53390-84-4Relevant academic research and scientific papers
Nickel-catalyzed and Li-mediated regiospecific C-H arylation of benzothiophenes
Canivet, Jér?me,Grousset, Léonie,Hisler, Ga?lle,Mohr, Yorck,Quadrelli, Elsje Alessandra,Roux, Yoann,Wisser, Florian M.
, p. 3155 - 3161 (2020/06/19)
A nickel-based catalytic system for the regiospecific C2-H arylation of benzothiophene has been established. NiCl2(bpy) is used as a catalyst in combination with LiHMDS as a base in dioxane. The catalytic system is applicable to a variety of functionalized benzothiophenes, as well as other heteroarenes including thiophene, benzodithiophene, benzofuran and selenophene in combination with iodo aryl electrophiles. The role of LiHMDS as a uniquely potent base and a postulated mechanism are discussed. The applicability of this system is finally demonstrated for the synthesis of an intermediate of an active pharmaceutical ingredient.
Selenophenol quinoline derivative as well as preparation method and application thereof
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Paragraph 0152; 0158-0160, (2020/12/30)
The invention discloses a selenophenol quinoline derivative as well as a preparation method and application thereof. The structure of the selenophenol quinoline derivative is shown as a formula I, a formula II or a formula III, wherein R1 is hydrogen, a C1-6 alkyl group, a C1-6 alkoxy group, a substituted ketone group, a phenyl group, a benzyl group, a substituted phenyl group or a substituted benzyl group; R1 is a monovalent metal cation; R2 is one or more of hydrogen, halogen, a C1-4 alkyl group, a C1-4 alkoxy group or a C1-4 haloalkyl group; R3 is a substituted five-membered heterocyclicring or a substituted six-membered heterocyclic ring; and a heteroatom is one or more of N, O, S or Se. The compound disclosed by the invention is novel in structure, simple in preparation process and relatively good in inhibition effect on various cancer cells, particularly the compounds 34, 44, 45, 98, 104, 115 and 116 have excellent inhibition effects on various cancer cells, the effects of the compounds are equivalent to those of a positive control DDP, and the compounds can be used to prepare anti-cancer drugs to be applied under 5 [mu]M or below, so that the prospect is wide.
Iodine-Catalyzed Synthesis of Chalcogenophenes by the Reaction of 1,3-Dienyl Bromides and Potassium Selenocyanate/Potassium Sulfide (KSeCN/K2S)
Maity, Pintu,Ranu, Brindaban C.
, p. 4369 - 4378 (2017/12/26)
The methods available for the synthesis of chalcogenophenes, in general, are associated with drawbacks of harsh conditions, use of costly metals, broad applicability, tedious purification process and low yield. To avoid these drawbacks a transition metal-free iodine-catalyzed reaction of aryl-susbstituted 1,3-dienyl bromides with potassium selenocyanate/potassium sulfide (KSeCN/K2S) leading to the corresponding selenophenes and thiophenes has been developed. Iodine is relatively benign, less expensive and readily available. Several diversely substituted selenophenes and thiophenes have been obtained by this procedure in high yields. Using this procedure 2-(4-chlorophenyl)thiophene, a key intermediate for the synthesis of a melanin concentrating hormone receptor ligand involved in the treatment of eating disorders, weight gain, obesity, depression and anxiety has been synthesized. Although the reaction is one-pot essentially it proceeds in two steps involving a selenocyanate/thiolate intermediate leading to the selenophene/thiophene. The simple operation, use of inexpensive reagents and a metal-free process make this procedure more attractive for an easy access to substituted selenophenes and thiophenes. (Figure presented.).
Preparation of 1,3-diphenylselenophenotetraazaporphyrinato ruthenium(II) Bis(4-methylpyridine) by the reaction of 3,4-dicyano-2,5-diphenylselenophene and phthalonitrile: Its optical and electrochemical properties
Kimura, Takeshi,Murakami, Naoko
, p. 428 - 433 (2015/04/22)
2,5-Diphenylselenophene (2a) was treated with bromine and then copper(I) cyanide to produce 3,4-dicyano-2,5-diphenylselenophene (4). Compound 4 was mixed with phthalonitrile, and the mixture was reacted with ruthenium(III) trichloride and 4-methylpyridine in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) in refluxed 2-ethoxyethanol to give 1,3-diphenylselenophenotetraazaporphyrinato ruthenium(II) bis(4-methylpyridine) (6). The structure of 6 was determined by 1H NMR and fast atom bombardment mass spectrometry (FABMS). In the 1H NMR spectrum, the signals of 4-methylpyridine coordinating to the central ruthenium atom were observed at a higher magnetic field than those of free 4-methylpyridine itself but at a lower magnetic field than those of phthaocyaninato ruthenium(II) bis(4-methylpyridine) (7). The 77Se NMR spectrum of 6 showed one singlet peak at δ = 759.5 ppm, which is a lower magnetic field than those of 2a and 4. The Q band absorption of 6 (λmax = 660 nm) lies at a longer wavelength than does that of 7. Oxidation and reduction potentials of 6 were measured with cyclic voltammetry using Ag/AgNO3 as a reference electrode.
A direct synthesis of selenophenes by Cu-catalyzed one-pot addition of a selenium moiety to (E,E)-1,3-dienyl bromides and subsequent nucleophilic cyclization
Maity, Pintu,Kundu, Debasish,Roy, Rajdip,Ranu, Brindaban C.
, p. 4122 - 4125 (2014/09/30)
An efficient protocol for the synthesis of selenophenes and selanyl selenophenes has been achieved by a simple one-pot reaction of 1,3-dienyl bromides and 1,3-dienyl-gem-dibromides respectively with KSeCN catalyzed by CuO nanoparticles. Several aryl, alke
Palladium-catalyzed direct arylation of selenophene
Rampon, Daniel S.,Wessjohann, Ludger A.,Schneider, Paulo H.
, p. 5987 - 5992 (2014/07/21)
An efficient and convenient method was developed for the regioselective formation of 2-aryl- or 2,5-diarylselenophenes via a palladium-catalyzed direct arylation. This protocol is suitable for a wide range of aryl halides containing different functional groups. The 2-arylated substrates can undergo an additional regioselective direct arylation event furnishing symmetrical or unsymmetrical 2,5-diaryl selenophenes in good yield. Competition experiments and the role of the acid additive are in agreement with a concerted metalation deprotonation (CMD) pathway.
Cyclization of homopropargyl chalcogenides by copper(II) salts: Selective synthesis of 2,3-dihydroselenophenes, 3-arylselenophenes, and 3-haloselenophenes/thiophenes
Schumacher, Ricardo F.,Rosário, Alisson R.,Leite, Marlon R.,Zeni, Gilson
, p. 13059 - 13064 (2013/10/01)
Copper(II) halide mediated cyclization of homopropargyl chalcogenides gave three types of chalcogenophene derivatives. Selective product formation was achieved by controlling solvent, temperature, and atmosphere. By using CuBr 2 and 1,2-dichlor
Palladium-catalyzed Suzuki cross-coupling of 2-haloselenophenes: Synthesis of 2-arylselenophenes, 2,5-diarylselenophenes, and 2-arylselenophenyl ketones
Prediger, Patricia,Moro, Angelica V.,Nogueira, Cristina W.,Savegnago, Lucielli,Menezes, Paulo Henrique,Rocha, Joao B. T.,Zeni, Gilson
, p. 3786 - 3792 (2007/10/03)
We present herein our results on the Suzuki coupling reaction of 2-haloselenophenes with boronic acids catalyzed by palladium salt and describe a new route established to prepare 2-arylselenophenes and 2,5-diarylselenophenes in good yields. The reaction p
Gas-Phase Reactions of Phenylacetylene with Dialkyl Selenides
Deryagina,Sukhomazova,Levanova,Shilkina
, p. 928 - 935 (2007/10/03)
Gas-phase reactions of phenylacetylene with dialkyl selenides R2Se, where R = Me, Et, Pr, and Bu, were first studied. At 450-570°C, phenylacetylene reacts with dimethyl selenide to give an organoselenium product - 2-phenylselenophene (≤43%), as well as styrene and ethylbenzene. The latter two compounds are the major products of reaction of phenylacetylene with the other dialkyl selenides at 400-600°C. The yield and ethylbenzene:styrene ratio increase with increasing selenide alkyl chain length. With dibutyl selenide, the yield of ethylbenzene is higher than 100%. A comparative study of reactions of phenylacetylene with dialkyl disulfides and with mixtures of dialkyl selenides and dialkyl disulfides was performed. The resulting data were rationalized in terms of phenylacetylene reaction with selenyl and thiyl radicals, generated by pyrolysis of dialkyl chalcogenides. Pyrolysis of individual dialkyl chalcogenides and phenylacetylene was studied.
