22810-28-2Relevant 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
supporting information, p. 75 - 79 (2019/01/04)
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.
Synthesis and reactivity of spiro[1,3,4-thiadiazoline-2,4′- thioflavans] and analogues
Somogyi, Laszlo
experimental part, p. 399 - 409 (2009/09/25)
(Chemical Equation Presented) Racemic thioflavanone (thio)acylhydrazones undergo transformation into racemic 3-acetylspiro[1,3,4-oxa(thia)-diazoline-2, 4′-thioflavans] with trans O(1) or S(1) and Ph(2′eq) under acetylating conditions. Conjugation between the ethylenic bond and sp 2 C(4) in thioflavones encumber both the formation of (thio)acylhydrazones and their subsequent spirocyclization. On the other hand, subsequent dehydrogenation of the thiopyran moiety of spiro compounds results in formation of sp2 C(4) and simultaneous degradation of the spirodiazoline ring.
Chemo- and diastereoselectivity in the dimethyldioxirane oxidation of 2,3-dihydro-4H-1-benzothiopyran-4-ones and 4H-1-benzothiopyran-4-ones. Unusual reactivity of 4H-1-benzothiopyran-4-one 1-oxides1
Patonay,Adam,Levai,Koever,Nemeth,Peters,Peters
, p. 2275 - 2280 (2007/10/03)
The oxidation of the 1-thiochromanones 1-3 by dimethyldioxirane (DMD) produced the corresponding sulfoxides 4-6 or sulfones 7-9; their relative amounts depended on the amount of oxidant used. A low diastereoselectivity was observed in the sulfoxidation of
Transformation of 1-thioflavonoids by oxidation and dehydrogenation
Somogyi
, p. 1857 - 1872 (2007/10/03)
Simple, efficient and selective new one-step transformations with DDQ, IBDA and I2/DMSO are presented for the dehydrogenation of thioflavanone (1α), as well as the oxidized (1c) and halogenated (1d) derivatives. Ring- contraction reactions of the 1-oxide 1b and 1d leading to the formation of the benzothiophen derivatives 3a and 5, respectively, are also described.
Contribution to the Transformations of 1-Thioflavanoids with Hypervalent Oxidants
Somogyi, Laszlo
, p. 959 - 960 (2007/10/02)
Permanganate oxidation transforms 1-thioflavanone (1a) to the corresponding 1,1-dioxide 1c.Periodate oxidation of 1a affords in the cold mainly the corresponding sulfoxide 1b, and that of 1a or 1-thioflavone 1-oxide (2b) provides on heating 1-thioflavone
Chemistry of 1,1-Dioxothiopyrans. 1. Syntheses and Reactions of 2,6-Diphenyl-4H-thiopyran-4-one 1,1-Dioxide and 4H-Thioflaven-4-one, 1,1-Dioxide
Chen, Chin H.,Reynolds, George A.,Luss, H. R.,Perlstein, Jerome H.
, p. 3282 - 3289 (2007/10/02)
Improved syntheses and certain reactions of 2,6-diphenyl-4H-thiopyran-4-one 1,1-dioxide and 4H-thioflaven-4-one 1,1-dioxide are reported.Many of these derivatives, which display reversible, one-electron reduction waves in their cyclic voltammograms betwee
