- The Willgerodt-Kindler reaction in water: High chemoselectivity of benzaldehydes over acetophenones
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Water has been found for the first time as a useful solvent in the Willgerodt-Kindler (WK) reaction for the synthesis of benzothiomorpholides in high yield at 80°C for 3 h. This novel approach confronts the WK protocol with a new situation in which water
- Aghapoor, Kioumars,Mohsenzadeh, Farshid,Khanalizadeh, Golriz,Darabi, Hossein R.
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Read Online
- Microwave-Assisted Conversion of Nitriles to Thioamides in Solvent-Free Condition
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Nitriles are efficiently transformed to thiomorpholides via the Willgerodt-Kindler reaction under microwave irradiation in solvent-free conditions.
- Moghaddam, Firouz Matloubi,Hojabri, Leila,Dohendou, Mohammad
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Read Online
- 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 0053-0055
(2021/03/31)
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- Mixed bases mediated synthesis of thioamides in water
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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
- Li, Jiao,Ren, Xuanhe,Li, Ganzhong,Liang, Helong,Zhao, Yajie,Wang, Zhiwu,Li, Heng,Yuan, Bingxin
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p. 229 - 237
(2020/02/20)
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- Structure–activity relationships (SARs) of α- ketothioamides as inhibitors of phosphoglycerate dehydrogenase (PHGDH)
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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.
- Spillier, Quentin,Ravez, Séverine,Unterlass, Judith,Corbet, Cyril,Degavre, Charline,Feron, Olivier,Frédérick, Rapha?l
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- Graphene Oxide: A Metal-Free Carbocatalyst for the Synthesis of Diverse Amides under Solvent-Free Conditions
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An environmentally friendly, inexpensive, carbocatalyst, graphene oxide (GO) promoted efficient, metal-free transamidation of various carboxamides with aliphatic, cyclic, and aromatic amines is demonstrated. The protocol is equally applicable to phthalimide, urea, and thioamide determining its adaptability. The oxygenated functionalities such as carbonyl (?C=O), epoxy (?O?), carboxyl (?COOH) and hydroxyl (?OH), present on graphene oxide surface impart acidic properties to the catalyst. The graphene oxide being heterogeneous in nature, work efficiently under solvent-free reaction conditions providing desired products in good to excellent yields. The one-pot synthesis of 2,3-Dihydro-5H-benzo[b]-1,4-thiazepin-4-one moiety by GO catalyzed Aza Michael addition followed by intramolecular transamidation is also described. A plausible reaction mechanistic pathway involving H-bonding is discussed. The graphene oxide can be recycled and reused up to five cycles without much loss in catalytic activity. (Figure presented.).
- Patel, Khushbu P.,Gayakwad, Eknath M.,Patil, Vilas V.,Shankarling, Ganapati S.
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supporting information
p. 2107 - 2116
(2019/03/26)
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- Willgerodt-Kindler reaction at room temperature: Synthesis of thioamides from aromatic aldehydes and cyclic secondary amines
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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,
- Kale, Arun D.,Tayade, Yogesh A.,Mahale, Sachin D.,Patil, Rahul D.,Dalal, Dipak S.
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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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- 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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- An Efficient Heterobimetallic Lanthanide Alkoxide Catalyst for Transamidation of Amides under Solvent-Free Conditions
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A practical heterobimetallic lanthanide-catalyzed transamidation of primary, secondary and tertiary amides with aliphatic and aromatic amines has been developed. The methodology was also applied to the weakly reactive thioamides to demonstrate its versatility and wide substrate scope. The heterobimetallic lanthanide catalysts showed high catalytic activity and a wide scope of substrates with good to excellent yields under solvent-free conditions. Efficient activation of the transamidation can be realized by the above complexes acting as cooperative acid–base bifunctional catalysts, which are proposed to be responsible for the higher reactivity in comparison with simple monometallic catalysts. (Figure presented.).
- Sheng, Hongting,Zeng, Ruijie,Wang, Wenjuan,Luo, Shuwen,Feng, Yan,Liu, Jing,Chen, Weijian,Zhu, Manzhou,Guo, Qingxiang
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p. 302 - 313
(2017/02/05)
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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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- Kinetic study on aminolysis of 4-pyridyl benzoate and O-4-pyridyl thionobenzoate in acetonitrile: Factors influencing reactivity and reaction mechanism
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A kinetic study on nucleophilic substitution reactions of 4-pyridyl benzoate (2a) andO-4-pyridyl thionobenzoate (2b) with a series of cyclic secondary amines in acetonitrile at 25.0°C is reported. Plots of pseudo-first-order rate constant (kobsd) vs. [amine] are linear and pass through the origin for the reactions of 2a but curve upward for those of 2b. The upward curvature observed for the reactions of 2b is typical for reactions that proceed through a stepwise mechanism with a zwitterionic intermediate T±, which decomposes to the products via uncatalyzed and catalyzed routes competitively. The reaction of 2a has been suggested to proceed through a stepwise mechanism with T±, in which expulsion of the leaving group occurs in the rate-determining step on the basis of a linear Br?nsted-type plot with βnuc = 0.77. The catalyzed reaction of 2b from T± has been proposed to proceed through a concerted mechanism with a six-membered cyclic transition state rather than via a stepwise pathway with an anionic intermediate T-. Factors influencing reactivity and reaction mechanism are discussed in detail.
- Um, Ik-Hwan,Kim, Min-Young,Lee, Jae-In
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p. 1577 - 1581
(2016/10/13)
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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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- H-β-zeolite catalyzed transamidation of carboxamides, phthalimide, formamides and thioamides with amines under neat conditions
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Efficient transamidation of unactivated carboxamides, phthalimides, formamides and thioamides with amines under solvent-free conditions using H-β-zeolite as a green and recyclable heterogeneous catalyst is described. Easy work up, high purity of the products, recyclability and environmentally-friendly nature of the catalyst are the attractive features of the present methodology. This is the first report for the transamidation of thioamides under heterogeneous conditions.
- Rao, Sadu Nageswara,Chandra Mohan, Darapaneni,Adimurthy, Subbarayappa
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p. 95313 - 95317
(2015/11/24)
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- Decarboxylative thioamidation of arylacetic and cinnamic acids: A new approach to thioamides
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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.
- Guntreddi, Tirumaleswararao,Vanjari, Rajeshwer,Singh, Krishna Nand
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supporting information
p. 3624 - 3627
(2014/08/05)
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- Direct conversion of methylarenes into dithiocarbamates, thioamides and benzyl esters
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A new strategy for the synthesis of a variety of dithiocarbamates and thioamides has been developed employing inexpensive and readily available methylarenes under metal-free and solvent-free conditions. The approach offers a one-pot procedure and has also been extended to the synthesis of a diverse range of benzyl esters.
- Guntreddi, Tirumaleswararao,Vanjari, Rajeshwer,Singh, Krishna Nand
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p. 3887 - 3892
(2014/06/09)
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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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- Zinc chloride catalyzed ring opening of N-arylsulfonyl aziridines by thioamides: A new approach to the synthesis of amidines
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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
- Hajibabaei, Khadijeh,Zali-Boeini, Hassan
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p. 2044 - 2048
(2014/11/08)
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- Efficient and selective multicomponent oxidative coupling of two different aliphatic primary amines into thioamides by elemental sulfur
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An efficient and selective multicomponent oxidative coupling of two different aliphatic primary amines into thioamides by elemental sulfur under solvent-free conditions has been developed.
- Nguyen, Thanh Binh,Ermolenko, Ludmila,Al-Mourabit, Ali
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supporting information; experimental part
p. 4274 - 4277
(2012/09/22)
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- Sulfated tungstate: An efficient catalyst for synthesis of thioamides via Kindler reaction
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New application of sulfated tungstate, a mildly acidic solid inorganic acid, as reusable heterogeneous catalyst for efficient Kindler reaction, a three component reactions of aldehydes, amines and sulfur, for synthesis of thioamides is discussed.
- Pathare, Sagar P.,Chaudhari, Pramod S.,Akamanchi, Krishnacharya G.
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experimental part
p. 125 - 129
(2012/07/03)
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- Efficient and green protocol for the synthesis of thioamides in C 6 (mim)2Cl2 as a dicationic ionic liquid
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A simple, efficient, facile and eco-friendly process for the synthesis of thioamides from nitriles using 1,6-bis(3methylimidazolium-1-yl)hexane chloride [C6(mim)2Cl2] as a dicationic ionic liquid (DIL) was developed. The ionic liquid was easily separated from the reaction mixture and was recycled at least four times without any loss of its activity.
- Khosropour,Noei,Mirjafari
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experimental part
p. 752 - 758
(2010/11/04)
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- Efficient one-step synthesis of benzazoles in aqueous media
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Benzazoles (benzoxazoles, benzothiazoles, and benzimidazoles) were efficiently prepared by the aquatic reaction of the corresponding thioamidinium salts and 2-aminophenol, 2-aminothiophenol, and 1,2-diaminobenzene, respectively. The thioamidinium salt was successfully applied as an alternative to a carboxylic acid derivative to react smoothly with an amino precursor and in the presence of catalytic amounts of hexadecyltrimethylammonium bromide salt to produce benzazoles in good to excellent yields. Wiley-VCH Verlag GmbH & Co. KGaA 2009.
- Boeini, Hassan Zali,Najafabadi, Khadijeh Hajibabaei
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supporting information; experimental part
p. 4926 - 4929
(2010/01/18)
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- Highly efficient synthesis of thioesters in water
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Thioesters were efficiently prepared via the direct reaction of tertiary thioamides and alkyl halides in water, and in the presence of catalytic amounts of NaI, hexadecyltrimethylammonium bromide (HTAB), and 1,4-diazabicyclo[2.2.2] octane (DABCO). Hence,
- Boeini, Hassan Zali,Kashan, Maryam Eshghi
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experimental part
p. 1987 - 1991
(2010/07/04)
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- Benzotriazole-assisted thioacylation
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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.
- 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.
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p. 7866 - 7881
(2007/10/03)
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- Extension of the Willgerodt-Kindler reaction: Protected carbonyl compounds as efficient substrates for this reaction
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Nitrogen derivatives of carbonyl compounds such as oximes, hydrazones, and semicarbazones were found to be excellent candidates for the Willgerodt-Kindler reaction. They can be used directly in a solvent-free reaction, under both classical and microwave conditions, to give the corresponding thiomorpholides in good yields.
- Darabi, Hossein Reza,Aghapoor, Kioumars,Tajbakhsh, Mahmoud
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p. 4167 - 4169
(2007/10/03)
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- Willgerodt-kindler's microwave-enhanced synthesis of thioamide derivatives
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The Willgerodt-Kindler reaction was applied to a series of aromatic aldehydes and ketones. The reactions were performed in a dipolar aprotic solvent (mainly DMF) in the presence of a base catalyst (4-methylmorpholine) and utilized microwave (mw) irradiation. The pulsed mw technique rather than the continuous irradiation was preferred because it limited side reactions and hydrogen sulfide production. While not always superior to the thermal activation of the reaction, the procedure involving repetitive short pulses of microwave irradiation was found to be faster and result in consistently cleaner products. The technique can be easily applied in a fast parallel synthesis process.
- Poupaert, Jacques H.,Duarte, Sandro,Colacino, Evelina,Depreux, Patrick,McCurdy, Christopher R.,Lambert, Didier L.
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p. 1959 - 1973
(2007/10/03)
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- The effect of medium on rate and mechanism: Aminolysis of O-4-nitrophenyl thionobenzoate in MeCN and H2O
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Pseudo-first-order rate constants (kobs) have been measured spectrophotometrically for reactions of O-4-nitrophenyl thionobenzoate (1) with a series of alicyclic secondary amines in MeCN and H2O at 25.0 ± 0.1 °C. The plot of kobs vs amine concentration exhibits an upward curvature in all cases, indicating that the reactions proceed through two tetrahedral intermediates (a zwitterionic T ± and its deprotonated anionic T-) regardless of the amine basicity and the nature of the reaction medium. However, all the amines investigated have been found to be much less reactive in MeCN than in H2O, although the amines are more basic in the former medium by 7-9 pKa units.
- Um, Ik-Hwan,Seok, Jin-A,Kim, Han-Tae,Bae, Sun-Kun
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p. 7742 - 7746
(2007/10/03)
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- The different, but interesting behaviors of benzyl systems in the Willgerodt-Kindler reaction under solvent-free conditions
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On the benzyl system, bearing various functional groups, have been carried out the Willgerodt-Kindler reaction to obtain thiobenzmorpholide (1). The reactions, under solvent-free conditions, were performed in both classical (reflux, room temperature) and
- Aghapoor, Kioumars,Darabi, Hossein Reza,Tabar-Heydar, Kourosh
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p. 1183 - 1187
(2007/10/03)
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- Microwave-assisted rapid hydrolysis and preparation of thioamides by Willgerodt-Kindler reaction
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Aldehydes and aryl alkyl ketones were efficiently transformed to thioamides with the same number of carbon atoms via Willgerodt-Kindler reaction under microwave irradiation in solvent-free conditions. The thioamides obtained were hydrolyzed to corresponding carboxylic acids with microwave dielectric heating in one minute. Both reactions are very fast and the yields are excellent.
- Matloubi Moghaddam,Ghaffarzadeh
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p. 317 - 321
(2007/10/03)
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- Addition-Elimination Mechanism of Aminolyses of 4-Nitrophenyl Benzoate and Its Sulfur Analogue
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The aminolysis of O-(4-nitrophenyl) thiobenzoate proceeds via an addition-elimination mechanism in which the rate-determining step is dependent on both concentration and basicity of amines.
- Um, Ik-Hwan,Kwon, Hye-Jin,Kwon, Dong-Sook
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p. 1801 - 1817
(2007/10/03)
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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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- Reaction of Thioaldehydes with Amines
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The reaction of phosphonium ylides with elemental sulfur gave thioaldehydes, which changed to the corresponding thioamides in good yields when treated with amines.When thioaldehydes containing α-hydrogens were treated with secondary amines, the corresponding enamines or reduction products were obtained.
- Okuma, Kentaro,Komiya, Yasuo,Ohta, Hiroshi
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p. 2402 - 2406
(2007/10/02)
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- Non-staining and slightly-staining antiozonants
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There is disclosed compounds having, within their structural formulae, a trivalent moiety: STR1 which exhibit antiozonant activity when added to rubber compositions at antiozonant effective levels and which exhibit synergistic antiozonant activity when used with conventional antiozonants in rubber compositions. There is also disclosed novel compounds which can be used as antiozonants.
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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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- Reactions of Phosphonium Ylides with S8 or Se in the Presence of Amines. Formation of Thioaldehydes or Selenoaldehydes
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The reaction of phosphonium ylides with elemental sulfur gave thioaldehydes which were successfully changed to corresponding thioamides when treated with secondary amines.On the other hand, the reaction of selenoaldehydes with secondary amines afforded bis(dialkylamino)methanes in good yields.
- Okuma, Kentaro,Komiya, Yasuo,Ohta, Hiroshi
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p. 1145 - 1148
(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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- 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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- 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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- Infrared spectra of several thiopiperidides and thiomorpholides
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Infrared spectra in the 1700-500 cm-1 region have been studied for several types of thiopiperidides (thiobenzoylpiperidides, thiocinnamoylpiperidides and phenylthioacetpiperidides) and for the corresponding thiomorpholides.Three characteristic thioamide bands were located and assigned.The behaviour of these bands on molecular complexing (with iodine as an electron acceptor) was used to support the assignments.The experimental data were discussed in terms of the theoretical results obtained by an HMO procedure.
- Cornea, Felicia,Cercasov, Cornelia,Ciureanu, Mariana
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p. 775 - 782
(2007/10/02)
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