166045-40-5Relevant academic research and scientific papers
Copper-Catalyzed One-Pot Synthesis of 2-Arylthiochromenones: An in Situ Recycle of Waste Byproduct as Useful Reagent
Sangeetha, Subramani,Sekar, Govindasamy
, p. 75 - 79 (2019)
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.
Synthesis and evaluation of thiochroman-4-one derivatives as potential leishmanicidal agents
Vargas, Esteban,Echeverri, Fernando,Vélez, Iván D.,Robledo, Sara M.,Qui?ones, Wiston
, (2018/01/17)
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.
A rapid entry into thioflavanones via conjugate additions of diarylcuprates to thiochromones
Guo, Fenghai,Jeffries, Malcolm C.,Graves, Briana N.,Graham, Shekinah A.,Pollard, David A.,Pang, Gehao,Chen, Henry Y.
, p. 5745 - 5750 (2017/09/05)
Thiochromone undergo conjugate addition reactions with arylcuprates to afford 2-substituted thioflavanones, providing an efficient synthetic approach to privileged sulfur-containing structural motifs and valuable precursor for many pharmaceuticals. Excellent yields of substituted thioflavanones are achieved with lithium diarylcuprates, lithium arylcyanocuprates and Grignard reagents with copper catalysis. This method provides a rapid entry to a variety of thioflavanones in excellent yields (up to 92%). The use of commercially available or easily prepared organometallic reagents will expedite the synthesis of a large library of thioflavanones for further synthetic applications and biological studies.
Two-Component Assembly of Thiochroman-4-ones and Tetrahydrothiopyran-4-ones Using a Rhodium-Catalyzed Alkyne Hydroacylation/Thio-Conjugate-Addition Sequence
Bouisseau, Ana?s,Glancy, John,Willis, Michael C.
supporting information, p. 5676 - 5679 (2016/11/17)
β′-Thio-substituted-enones, assembled from the combination of β-tert-butylthio-substituted aldehydes and alkynes, using rhodium catalysis, are shown to smoothly undergo in situ intramolecular S-conjugate addition to deliver a range of S-heterocycles in a one-pot process. Aryl, alkenyl, and alkyl aldehydes can all be employed, to provide thiochroman-4-ones, hexahydro-4H-thiochromen-4-ones, and tetrahydrothiopyran-4-ones, respectively. A variety of in situ oxidations are also performed, allowing access to S,S-dioxide derivatives, as well as unsaturated variants.
Copper-Catalyzed Domino Synthesis of 2-Arylthiochromanones through Concomitant C-S Bond Formations Using Xanthate as Sulfur Source
Sangeetha, Subramani,Muthupandi, Pandi,Sekar, Govindasamy
, p. 6006 - 6009 (2016/01/09)
An efficient domino process for the synthesis of thioflavanones has been described using a copper catalyst without addition of any external ligand. A variety of thioflavanones have been synthesized from easily accessible 2′-iodochalcones or 2′-bromochalco
Benzodiazepine analogues. Part 8. Trimethylsilyl azide mediated Schmidt rearrangement of thioflavanone and thiochromanone precursors
Kaye,Mphahlele
, p. 1495 - 1509 (2007/10/02)
The synthesis and Schmidt rearrangement of a series of thioflavanone analogues to benzothiazepinone derivatives is described.
