- Metal-free three-component synthesis of thioamides from β-nitrostyrenes, amines and elemental sulfur
-
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
-
supporting information
(2021/05/05)
-
- Mixed bases mediated synthesis of thioamides in water
-
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
-
p. 229 - 237
(2020/02/20)
-
- Willgerodt-Kindler reaction at room temperature: Synthesis of thioamides from aromatic aldehydes and cyclic secondary amines
-
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.
-
-
- Transition-Metal-Free Cleavage of C-C Triple Bonds in Aromatic Alkynes with S8 and Amides Leading to Aryl Thioamides
-
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
-
supporting information
p. 2228 - 2231
(2018/04/30)
-
- Sulfated polyborate catalyzed Kindler reaction: a rapid, efficient, and green protocol
-
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.
-
p. 1463 - 1468
(2017/07/18)
-
- Decarboxylative thioamidation of arylacetic and cinnamic acids: A new approach to thioamides
-
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
-
supporting information
p. 3624 - 3627
(2014/08/05)
-
- Zinc chloride catalyzed ring opening of N-arylsulfonyl aziridines by thioamides: A new approach to the synthesis of amidines
-
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
-
p. 2044 - 2048
(2014/11/08)
-
- Direct conversion of methylarenes into dithiocarbamates, thioamides and benzyl esters
-
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
-
p. 3887 - 3892
(2014/06/09)
-
- Efficient one-step synthesis of benzazoles in aqueous media
-
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
-
supporting information; experimental part
p. 4926 - 4929
(2010/01/18)
-
- Highly efficient synthesis of thioesters in water
-
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
-
experimental part
p. 1987 - 1991
(2010/07/04)
-
- The Willgerodt-Kindler reaction in water: High chemoselectivity of benzaldehydes over acetophenones
-
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.
-
-
- Microwave-Assisted Conversion of Nitriles to Thioamides in Solvent-Free Condition
-
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
-
p. 4279 - 4284
(2007/10/03)
-
- Microwave-assisted rapid hydrolysis and preparation of thioamides by Willgerodt-Kindler reaction
-
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
-
p. 317 - 321
(2007/10/03)
-
- Carbophilic reactions of amines or methanol with thioaldehyde-S-oxides
-
Correspondence and reprints Reaction of primary aliphatic amines with 7-ethylenic thioaldehyde-S-oxides la,b affords the corresponding imines 2a,b via a carbophilic addition of amine. When treated with sodium methoxide (1 equiv) and an excess of a primary amine, some methyl sulfinates 3 or 6, bearing a benzylic or allylic chain on the sulfur, are converted into imines 4 or 7. Treatment of the methyl sulfinates 3 with methoxide anion in THF or methanol generally affords a mixture of aldehydes 9, the corresponding dimethylacetals 14, a,a'-dimethoxydisulfides 10, esters 11, thionoesters 12 and methyl a-methoxysulfinates 15, whose ratios depend on the conditions. The formation of these compounds is best explained by a deprotonationelimination of the methyl sulfinates into the corresponding thioaldehyde-S-oxides; which then undergo a carbophilic addition of methoxide anion or methanol. Several possible reaction paths from the so-formed a-methoxysulfenate anions IX are discussed for their conversion into the final compounds. unsaturated sulfinic ester / elimination / thioaldehyde-S-oxide / imine / aldehyde / a,a -dimethoxydisulflde / thionoester / methyl u-methoxysulflnate Eisevier,.
- Baudin, Jean-Bernard,Commenil, Marie-Gabrielle,Julia, Sylvestre A.,Lome, Robert,Ruel, Odile
-
p. 1127 - 1141
(2007/10/03)
-
- The reaction of α-amino-substituted diphenylphosphine oxide anions with elemental sulfur and selenium. A new route to thio- and selenoamides
-
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
-
p. 499 - 506
(2007/10/02)
-
- Reactions of Phosphonate Carbanions with Selenium or Sulfur in the Presence of Amines. Synthesis of Seleno- and Thioamides
-
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
-
p. 131 - 134
(2007/10/02)
-
- Process for preparing 5-aroyl-1,2-dihydro-3H-pyrrolo[1,2-A]pyrrole-1,1-dicarboxylates
-
5-Aroyl-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1,1-dicarboxylates of the formula STR1 are prepared from 2-halopyrroles. Hydrolysis and β-decarboxylation of these compounds affords ketorolac and related compounds.
- -
-
-
- Preparation and Some Reactions of Bis(thioacyl) Sulfides
-
Reaction of dithioic acids with dicyclohexylcarbodiimide has been found to give the corresponding bis(thioacyl) sulfides 1 in good yield, which are very useful thioacylating reagents under mild reaction conditions.Most of the aromatic thioanhydrides (1, R = aromatic) are fairly stable green crystals at room temperature, but the aliphatic ones (1, R = aliphatic) are unstable purple oils which dimerize at room temperature to give the dithietanes 5.The reactions with nucleophiles are discussed.
- Kato, Shinzi,Shibahashi, Hiroshi,Katada, Tomonori,Takagi, Takashi,Noda, Ippei,et al.
-
p. 1229 - 1244
(2007/10/02)
-