65924-65-4Relevant academic research and scientific papers
Palladium-Catalyzed Domino Cyclization/Phosphorylation of gem-Dibromoolefins with P(O)H Compounds: Synthesis of Phosphorylated Heteroaromatics
Chen, Chen,Ding, Jie,Liu, Liying,Huang, Yujie,Zhu, Bolin
supporting information, p. 200 - 205 (2021/10/29)
We presented a palladium-catalyzed domino cyclization/phosphorylation of gem-dibromoolefins, which utilize H-phosphinates and secondary phosphine oxides as the phosphine sources, respectively. A variety of phosphorylated heteroaromatics were obtained in m
Synthesis and evaluation of antileishmanial and cytotoxic activity of benzothiopyrane derivatives
Ortiz, Cristian,Echeverri, Fernando,Robledo, Sara,Lanari, Daniela,Curini, Massimo,Qui?ones, Wiston,Vargas, Esteban
, (2020/02/25)
In continuation of our efforts to identify promising antileishmanial agents based on the chroman scaffold, we synthesized several substituted 2H-thiochroman derivatives, including thiochromenes, thichromanones and hydrazones substituted in C-2 or C-3 with carbonyl or carboxyl groups. Thirty-two compounds were thus obtained, characterized, and evaluated against intracellular amastigotes of Leishmania (V) panamensis. Twelve compounds were active, with EC50 values lower than 40 μM, but only four compounds displayed the highest antileishmanial activity, with EC50 values below 10 μM; these all compounds possess a good Selectivity Index > 2.6. Although two active compounds were thiochromenes, a clear structure-activity relationship was not detected since each active compound has a different substitution pattern.
Fabrication of egg shell-like nanovesicles from a thiocoumarin-based ?-amino ester: A potential carrier
Debnath, Mintu,Sasmal, Supriya,Haldar, Debasish
, p. 5450 - 5457 (2017/07/22)
Nanoscale egg shell-like drug delivery systems from methyl 6-amino-2-oxo-2H-thiochromene-3-carboxylate, a thiocoumarin-based ?-amino ester, have been investigated as potential candidates for drug delivery vehicles. X-ray crystallography reveals that the ?
SULFUR CHELATED RUTHENIUM COMPOUNDS USEFUL AS OLEFIN METATHESIS CATALYSTS
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Paragraph 0066, (2014/06/23)
Sulfur chelated ruthenium compounds represented by the following formula: wherein M indicates the ruthenium metal bound to a benzylidene carbon; R represents C1-C7 alkyl group or optionally substituted aryl; X1 and X2 each independently represent halogen; Y1 and Y2 each independently denote unsubstituted or alkyl-substituted phenyl; and Z independently represents hydrogen, electron withdrawing or electron donating substituent, with m being an integer from 1 to 4, and processes and compositions related thereto.
Preparation of 4,7-dibromobenzo[b]thiophene as a versatile building block and synthetic application to a bis(ethynylthienyl)oligoarene system
Yamamoto, Takuya,Katsuta, Hiroshi,Toyota, Kozo,Iwamoto, Takeaki,Morita, Noboru
scheme or table, p. 613 - 623 (2012/06/29)
Benzo[b]thiophene, 4,7-dibromobenzo[b]thiophene, thieno[3,2-b]thiophene, and 3-bromothieno[3,2-b]thiophene were prepared by AuCl-catalyzed cyclization of (t-butylsulfanyl)(ethynyl)benzenes or (t-butylsulfanyl)(ethynyl)thiophenes. Several reactions of 4,7-dibromobenzo[b]thiophene were investigated, including metallation and cross coupling reactions.
Copper-free sonogashira coupling reaction using a trans-spanning 1,2-Bis(2-thienylethynyl)benzene ligand
Atobe, Shingo,Sonoda, Motohiro,Suzuki, Yuki,Shinohara, Hiroyuki,Yamamoto, Takuya,Ogawa, Akiya
supporting information; experimental part, p. 980 - 982 (2012/02/01)
Novel copper-free Sonogashira coupling reaction of aryl halides with terminal acetylenes proceeded in the presence of 1,2-bis(2-thienylethynyl) benzene (1) as a trans-bidentatable ligand.
An investigation of Cu(II) and Ni(II)-catalysed hydrolysis of (di)imines
Czaun, Miklós,Nelana, Simphiwe M.,Guzei, Ilia A.,Hasselgren, Catrin,Hkansson, Mikael,Jagner, Susan,Lisensky, George,Darkwa, James,Nordlander, Ebbe
scheme or table, p. 3102 - 3112 (2011/03/17)
The reactions of six diimine ligands with Cu(II) and Ni(II) halide salts have been investigated. The diimine ligands were Ph2CN(CH 2)nNCPh2 (n = 2 (Bz2en, 1a), 3 (Bz2pn, 1b), 4 (Bz2bn, 1c)), N,N′-bis-(2-tert- butylthio-1-ylmethylenebenzene)-2,2′diamino-biphenyl (2), N,N′-bis-(2-chloro-1-ylmethylenebenzene)-1,3-diaminobenzene (3) and N,N′-bis-(2-chloro-1-ylmethylenebenzene)-1,2-ethanediamine (4). Reactions of 1a-c, 2-4 with CuCl2·2H2O in dry ethanol at ambient temperature led to complete or partial hydrolysis of the diimine ligands to ultimately form copper diamine complexes. The non-hydrolyzed complexes of 1b and 1c, [Cu(L)Cl2] (L = 1b, 1c), could be isolated when the reactions were carried out at low temperatures, and the half-hydrolyzed complex [Cu(Bzpn)Cl2] could also be identified via X-ray crystallography. Similarly, reactions of 1a or 1b with NiCl2·6H2O or [NiBr2(dme)] led to rapid hydrolysis of the imines and Ni complexes containing half-hydrolyzed 1a (Bzen; [trans-[Ni(Bzen)2Br 2]) and 1b (Bzpn; [Ni(Bzpn)Br2] could be isolated and identified via single crystal X-ray analysis. Kinetic studies were made of the hydrolyses of 1a, 1b in THF and 2 in acetone, in the presence of Cu(II), and of 1a in acetonitrile, in the presence of Ni(II). Activation parameters were determined for the latter reaction and for the copper-catalyzed hydrolysis of 2; the relatively large negative activation entropies clearly indicate rate-determining steps of an associative nature.
Efficient method for synthesis of 2-acetylbenzo(b)thiophene and its derivatives, the key synthons for 5-lipoxygenase inhibitors
Chemburkar, Sanjay R.,Anderson, David G.,Reddy, Rajarathnam E.
experimental part, p. 1887 - 1894 (2010/09/07)
An efficient method was developed for synthesis of 2-acetylbenzo(b) thiophene (2a), the key intermediate for zileuton (1). Synthesis involves treatment of 2-chlorobenzaldehyde (5a) with tert-butylmercaptan (6) to form 2-(tert-butylthio)benzaldehyde (7a), which upon treatment with HBr in water gave the disulfide derivative 2,2'-disulfanediyldibenzaldehyde (8a) in 97% yield. Finally, the reaction of 8a with acetylacetone (9) and 1-chloroacetone (10) gave 2-acetylbenzo(b)thiophene (2a) in 94% yield. The methodology is general and suitable for the preparation of its derivatives, 2b-d. Copyright
Ascorbate mediated copper catalyzed reductive cross-coupling of disulfides with aryl iodides
Martinek, Marek,Korf, Michal,Srogl, Jiri
supporting information; experimental part, p. 4387 - 4389 (2010/08/06)
The concept of using ascorbic acid as a mediator/ reducing agent in a Cu(i) catalyzed process is introduced and further demonstrated on a cross-coupling reaction of aryl iodides with disulfides.
One-pot synthesis of 2H-thiochromenes via TiCl4-promoted reaction of 2-tert-butylthiobenzaldehydes with activated alkenes
Chang, Hoon Lee,Lee, Kee-Jung
experimental part, p. 1023 - 1027 (2009/12/06)
(Chemical Equation Presented) A facile synthesis of 2H-thiochromenes through TiCl4-promoted reaction of 2-tert-butylthiobenzaldehydes with activated alkenes is described.
