415680-02-3Relevant articles and documents
Synthesis of Novel Benzothiophene Derivatives via Cyclization Reactions
Algso, M. A. S.,Hama, A. K.,Kavak, E.,Kivrak, A.
, p. 1272 - 1278 (2020)
Abstract: The Sonogashira cross coupling reaction of 2-bromo-5-(4-methoxyphenyl)thiophene and 1-ethynyl-2-(methylsulfanyl)benzene gave 2-(4-methoxyphenyl)-5-{[2-(methylsulfanyl)phenyl]ethynyl}thiophene which was subjected to electrophilic cyclization by t
New strategy for the synthesis of 3-ethynyl-2-(thiophen-2-yl)benzo[b]thiophene derivatives
Algso, Muheb A. S.,Kivrak, Arif
, p. 977 - 985 (2019)
Pd-catalyzed coupling reactions like the Sonogashira coupling reaction are very useful tools for the formation of new carbon–carbon bonds under mild reaction conditions. Coupling reactions are also used for elaboration of organic compounds in drug and material discovery. Terminal alkynes have a very critical role in Sonogashira coupling reaction. Therefore, design and synthesis of new terminal alkynes are very important for the preparation of organic compounds. In the present study, a novel alkyne 3-ethynyl-2-(thiophen-2-yl)benzo[b]thiophene 13 was synthesized, and it was tested for Sonogashira coupling reaction with different iodoaryl compounds. It was investigated whether our terminal alkyne 13 having a special construction might be a useful precursor for the synthesis of potentially active organic molecules.
Nucleophilic C-H Etherification of Heteroarenes Enabled by Base-Catalyzed Halogen Transfer
Bandar, Jeffrey S.,Klaus, Danielle R.,Puleo, Thomas R.
supporting information, p. 12480 - 12486 (2021/08/24)
We report a general protocol for the direct C-H etherification of N-heteroarenes. Potassium tert-butoxide catalyzes halogen transfer from 2-halothiophenes to N-heteroarenes to form N-heteroaryl halide intermediates that undergo tandem base-promoted alcohol substitution. Thus, the simple inclusion of inexpensive 2-halothiophenes enables regioselective oxidative coupling of alcohols with 1,3-azoles, pyridines, diazines, and polyazines under basic reaction conditions.
Iodocyclisation of Electronically Resistant Alkynes: Synthesis of 2-Carboxy (and sulfoxy)-3-iodobenzo[ b ]thiophenes
Chen, Shuqi,Flynn, Bernard L.
, p. 65 - 76 (2020/11/05)
The iodocyclisation of alkynes bearing tethered nucleophiles is a highly effective method for the construction and diversification of heterocycles. A key limitation to this methodology is the 5-endo-dig iodocyclisation of alkynes that have an unfavourable electronic bias for electrophilic cyclisation. These tend to direct electrophilic attack of the iodonium atom to the wrong carbon for cyclisation, thus favouring competing addition reactions. Using our previously determined reaction conditions for the 5-endo-dig iodocyclisations of electronically resistant alkynes, we have achieved efficient synthetic access to 2-carboxy (and sulfoxy)-3-iodobenzo[b]thiophenes. The corresponding benzo[b]furans and indoles were not accessible under these conditions. This difference may arise due to the availability of a radical mechanism in the case of iodobenzo[b]thiophenes. The 2-carboxy functionality of the iodocyclised products can be further employed in iterative alkyne-coupling iodocyclisation reactions, where the carboxy group or an imine (Schiff base) partakes in a second iodocyclisation to generate a lactone or pyridine ring.
B(C6F5)3-Catalyzed cyclization of alkynes: direct synthesis of 3-silyl heterocyclic compounds
Li, Mengxing,Wang, Ting,An, Zhenyu,Yan, Rulong
, p. 11953 - 11956 (2020/10/15)
An efficient one-pot strategy for easy access to 3-silyl heterocyclic compounds was developedviaa B(C6F5)3-catalyzed cycloaddition reaction ofo-(1-alkynyl)(thio)anisoles oro-(1-alkynyl)-N-methylaniline. In this reaction, benzenethiophene, benzofuran or indole skeletons could be constructed by an intermolecular cyclization with diphenylsilane. This protocol elicited moderate-to-good yields with metal-free reaction systems.
Polyynes to Polycycles: Domino Reactions Forming Polyfused Chalcogenophenes
Dillon, Annaliese S.,Flynn, Bernard L.
supporting information, p. 2987 - 2990 (2020/04/09)
Polyfused chalcogenophenes are prepared in one step through polyelectrophilic cyclization of polyynes using the ambiphilic reagent MeACl (A = S, Se, or Te). Up to four new rings have been generated under mild conditions, including thiophenes, selenophenes, and tellurophenes.
Synthesis of [1]Benzothieno[3,2- b][1]benzothiophene Derivatives via Successive Iodocyclization/Photocyclization of Alkynes
Kitamura, Tsugio,Morita, Kazuhiro,Nakamori, Haruka,Oyamada, Juzo
, p. 4191 - 4199 (2019/03/19)
A new synthetic method for [1]benzothieno[3,2-b][1]benzothiophene derivatives (BTBTs) was developed. The present method consists of iodocyclization of 1,2-bis(2-methylthiophenyl)ethynes and photolysis of 3-iodo-(2-methylthiophenyl)benzo[b]thiophenes. With 1,2-bis(2-methylthiophenyl)ethynes treated with I2/PhI(OAc)2 in CH2Cl2 at room temperature, selective cyclization at sulfur took place to give 3-iodo-(2-methylthiophenyl)benzo[b]thiophenes in good yields. Irradiation of the iodinated benzo[b]thiophenes with a high-pressure Hg lamp (>290 nm) provided BTBTs in good yields. Furthermore, the present method was applied to the synthesis of bis[1]benzothieno[2,3-d;2′,3′-d′]benzo[1,2-b;4,5-b′]dithiophene (BBTBDT).
Sodium halides as the source of electrophilic halogens in green synthesis of 3-halo- and 3,n-dihalobenzo[b]thiophenes
Kesharwani, Tanay,Kornman, Cory,Tonnaer, Amanda,Hayes, Amanda,Kim, Seoyoung,Dahal, Nikesh,Romero, Ralf,Royappa, Andrew
, p. 2973 - 2984 (2018/05/23)
A convenient methodology for the synthesis of mono- and di-halogenated benzo[b]thiophenes is described herein, which utilizes copper(II) sulfate pentahydrate and various sodium halides in the presence of substituted 2-alkynylthioanisoles. The proposed met
Synthesis and biological evaluation of novel benzothiophene derivatives
Algso, Muheb A S,Kivrak, Arif,Konus, Metin,Yilmaz, Can,Kurt-Kizildo?an, Aslihan
, (2018/08/17)
Abstract: Benzothiophene derivatives were synthesized regioselectively using coupling reactions and electrophilic cyclization reactions. Antimicrobial properties of isolated compounds were tested against indicator microorganisms such as C. albicans ATCC 10231, B. subtilis ATCC 6633, E. coli ATCC 25922 and S. aureus ATCC 25923. 3-(4-aminobenzoethynyl)-2-(thiophen-2-yl) benzo[b]thiophene (12E), 3-ethynyl-2-(thiophen-2-yl) benzo[b]thiophene (12L) and 3-(2-aminobenzoethynyl)-2-(thiophen-2-yl) benzo[b]thiophene (12J) displayed high antibacterial activity against S. aureus. Further, 3-iodo-2-(thiophen-2-yl) benzo[b]thiophene (10) and 3-(trimethylsilylethynyl)-2-(thiophen-2-yl) benzo[b] thiophene (12K) were found to have potentials to be used as antifungal agents against current fungal diseases. Novel 3-(1H-indole-2-yl)-2-(thiophen-2-yl) benzo[b] thiophene (16) and 3-(4-aminobenzoethynyl)-2-(thiophen-2-yl) benzo[b] thiophene (12E) also showed quite high antioxidant capacities with TEAC values of 2.5 and 1.1, respectively; which surpassed the antioxidant capacity of an universally accepted reference of trolox. Graphical Abstract: Benzothiophene derivatives were synthesized regioselectively using coupling reactions and electrophilic cyclization reactions. Antimicrobial properties of the compounds were tested against four indicator microorganisms, and a few?displayed high antibacterial activity against S. aureus. 3-(1H-indole-2-yl)-2-(thiophen-2-yl)benzo[b]thiophene (16) and 3-(4-aminobenzoethynyl)-2-(thiophen-2-yl)benzo[b]thiophene (12E) showed high antioxidant capacities which are better than the reference of trolox. [Figure not available: see fulltext.].
Enediynes bearing polyfluoroaryl sulfoxide as new antiproliferative agents with dual targeting of microtubules and DNA
Borie, Cyril,Mondal, Shovan,Arif, Tanzeel,Briand, Manon,Lingua, Hugo,Dumur, Frédéric,Gigmes, Didier,Stocker, Pierre,Barbarat, Bernadette,Robert, Viviane,Nicoletti, Cendrine,Olive, Daniel,Maresca, Marc,Nechab, Malek
supporting information, p. 306 - 313 (2018/02/21)
A novel series of enediynes possessing pentafluorophenylsulfoxide have been developed. The innovative compounds possess antiproliferative activity against a broad panel of human cancer cells originating from breast, blood, lung, kidney, colon, prostate, pancreas or skin with IC50 ranging from 0.6 to 3.4 μM. The antiproliferative activity of enediynes in darkness is associated to their ability to compromise microtubule network. In addition, exposure to UV leads to double-stranded DNA cleavage caused by the newly synthesized molecules reducing further their IC50 in nanomolar range against human tumor cells, including chemo-resistant pancreatic cancer cells. Taken together, the examined data demonstrate that enediynes possessing pentafluorosulfoxide are promising molecules in the cancer therapy.
