- Palladium-Catalyzed Domino Cyclization/Phosphorylation of gem-Dibromoolefins with P(O)H Compounds: Synthesis of Phosphorylated Heteroaromatics
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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
- Chen, Chen,Ding, Jie,Liu, Liying,Huang, Yujie,Zhu, Bolin
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supporting information
p. 200 - 205
(2021/10/29)
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- Synthesis and evaluation of antileishmanial and cytotoxic activity of benzothiopyrane derivatives
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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.
- Ortiz, Cristian,Echeverri, Fernando,Robledo, Sara,Lanari, Daniela,Curini, Massimo,Qui?ones, Wiston,Vargas, Esteban
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- Fabrication of egg shell-like nanovesicles from a thiocoumarin-based ?-amino ester: A potential carrier
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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 ?
- Debnath, Mintu,Sasmal, Supriya,Haldar, Debasish
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p. 5450 - 5457
(2017/07/22)
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- SULFUR CHELATED RUTHENIUM COMPOUNDS USEFUL AS OLEFIN METATHESIS CATALYSTS
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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.
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Paragraph 0066
(2014/06/23)
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- Preparation of 4,7-dibromobenzo[b]thiophene as a versatile building block and synthetic application to a bis(ethynylthienyl)oligoarene system
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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.
- Yamamoto, Takuya,Katsuta, Hiroshi,Toyota, Kozo,Iwamoto, Takeaki,Morita, Noboru
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scheme or table
p. 613 - 623
(2012/06/29)
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- Copper-free sonogashira coupling reaction using a trans-spanning 1,2-Bis(2-thienylethynyl)benzene ligand
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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.
- Atobe, Shingo,Sonoda, Motohiro,Suzuki, Yuki,Shinohara, Hiroyuki,Yamamoto, Takuya,Ogawa, Akiya
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supporting information; experimental part
p. 980 - 982
(2012/02/01)
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- An investigation of Cu(II) and Ni(II)-catalysed hydrolysis of (di)imines
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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.
- Czaun, Miklós,Nelana, Simphiwe M.,Guzei, Ilia A.,Hasselgren, Catrin,Hkansson, Mikael,Jagner, Susan,Lisensky, George,Darkwa, James,Nordlander, Ebbe
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scheme or table
p. 3102 - 3112
(2011/03/17)
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- Efficient method for synthesis of 2-acetylbenzo(b)thiophene and its derivatives, the key synthons for 5-lipoxygenase inhibitors
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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
- Chemburkar, Sanjay R.,Anderson, David G.,Reddy, Rajarathnam E.
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experimental part
p. 1887 - 1894
(2010/09/07)
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- Ascorbate mediated copper catalyzed reductive cross-coupling of disulfides with aryl iodides
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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.
- Martinek, Marek,Korf, Michal,Srogl, Jiri
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supporting information; experimental part
p. 4387 - 4389
(2010/08/06)
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- One-pot synthesis of 2H-thiochromenes via TiCl4-promoted reaction of 2-tert-butylthiobenzaldehydes with activated alkenes
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(Chemical Equation Presented) A facile synthesis of 2H-thiochromenes through TiCl4-promoted reaction of 2-tert-butylthiobenzaldehydes with activated alkenes is described.
- Chang, Hoon Lee,Lee, Kee-Jung
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experimental part
p. 1023 - 1027
(2009/12/06)
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- Sulfur chelated ruthenium compounds useful as olefin metathesis catalysts
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Sulfur chelated ruthenium compounds and methods and compositions involving the same. A method may relate to subjecting an olefin to a metathesis reaction in the presence of a sulfur chelated ruthenium compound. A composition may relate to an olefin starting material dissolved in an organic solvent together with a sulfur chelated ruthenium compound.
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- Intramolecular cross-coupling of gem-dibromoolefins: A mild approach to 2-bromo benzofused heterocycles
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Highly useful halogenated benzofurans and benzothiophenes are prepared from readily available gem-dibromoolefins using a mild, ligand-free copper catalyzed cross-coupling procedure.
- Newman, Stephen G.,Aureggi, Valentina,Bryan, Christopher S.,Lautens, Mark
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supporting information; experimental part
p. 5236 - 5238
(2010/01/31)
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- Latent sulfur chelated ruthenium catalysts: Steric acceleration effects on olefin metathesis
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A series of sulfur chelated dormant ruthenium olefin metathesis catalysts is presented. The catalysts prepared were shown to possess the uncommon cis-dichloro arrangement and were mostly inactive at room temperature. By systematically modifying the size of the substituent groups at the chelating sulfur atom, catalyst activity at different temperatures was significantly affected; more bulky substituents fomented activity at lower temperatures. The catalysts were also shown to be stable in solution and retained their catalytic activity even after being exposed to air for two weeks.
- Kost, Tamar,Sigalov, Mark,Goldberg, Israel,Ben-Asuly, Amos,Lemcoff, N. Gabriel
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p. 2200 - 2203
(2008/09/21)
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- Titanium reagents for the synthesis of 2-substituted benzo[b]thiophenes on the solid phase
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Titanium(IV) benzylidenes (Schrock carbenes) bearing a masked sulfur nucleophile in the ortho position were generated from thioacetals with use of low-valent titanocene complex Cp2Ti[P(OEt)3]2 and alkylidenated Merrifield resin-bound esters to give enol ethers. Treatment of the resin-bound enol ethers with a 5:5:90 mixture of TFA, TFAA, and dichloromethane led to cleavage from resin, removal of the tert- butyldimethylsilyl (TBDMS) protecting group, and concomitant cyclization to complete the traceless solid-phase synthesis (SPS) of benzothiophenes. Switching the nature of the linker from acid-stable to acid-sensitive ensured good purity.
- Roberts, Christine F.,Hartley, Richard C.
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p. 6145 - 6148
(2007/10/03)
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- Method for producing 1,2-benzisothiazol-3-ones
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A method for producing a 1,2-benzisothiazol-3-one, having the steps of carrying out a reaction of a 2-(alkylthio)benzaldehyde with a hydroxylamine to give a 2-(alkylthio)benzaldehyde oxime and carrying out a reaction of the 2-(alkylthio)benzaldehyde oxime with a halogenating agent; and a method for producing a 1,2-benzisothiazol-3-one, having the steps of carrying out a reaction of a 2-halobenzonitrile with an alkanethiol in a heterogeneous solvent system in the presence of a base to give a 2-(alkylthio)benzonitrile and carrying out a reaction of the 2-(alkylthio)benzonitrile with an halogenating agent in the presence of water.
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- Process for the production of 2-acetylbenzo [β]thiophenes
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A process for the production in high yield of 2-acetylbenzo[β]thiophene and its alkyl and alkoxy substituted derivatives by converting a 2-halobenzaldehyde to a 2,2'-dithiobis(benzaldehyde) intermediate and reacting that intermediate successively with 2,4-pentanedione and chloroacetone in the presence of base.
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- α',α'-DISILYLATED TERTIARY BENZAMIDES AS DUAL ORTHO- AND α'-CARBANION SYNTHONS. AMIDE PETERSON OLEFINATION ROUTES TO N-BENZOYL ENAMINES, ISOQUINOLINES, AND DIBENZAZOCINES
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α',α'-Disilylated benzamides 2, prepared by LiTMP/TMSCl in situ trap procedure, constitute ortho- and α'-carbanion synthons which provide N-benzoyl enamines (5), isoquinolines (6), dibenzoazocines (9) by Peterson olefination, and pyrroles (11) by cycloaddition.The conversion of 2 into other useful functionality is described.
- Cuevas, J.-C.,Patil, P.,Snieckus, V.
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p. 5841 - 5844
(2007/10/02)
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- Sur le mecanisme de la Reaction de Meth-Cohn-Tarnowski de preparation des thiocoumarines
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Reaction of 2-t-butylthiobenzaldehyde with N-(2-dialkylaminoethyl)-cyanacetamides followed by heating of the resulting 3-(2-t-butylthiophenyl)-2-cyanoacrylamides in polyphosphoric acid leads to the formation of 3-carboxamido-2-imino-2H-benzothiopyrane intermediates which afford thiocoumarins on hydrolysis.The authors postulate the intermediate formation of a thiophenate ion by an electronic mechanism involving six centers.
- El-Ahmad, Youssef,Reynaud, Pierre
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p. 711 - 714
(2007/10/02)
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