- Nickel-Catalyzed One-Pot Carbonylative Synthesis of 2-Mono- And 2,3-Disubstituted Thiochromenones from 2-Bromobenzenesulfonyl Chlorides and Alkynes
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A nickel-catalyzed one-pot carbonylation reaction of 2-bromobenzenesulfonyl chlorides with alkynes for the synthesis of thiochromenones has been established. Both terminal and internal alkynes were suitable substrates in this carbonylative transformation, and a broad range of 2-mono- and 2,3-disubstituted thiochromenone products were obtained in moderate to good yields with quite high functional group compatibility. Notably, this procedure presents the first example of nickel-catalyzed carbonylative synthesis of thiochromenones with 2-bromobenzenesulfonyl chlorides as a promising sulfur precursor.
- Wang, Wei,Bao, Zhi-Peng,Qi, Xinxin,Wu, Xiao-Feng
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p. 6589 - 6593
(2021/08/30)
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- Elemental chalcogen (Se, S) in PEG-400 to the synthesis of seleno- And thioflavones from 2-chlorophenyl ethynyl ketone and nucleophilic species of chalcogen
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An alternative green method was developed for the synthesis of thio- and selenoflavones by the ring closure of 2-chlorophenyl ethynyl ketone with NaHY (Y = S, Se). These nucleophilic chalcogen species were generated in situ using NaBH4 to reduc
- Barcellos, Angelita M.,Barcellos, Thiago,Bartz, Ricardo H.,Jacob, Raquel G.,Nobre, Patrick C.,Peglow, Thiago J.,Perin, Gelson,Silva, Márcio S.
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p. 1541 - 1551
(2021/07/06)
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- Competitive cascade cyclization of 2′-tosyloxychalcones: An easy access to thioflavones and thioaurones
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A new and efficient approach for the synthesis of thioflavones and thioaurones by competitive cascade cyclization of 2′-tosyloxychalcones has been developed. 2′-Tosyloxychalcones were smoothly converted into thioflavones and thioaurones by incorporation of sulfur atom using elemental sulfur and triethylamine in DMSO with good yields. The advantages of the methodology are the formation of both thioflavones and thioaurones in a single step. Easily accessible substrates, mild reaction conditions and compatibility with a broad range of functional groups make this protocol clean and inexpensive.
- Venkateswarlu, Somepalli,Murty, Gandrotu Narasimha,Satyanarayana, Meka,Siddaiah, Vidavalur
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supporting information
p. 2347 - 2354
(2020/07/03)
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- Copper-Catalyzed One-Pot Synthesis of 2-Arylthiochromenones: An in Situ Recycle of Waste Byproduct as Useful Reagent
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Copper-catalyzed one-pot synthesis of various 2-arylthiochromenones is developed using xanthate as an odorless sulfur source from easily acquirable 2′-halochalcones. This methodology demonstrates that the cross-coupled product thiochromanone synthesized from 2′-halochalcones (upstream reaction) is oxidized to thiochromenone (downstream reaction) in the same pot using waste byproduct (KI) of the first step as powerful oxidant molecular iodine (I2). This one-pot synthesis has been further extended for the synthesis of 3,3′-methylenebisthioflavone using dimethyl sulfoxide (DMSO) as solvent and methylene source.
- Sangeetha, Subramani,Sekar, Govindasamy
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- Carbonylative Synthesis of Thiochromenones via Palladium-Catalyzed tert -Butyl Isocyanide Insertion
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A flexible and efficient carbonylative synthesis of thiochromenones from the commercially available materials by utilizing tert -butyl isocyanide as carbonyl source has been developed. This methodology efficiently constructs thiochromenones in moderate to excellent yields with the advantages of wide range of substrates and being applicable to library synthesis.
- Zhang, Fang-Ling,Chen, Zhen-Bang,Liu, Kui,Yuan, Qing,Jiang, Qing,Zhu, Yong-Ming
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supporting information
p. 621 - 626
(2018/02/06)
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- Synthesis and evaluation of thiochroman-4-one derivatives as potential leishmanicidal agents
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The S-containing heterocyclic compounds benzothiopyrans or thiochromones stand out as having promising biological activities due to their structural relationship with chromones (benzopyrans), which are widely known as privileged scaffolds in medicinal chemistry. In this work, we report the synthesis of 35 thiochromone derivatives and the in vitro antileishmanial and cytotoxic activities. Compounds were tested against intracellular amastigotes of Leishmania panamensis and cytotoxic activity against human monocytes (U-937 ATCC CRL-1593.2). Compounds bearing a vinyl sulfone moiety, 4h, 4i, 4j, 4k, 4l and 4m, displayed the highest antileishmanial activity, with EC50 values lower than 10 μM and an index of selectivity over 100 for compounds 4j and 4l. When the double bond or the sulfone moiety was removed, the activity decreased. Our results show that thiochromones bearing a vinyl sulfone moiety are endowed with high antileishmanial activity and low cytotoxicity.
- Vargas, Esteban,Echeverri, Fernando,Vélez, Iván D.,Robledo, Sara M.,Qui?ones, Wiston
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- Transition-Metal-Free One-Pot Tandem Synthesis of 4-Quinolone and 4 H -Thiochromen-4-one Derivatives Through Sequential Nucleophilic Addition-Elimination-S N Ar Reaction
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4-Quinolone and 4 H -thiochromen-4-one derivatives are readily synthesized in a tandem one-pot manner in good to excellent yields. Starting from (Z)-β-chlorovinyl ketones, an intermolecular nucleo-philic addition of amines or sodium hydrogen sulfide to (Z
- Wang, Deqiang,Sun, Peng,Jia, Peiyun,Peng, Jinsong,Yue, Yixia,Chen, Chunxia
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p. 4309 - 4320
(2017/09/13)
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- The involvement of the trisulfur radical anion in electron-catalyzed sulfur insertion reactions: Facile synthesis of benzothiazine derivatives under transition metal-free conditions
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An efficient and practical synthesis of benzothiazine by K2S initiated sulfur insertion reaction with enaminones via electron catalysis is developed. This protocol provides a new, environment-friendly and simple strategy to construct benzothiaz
- Gu, Zheng-Yang,Cao, Jia-Jia,Wang, Shun-Yi,Ji, Shun-Jun
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p. 4067 - 4072
(2016/07/06)
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- Transition metal free intramolecular S-arylation: One-pot synthesis of thiochromen-4-ones
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A convenient one-pot method for the synthesis of thiochromen-4-ones by the condensation of 2′-haloacetophenone and dithioesters at room temperature in the presence of NaH in DMF in moderate to good yields has been developed. The method involves unusual intramolecular S-arylation. The reaction is operationally facile, readily scalable and offers rapid entry into substituted chromene-4-ones.
- Jenifer Vijay,Nandeesh, Kebbahalli N.,Raghavendra, Goravanahalli M.,Rangappa, Kanchugarakoppal S.,Mantelingu, Kempegowda
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p. 6533 - 6537
(2013/11/19)
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- Lewis acid-triggered selective zincation of chromones, quinolones, and thiochromones: Application to the preparation of natural flavones and isoflavones
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A Lewis acid-triggered zincation allows the regioselective metalation of various chromones and quinolones. In the absence of MgCl2, a C(3) zincation is observed, whereas in the presence of MgCl2 or a related Lewis acid, C(2) zincation occurs. Applications to a natural flavone, isoflavone, and quinolone are shown.
- Klier, Lydia,Bresser, Tomke,Nigst, Tobias A.,Karaghiosoff, Konstantin,Knochel, Paul
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supporting information; experimental part
p. 13584 - 13587
(2012/10/08)
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- Microwave-assisted three-component coupling-addition-SNAr (CASNAR) sequences to annelated 4H-thiopyran-4-ones
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A whole family of annelated 4H-thiopyran-4-ones as the core structural unit was readily synthesized in good yields by a microwave-assisted coupling-addition-SNAr (CASNAR) sequence starting from readily available (het)aroyl chlorides, alkynes and sodium sulfide nonahydrate in a consecutive one-pot three-component reaction. All representatives display a pronounced halochromicity of the absorption bands upon protonation. According to DFT calculations, the electronic ground state of the annelated 4H-thiopyran-4-ones possess a considerable zwitterionic character. The Royal Society of Chemistry 2010.
- Willy, Benjamin,Frank, Walter,Mueller, Thomas J. J.
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supporting information; experimental part
p. 90 - 95
(2010/04/26)
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- A novel consecutive three-component coupling-addition-SNAr (CASNAR) synthesis of 4H-thiochromen-4-ones
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4H-Thiochromen-4-ones and 4H-thiopyrano[2,3-b]pyridin-4-ones are readily synthesized in good yields by a consecutive one-pot, three-component coupling-addition-SNAr (CASNAR) sequence starting from aroyl chlorides, alkynes, and sodium sulfide no
- Willy, Benjamin,Müller, Thomas J. J.
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experimental part
p. 1255 - 1260
(2009/08/14)
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- A new synthesis of 4H-1-benzothiopyran-4-ones using (trimethylsilyl)methylenetriphenylphosphorane
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The reaction of silyl ester of S-acyl(aroyl) thiosalicylic acids 3 with (trimethylsilyl)methylenetriphenylphosphorane 4 in step wise fashion leads to the acylphosphoranes 7, which subsequently undergo intramolecular Wittig cyclization on the thiolester carbonyl to afford the 4H-1-benzothiopyran-4-ones 8 in good to excellent yields.
- Kumar, Pradeep,Bodas, Mandar S
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p. 9755 - 9758
(2007/10/03)
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- A New Preparation of Substituted 4H-1-Benzothiopyran-4-ones from C(α),N-Benzoylhydrazones or C(α),N-Carboalkoxyhydrazones and Methyl Thiosalicylate
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C(α),N-Benzoylhydrazones or C(α),N-carboalkoxyhydrazones were dilithiated with excess lithium diisopropylamide, and the dianion-type intermediates were condensed with lithiated methyl thiosalicylate, followed by cyclization/hydrolysis to substituted 4H-1-benzothiopyran-4-ones (thioflavones/thiochromones).
- French, Kristen L.,Angel, April J.,Williams, Angela R.,Hurst, Douglas R.,Beam, Charles F.
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- An Efficient Approach to the Synthesis of 4H-1-Benzothiopyran-4-ones via Intramolecular Wittig Reaction
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The reaction of S-acyl(aroyl)thiosalicylic acids 2 with N-phenyl(triphenylphosphoranylidene)ethenimine 3 in stepwise fashion leads to the acylphosphoranes 5 which subsequently undergo intramolecular Wittig cyclization on the thiolester carbonyl to afford
- Kumar, Pradeep,Rao, Ashok T.,Pandey, Bipin
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p. 1580 - 1581
(2007/10/02)
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