corresponding 2-aryl aza heterocycles. (Figure presented.).
- Nguyen, Thanh Binh,Nguyen, Le Phuong Anh,Nguyen, Thi Thu Tram
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supporting information
p. 1787 - 1791
(2019/02/26)
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- Oxidative Coupling-Thionation of Amines Mediated by Iron-Based Imidazolium Salts for the Preparation of Thioamides
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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.
- Gisbert, Patricia,Pastor, Isidro M.
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supporting information
p. 3031 - 3040
(2018/07/06)
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- Carbon nitride creates thioamides in high yields by the photocatalytic Kindler reaction
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Potassium poly(heptazine imide), a carbon nitride based photocatalyst, effectively promotes the Kindler reaction of thioamide bond formation using amines and elemental sulfur as building blocks under visible light irradiation. The feasibility of the developed methodology was confirmed using 14 different primary and secondary amines, including substituted benzylamines and heterocyclic and aliphatic methylamines, which were successfully converted into thioamides with 68-92% isolated yields.
- Kurpil,Kumru,Heil,Antonietti,Savateev
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supporting information
p. 838 - 842
(2018/03/05)
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- Sulfated polyborate catalyzed Kindler reaction: a rapid, efficient, and green protocol
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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.].
- Khatri, Chetan K.,Mali, Anil S.,Chaturbhuj, Ganesh U.
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p. 1463 - 1468
(2017/07/18)
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- Iodine-Promoted Synthesis of Thioamides from 1,2-Dibenzylsulfane and Difurfuryl Disulfide
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Thioamides can be generated at 100 °C in high yield through the reaction of 1,2-dibenzyldisulfane with difurfuryldisulfide using iodine as oxidant and DMSO as solvent. The protocol is metal- and additive-free, providing a convenient and economical way for the synthesis of various kinds of thioamides under mild conditions.
- Chen, Sihai,Li, You,Chen, Jinyang,Xu, Xinhua,Su, Lebin,Tang, Zhi,Au, Chak-Tong,Qiu, Renhua
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supporting information
p. 2339 - 2344
(2016/09/28)
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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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- Selective thioacylation of amines in water: A convenient preparation of secondary thioamides and thiazolines
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Primary thioamides have been utilised directly in water, without any derivatisation, to selectively thioacylate primary amines. By employing 2-hydroxyethylamines, the reaction can be extended to the preparation of 2-thiazolines via formation of β-hydroxythioamides.
- Pathak, Uma,Bhattacharyya, Shubhankar,Mathur, Sweta
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p. 4484 - 4488
(2015/02/19)
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- Thiol as a synthon for preparing thiocarbonyl: Aerobic oxidation of thiols for the synthesis of thioamides
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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.
- Wang, Xi,Ji, Miran,Lim, Seungyeon,Jang, Hye-Young
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p. 7256 - 7260
(2014/08/18)
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- Nonplanar structures of thioamides derived from 7-azabicyclo[2.2.1]heptane. Electronically tunable planarity of thioamides
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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
- Hori, Tetsuharu,Otani, Yuko,Kawahata, Masatoshi,Yamaguchi, Kentaro,Ohwada, Tomohiko
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scheme or table
p. 9102 - 9108
(2009/04/11)
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- A new efficient synthesis of α-methyl-β-ketoesters through an Eschenmoser sulfide reaction
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Various α-methyl-β-ketoesters were readily synthesized through Eschenmoser condensation of thioamides with a commercially available bromoester. β-Enaminoesters were easily prepared through this sulfide contraction reaction and were hydrolysed to afford the corresponding β-ketoesters in moderate to good yields.
- Bellec, Christian,Gaurat, Olivier
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p. 1289 - 1293
(2007/10/03)
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- Synthesis of oxazines and thiazines by cyclodehydration of hydroxy amides and thioamides
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Dihydro-1,3-oxazines and -thiazines were obtained by cyclodehydration of hydroxy amides and thioamides with PEG-linked Burgess reagent or under Mitsunobu conditions. Yields were generally higher with polymer-Burgess reagent, but both conditions failed to
- Wipf, Peter,Hayes, Gregory B.
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p. 6987 - 6998
(2007/10/03)
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- A Facile Conversion of Amides and Lactams to Thioamides and Thiolactams using Tetrathiomolybdate
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Chloro iminium salts generated in situ from amides and lactams using (COCl)2 or POCl3 reacted very readily with the new sulfur transfer reagent, benzyltriethylammonium tetrathiomolybdate to afford the corresponding thioamides and thiolactams in excellent yields under mild reaction conditions.
- Ilankumaran, Palanichamy,Ramesha, A. R.,Chandrasekaran, Srinivasan
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p. 8311 - 8314
(2007/10/02)
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- Conversion of Amides and Lactams to Thioamides and Thiolactams Using Hexamethyldisilathiane
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Amides and lactams were converted to their corresponding thioamides and thiolactams employing a new protocol using hexamethyldisilathiane (TMS2S).Oxophilic promoters were employed to generate Vilsmeier-type intermediates, the most efficient reagents being phosphorus oxychloride, triphosgene, and oxalyl chloride.Thionation of intermediate chloro iminium ions was accomplished in situ with TMS2S.Yields were good to excellent for secondary and tertiary amides and lactams while yields for primary systems were poor.
- Smith, D. C.,Lee, S. W.,Fuchs, P. L.
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p. 348 - 354
(2007/10/02)
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- The reaction of α-amino-substituted diphenylphosphine oxide anions with elemental sulfur and selenium. A new route to thio- and selenoamides
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The lithiated anions of α-amino-substituted diphenylphosphine oxides 1, in which R can be hydrogen, aryl, alkyl and alkenyl, react with two equivalents of sulfur or selenium to form thio- and selenoamides, which can be isolated in good to excellent yields
- Otten, P. A.,Gen, A. van der
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p. 499 - 506
(2007/10/02)
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- Reactions of Phosphonate Carbanions with Selenium or Sulfur in the Presence of Amines. Synthesis of Seleno- and Thioamides
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The reaction of phosphonate carbanions with elemental selenium in the presence of amines afforded the corresponding selenoamides in moderate yields.The reaction of these anions with sulfur also gave thioamides.These reactions might proceed through thio- or selenoaldehyde intermediates.
- Okuma, Kentaro,Ikari, Koumei,Ohta, Hiroshi
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p. 131 - 134
(2007/10/02)
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- Synthesis of thiobenzamides by a Willgerodt-Kindler type reaction using benzyl chlorides and secondary amines
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Benzyl chlorides, variously substituted at p-position react with secondary amine and sulphur under relatively mild conditions to afford N,N-disubstituted thiobenzamides in moderate to good yields.
- Bhattacharya, Pranab K.,Bandyopadhyay, Soumitra,Pakrashi, Satyesch
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p. 673 - 674
(2007/10/02)
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- X=Y-ZH SYSTEMS AS POTENTIAL 1,3-DIPOLES. PART 20. DECARBOXYLATION OF α-IMINO ACIDS. MECHANIZM AND APPLICATIONS TO THIOAMIDE SYNTHESIS
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α-Imino acids, prepared from α-keto acids and primary amines, undergo facile decarboxylation to the corresponding imines on heating at =80 deg C in benzene or methylene chloride.Decarboxylation proceeds via a 1,2-ylide which can be trapped by sulphur to give the corresponding secondary thioamides in good yield. 1,2-Ylides from secondary amines and α-keto acids can be generated in situ and trapped with sulphur to give tertiary thioamides in excellent yield.
- Aly, Moustafa F.,Grigg, Ronald
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p. 7271 - 7282
(2007/10/02)
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- Ready Decarboxylation of Imines of α-Keto Acids. Mechanism and Application to Thioamide Synthesis
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α-Keto acids are readily decarboxylated via imine formation with primary and/or secondary amines even when imine-enamine isomerisation can occur; the process is thought to involve an intermediate zwitterion which can be trapped by sulphur to give thioamides in excellent yield.
- Aly, Moustafa F.,Grigg, Ronald
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p. 1523 - 1524
(2007/10/02)
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- The Triethylamine Catalyzed Reaction of N,N-Disubstituted Thioamide-Bromine Adducts With Unsubstituted Thiobenzamide
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The reaction of N,N-disubstituted thioamide-bromine adducts with unsubstituted thioamide, followed by treatment with triethylamine, affords novel N'-thiobenzoylamidines along with smaller amounts of secondary products.A mechanism is proposed for the formation of the amidines.The results give an insight into the initial steps of the mechanism by which thioamides are converted into 1,2,4-thiadiazoles.
- Corsaro, Antonino,Compagnini, Anna,Perrini, Giancarlo,Purrello, Giovanni
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p. 897 - 900
(2007/10/02)
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- Versatile β-Keto Ester and β-Keto Nitrile Synthesis through Sulfide Contraction.
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A versatile and efficient synthesis for various β-keto esters, including those which are α substituted, is described.The α-thio iminium salt prepared from a thioamide and a primary or secondary alkylating agent is subjected to sulfur extrusion upon addition of base and a phosphine thiophile, and the result is an enamino ester which may be hydrolyzed to the desired β-keto ester.The method is also applicable to the preparation of various substituted β-keto nitriles.
- Shiosaki, Kazumi,Fels, Gregor,Rapoport, Henry
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p. 3230 - 3234
(2007/10/02)
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