- A facile access to thieno[2,3-b]indoles via sulfur-mediated decarboxylative cyclization of α, β-unsaturated carboxylic acids with indoles
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An efficient synthesis of thieno[2,3-b]indoles via a one-pot three-component reaction was well established. By using inexpensive and commercial available indoles and α, β-unsaturated carboxylic acids in the presence of elemental sulfur, various functional groups were achieved in moderate to good yields.
- Zhang, Hao-Lin,Wen, Fei,Sheng, Wen-Bing,Yin, Peng,Zhang, Chun-Tao,Peng, Cai-Yun,Peng, Dong-Ming,Liao, Duan-Fang,Fu, Rong-Geng
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- 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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- The thioamidation ofgem-dibromoalkenes in an aqueous medium
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The direct integration of sulphur and amine groups with 1,1-dibromoalkenes for thioamide synthesis has been achieved in an aqueous medium. The presented green protocol emphasizes the suitability of aqueous media for the thioamidation reaction and enables greater selectivity with synthetic utility. A wide range of thioamides in moderate to excellent yields has been achieved using readily available starting materials, with the use of no organic solvents, catalysts, or additives.
- Vankar, Jigarkumar K.,Gupta, Ankush,Jadav, Jaydeepbhai P.,Nanjegowda, Shankara H.,Gururaja, Guddeangadi N.
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p. 2473 - 2480
(2021/04/02)
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- Elemental Sulfur-Promoted Benzoxazole/Benzothiazole Formation Using a C=C Double Bond as a One-Carbon Donator
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An efficient method to assemble diverse benzoxazoles/benzothiazoles in good yields was developed via oxidative cyclization with 2-aminothiophenols or 2-iodoanilines as raw materials. In this protocol, elemental sulfur was used as the effective oxidant and C atoms on the C=C double bond were introduced as a one-carbon donator.
- Chen, Xuecheng,Han, Shiqing,Hu, Liang,Liu, Yafei,Luo, Yue,Pan, Bin,Peng, Yalan,Zhang, Jun,Zhang, Yurong
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p. 14485 - 14492
(2021/11/12)
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- Three-Component Thieno[2,3-b]indole Synthesis from Indoles, Alkenes or Alkynes and Sulfur Powder under Metal-Free Conditions
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A Bronsted acid promoted three-component synthesis of substituted thieno[2,3-b]indole has been developed starting from indoles, alkenes or alkynes, and sulfur powder. N,N-Dimethylformamide plays an important role to convert the starting materials into the fused products. Various functional groups attached to substrates were well tolerated to afford the corresponding products in moderate to good yields under very simple reaction conditions. (Figure presented.).
- Li, Bin,Ni, Penghui,Huang, Huawen,Xiao, Fuhong,Deng, Guo-Jun
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supporting information
p. 4300 - 4304
(2017/10/24)
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- Solvent-controlled highly regio-selective thieno[2,3-: B] indole formation under metal-free conditions
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An efficient three-component thieno[2,3-b]indole formation method was developed under metal-free conditions. The cascade cyclization was enabled by acid-promoted annulation of indoles, ketones and sulfur powder, which enabled modular synthesis of 2-substituted and 3-substituted thieno[2,3-b]indoles with excellent regioselectivity and broad functional group tolerance. DMF solvent played an important role in the regioselectivity control.
- Ni, Penghui,Li, Bin,Huang, Huawen,Xiao, Fuhong,Deng, Guo-Jun
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supporting information
p. 5553 - 5558
(2017/12/06)
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- Sulfur promoted decarboxylative thioamidation of carboxylic acids using formamides as amine proxy
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An efficient decarboxylative thioamidation of arylacetic and cinnamic acids has been developed employing formamides as amine surrogate and sulfur as promoter. Thioamides with variant structural features are obtained under mild reaction conditions without the use of transition metal catalysts and oxidants.
- Kumar, Saurabh,Vanjari, Rajeshwer,Guntreddi, Tirumaleswararao,Singh, Krishna Nand
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p. 2012 - 2017
(2016/04/05)
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- Dimethylamine as the key intermediate generated in situ from dimethylformamide (DMF) for the synthesis of thioamides
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An improved and efficient method for the synthesis of thioamides is presented. For this transformation, dimethylamine as the key intermediate is generated in situ from dimethylformamide (DMF). All the tested substrates produced the desired products with excellent isolated yields.
- Liu, Weibing,Chen, Cui,Liu, Hailing
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supporting information
p. 1721 - 1726
(2016/04/10)
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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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- Transition-metal-free semihydrogenation of diarylalkynes: Highly stereoselective synthesis of trans -alkenes using Na2S·9H 2O
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A highly stereoselective and efficient transition-metal-free semihydrogenation of internal alkynes to E-alkenes using cheap and green water as hydrogen donor is described. The reactions are conducted under convenient conditions and provide products in good to excellent yields, with broad substrate scope, including a variety of diarylalkynes.
- Chen, Zhengwang,Luo, Miaoting,Wen, Yuelu,Luo, Guotian,Liu, Liangxian
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supporting information
p. 3020 - 3023
(2014/06/23)
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- Synthesis of thioamides via one-pot A3-coupling of alkynyl bromides, amines, and sodium sulfide
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We herein describe a novel method for the synthesis of thioamides by a three component condensation of alkynyl bromides, amines, and Na 2S·9H2O. The developed method is applicable for a wide range of amines and alkynyl bromides bearing different functional groups furnishing the corresponding products in moderate to excellent yields. The Royal Society of Chemistry.
- Sun, Yadong,Jiang, Huanfeng,Wu, Wanqing,Zeng, Wei,Li, Jianxiao
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supporting information
p. 700 - 707
(2014/01/06)
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- Copper(II)-catalyzed reactions of dimethylformamide with phenylacetonitrile and sulfur to form N,N-dimethylthioamides
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Novel copper-catalyzed three-component reactions of phenylacetonitrile, sulfur and DMF (dimethyformamide) for the selective preparation of N,N-dimethylthiobenzamide and N,N-dimethyl-2-phenylethanethioamides in yields of up to 96% are described. Copyright
- Qu, Yanyang,Li, Zhengkai,Xiang, Haifeng,Zhou, Xiangge
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supporting information
p. 3141 - 3146
(2013/12/04)
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- ZUR UMSETZUNG VON ARYLMETHYLKETONEN MIT SCHWEFEL, SEKUNDAEREN AMINEN UND SCHWEFELDIOXID
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The acetophenones 2 react with different sulfurdioxide-secondary amine adducts 1 and sulfur to yield the red-coloured zwitterionic 2-imino-dithioacetates 3.Enamines can be proved to be intermediates in this reaction.Thus enamines 5 and other derivatives such as acetophenone anil, acetophenone diethyl acetal and diphenacyl sulfide also give 3.In the absence of 1, 3a react with hydrogen sulfide to form the thioamide of phenylacetic acid 8. Key words: 2-Iminio-dithioacetates; iminium salts; zwitterionic; SO2-secondary amin adducts; Willgerodt-Kindler-reaction; enamines; heptathiocanes.
- Matschiner, Hermann,Maschmeier, Claus-Peter,Maier, Nadja,Hansen, Jens
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p. 223 - 230
(2007/10/02)
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- N,N-DIALKYLTHIOAMIDES IN THE MICHAEL ADDITION TO CONJUGATE CARBONYL COMPOUNDS, REGIOSELECTIVITY, STEREOCHEMISTRY AND MECHANISM
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The regio- and diastereoselectivity of the addition of N,N-dialkylphenylthioacetamide enolates to some conjugate carbonyl compounds are studied.The results are compared with oxoanalogs and the differences are rationalized in terms of specific behaviour of
- Viteva, Lilia,Gospodova, Tzveta,Stefanovsky, Yuri
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p. 189 - 198
(2007/10/02)
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- The First Synthesis of Se-Methyl Carboxylic Thionoselenolesters
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Reaction of carboxylic thionoesters with dimethylaluminium methylselenolate in diethyl ether gave the corresponding Se-methyl thionoselenolesters in 87-98percent yield.
- Khalid, Mohamed,Ripoll, Jean-Louis,Vallee, Yannick
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p. 964 - 965
(2007/10/02)
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- Heterocyclic Aromatic Anions with 4n + 2 ?-Electrons
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Equilibrium acidities in DMSO for several cyclic carboxamides, thiocarboxamides, esters, and sulfones that form anions possessing 4n + 2 electrons have been measured.Aromatic stabilization energies (ASEs) for these anions have been estimated by comparing
- Bordwell, Frederick G.,Fried, Herbert E.
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p. 4218 - 4223
(2007/10/02)
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- Dimethylammonium Dimethylcarbamate - A Useful Reagent for the Willgerodt-Kindler Reaction
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Dimethylammonium dimethylcarbamate (dimcarb), easily accessible from dimethylamine and carbon dioxide, is a useful reagent for the Willgerodt-Kindler synthesis of N,N-dimethylthiocarboxamides.Moreover, dimcarb displays some unusual properties, and generally behaves as a preparatively useful dimethylamine source.
- Schroth, Werner,Andersch, Joerg
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p. 202 - 204
(2007/10/02)
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- Thioketene Syntheses, VIII. - Thioketenes by Cycloreversion of 1,3-Dithiolane Derivatives
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2-Alkylidene-1,3-dithiolanes are transformed into S,S-dioxides 1 and S-ethyl- 2 or S-arylsulfonium salts 3.After deprotonation at C-5 they form in a cycloreversion thioketenes 5, which can be trapped as thioamides 17, 18.The stabilized thioketenes 5e,i-k afford 1:1 cycloadducts 24a, b, 27a-d with azomethines; in addition, thioketene 5j provides a dimer 28j, which was characterized by an X-ray structural investigation.
- Schaumann, Ernst,Scheiblich, Stefan,Wriede, Ulrich,Adiwidjaja, Gunadi
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p. 1165 - 1176
(2007/10/02)
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- NMR-Study of the Stereochemistry and Dynamic Behaviour of Thioacrylamides
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Several model thioacrylamides, Me2N-CH=C(R)-C(S)-NMe2 (R=H, Ph -2a,b) and (p)MeO-C6H4-NH-CH=C(R)-C(S)-NMe2 (R=H, Ph -3a,b) have been synthesized.The 1H-n.m.r. spectra have been taken for discussing the E/Z-isomerism of the thioacrylamides and the assignme
- Kleinpeter, E.,Tadesse, Tsegaye,Abegaz, Berhanu
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p. 120 - 126
(2007/10/02)
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- Reactions of 1-alkynyl thiocyanates with nucleophilic reagents. Synthesis of 2,4-disubstituted 1,3-thiazoles
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Reaction of 1-alkynyl thiocyanates RCC-S-CN (1) with alcohols, phenol or thiols or secondary aliphatic amines in the presence of anhydrous zinc chloride or boron trifluoride diethyl etherate gives mixtures of 2,4-disubstituted 1,3-thiazoles (2), thiocarbonyl compounds (3) (thiono esters, dithio esters or thioamides) and 2-alkylidene-1,3-dithioles (4).In all cases, the 1,3-thiazoles can be obtained in good yields if the proper reaction conditions are applied.Interaction between 1 and lithium dialkylamides LiNR'2 gives the compounds RCC-S-NR'2 (5) (attack on sulfur).With alkoxides R'O1-, the primary attack is on CN: the in termediacy alkynethiolate RCC-S1- subsequently reacts with the alkyl cyanate R'OCN to afford 1-alkynyl sulfides RCC-SR'(6)
- Jong, R.L.P. de,Meijer, J.,Sukhai, R.S.,Bradsma, L.
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p. 310 - 313
(2007/10/02)
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- UNSATURATED THIOLATES AND THEIR ANALOGS IN CYCLOADDITION REACTIONS XI. EFFECT OF SUBSTITUENTS AT THE β POSITION OF ETHENETHIOLATES ON THE DIRECTION OF REACTION WITH CARBON BISULFIDE
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1-Dialkylamino-, 1-alkylarylamino-, and 1-cycloalkylaminoethenethiolates react with carbon bisulfide in various directions, depending on the nature of the substituents at the position 2.In all cases 1,2-dithiole-3-thiones are formed.Thiolates unsubstituted at position 2 give, in addition, 5,5'-bis(dialkylamino)-, 5,5'-bis(alkylarylamino)-, and 5,5'-bis(cycloalkylamine)-1,1',2,2'-tetrathiafulvalenes.In the case of potassium 1-morpholino-2-tert-butylethenethiolate the reaction is accompanied by the elimination of a molecule of morpholine and by the formation of 4-tert-butyl-1,2-dithiole-3-thione.In the presence of a weak proton donor (acetonitrile) ethylenethiolates substituted at position 2 react normally, but the 1-piperidinoethenethiolate gives mainly N,N-pentamethylenetrithiomalonamide.
- Bobylev, V. A.,Petrov, M. L.,Petrov, A. A.
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p. 239 - 245
(2007/10/02)
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- A convenient method for the selective reduction of amides to amines
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A variety of amides have been selectively reduced to the corresponding amines via conversion to their thioamides and treatment with triethyloxonium tetrafluoroborate followed by sodium borohydride. This procedure is compatible with isolated and conjugated double bonds, esters, intro groups, and sulfonamides.
- Raucher, Stanley,Klein, Peter
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p. 4061 - 4064
(2007/10/02)
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