- A New Simple Synthesis of Variously Substituted Furans and Butenolides
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The reaction of 1,2-disubstituted 3,3-bis(methylthio)prop-2-en-1-ones with dimethylsulfonium methylide gave 2,2-bis(methylthio)-2,5-dihydrofurans, useful synthons for a variety of furans and butenolides.
- Okazaki, Renji,Negishi, Yoshio,Inamoto, Naoki
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- Palladium nanoparticles embedded on thiourea-modified chitosan: A green and sustainable heterogeneous catalyst for the Suzuki reaction in water
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Palladium nanoparticles (PdNPs) embedded on thiourea modified chitosan (TMC) are prepared in spherical and cubical shapes by intercalating palladium(ii) acetate in TMC, a natural bio-polymer, and a subsequent reduction using ellagic acid (EA) as a natural and green reducing source in water. The formation of palladium nanoparticles in water is monitored by UV-Vis, spectroscopy and the PdNPs/TMC solid matrix are characterized by FT-IR, powder XRD and HR-TEM. The amount of palladium entrapped on TMC is measured by ICP-OES analysis, and it is found to be 0.00103 mol%. The synthesised PdNPs/TMC reported for the first time, were employed as heterogeneous catalysts for Suzuki cross-coupling reactions of aryl iodide/bromide with various substituted aryl boronic acids in water and showed high catalytic activity under mild reaction conditions. Easy separation, the absence of an inert atmosphere and good to excellent yields are the other significant outcomes of this protocol. In addition, the reactions also work well with various heterocyclic boronic acids. Also the catalyst can be easily recovered and reused for at least five runs without loss in its activity.
- Affrose, Abdullah,Suresh, Palaniswamy,Azath, Ismail Abulkalam,Pitchumani, Kasi
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- Highly active NHC-Pd(ii) complexes for cross coupling of aryl chlorides and arylboronic acids: An investigation of the effect of remote bulky groups
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A series of palladium(ii) complexes bearing remote bulky ligands were synthesized and characterized. Their catalytic activity for Suzuki-Miyaura cross-coupling reactions and the effect of remote bulky groups were investigated. These new palladium complexes are highly efficient for the Suzuki-Miyaura cross-coupling reactions of aryl chlorides and arylboronic acids with low catalyst loadings (0.05 mol%) at room temperature in air.
- Han, Fangwai,Xu, Ying,Zhu, Rongjiao,Liu, Guiyan,Chen, Chen,Wang, Jianhui
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- Highly active palladium catalysts containing a 1,10-phenanthroline analogue N-heterocyclic carbene for room temperature Suzuki-Miyaura coupling reactions of aryl chlorides with arylboronic acids in aqueous media
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Two new palladium (II) complexes containing a 1,10-phenanthroline analogue N-heterocyclic carbene (NHC) have been synthesized. The complexes were characterized by 1H and 13C NMR spectroscopy and elemental analysis and their structures were determined by single-crystal X-ray diffraction. The NHC-palladium complexes were employed as catalysts for Suzuki-Miyaura coupling reactions of aryl chlorides with arylboronic acids in aqueous media at room temperature. The cross-coupling reactions were highly efficient with low catalysts loadings.
- Liu, Guiyan,Liu, Chengxin,Han, Fangwai,Wang, Zhongliang,Wang, Jianhui
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- A SIMPLE, EFFICIENT SYNTHESIS OF 3-SUBSTITUTED FURANS
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3-Substituted furan can be readily prepared in a single step via a tandem Diels-Alder/retro Diels-Alder reaction between 4-phenyloxazole and simple alkylacetylenes.
- Liotta, Dennis,Saindane, Manohar,Ott, Walter
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- Synthesis of 3-substituted furans by hydroformylation
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A simple and novel method for the synthesis of 3-substituted furans by the hydroformylation of substituted propargylic alcohols is described using rhodium acetate and triphenylphosphine in dichloromethane. The hydroformylation reaction proceeds in a regio
- Nanayakkara, Peru,Alper, Howard
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- An improved synthesis of 3-substituted furans from substituted butene- 1,4-diols
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A two-phase mixture of water and hexanes improves the yields of furans produced by the oxidation of butene-1,4-diols.
- Kraus, George A.,Wang, Xuemei
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- The Synthesis and Catalytic Activity of New Mixed NHC-Phosphite Nickel(0) Complexes
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Herein we describe the synthesis and isolation of the first low-valent NHC-phosphite nickel complexes of general formula Ni(NHC)[P(OAr)3]2. These three-coordinate Ni(0) compounds were fully characterized, including by X-ray crystallography that highlighted their trigonal planar geometry. The representative complex Ni(IMes)[P(OPh)3]2 was used to show that a phosphite ligand is readily substituted in the presence of an aldehyde or nitrile. These stoichiometric studies then led to an investigation of their catalytic properties in the Suzuki-Miyaura cross-coupling reactions between aryl tosylates and aryl boronic acids, a first for such a NHC-Ni catalyst. Finally, mechanistic investigations led to the isolation of a well-defined oxidative addition product.
- Dorta, Reto,Duczynski, Jeremy,Moggach, Stephen A.,Sobolev, Alexandre N.,Stewart, Scott G.
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supporting information
(2020/01/21)
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- A Bipyridine-Palladium Derivative as General Pre-Catalyst for Cross-Coupling Reactions in Deep Eutectic Solvents
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A versatile and DES-compatible bipyridine palladium complex has been developed as a general pre-catalyst for different cross-coupling reactions (Hiyama, Suzuki-Miyaura, Heck-Mizoroki and Sonogashira) in deep eutectic solvents. Hydrogen bond capacity of the ligand allows to keep the excellent level of results previously obtained in classical organic solvents. Palladium pre-catalyst showed a high catalytic activity for many cross-coupling reactions, demonstrating a great versatility and applicability. Also, this methodology employs sustainable solvents as a reaction medium and highlights the potential of DES as alternative solvents in organometallic catalysis. The catalyst and DES were easily and successfully recycled. The formation of PdNPs in DES has been confirmed by TEM and XPS analysis and their role as catalyst by mercury test. The dynamic coordination of bipyridine-type ligand in the palladium complex formation has been studied via UV/Vis. (Figure presented.).
- Saavedra, Beatriz,González-Gallardo, Nerea,Meli, Alessandro,Ramón, Diego J.
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supporting information
p. 3868 - 3879
(2019/07/12)
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- Denitrogenative Pd/Cu-catalyzed Suzuki-type Cross-coupling of Aryltrifluoroborates with Arylhydrazine Hydrochlorides in Water under Room Temperature
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A water-soluble palladium-catalyzed Suzuki-type cross-coupling of aryltrifluoroborates with arylhydrazide hydrochlorides was efficiently developed under mild and environmentally benign conditions, in water without any ligand. The newly developed Pd/Cu co-catalyzed denitrogenative reaction gave a range of structurally diverse substituted biaryls with good to excellent yields, in which the byproduct was nitrogen.
- Wang, Guofang,Meng, Mengting,Deng, Liping,Cheng, Kai,Qi, Chenze
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- Nickel-Catalyzed Deamidative Step-Down Reduction of Amides to Aromatic Hydrocarbons
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To date, cleavage of the C-N bond in aromatic amides has been achieved in molecules with a distorted constitutional framework around the nitrogen atom. In this report, a nickel-catalyzed reduction of planar amides to the corresponding lower hydrocarbon homologue has been reported. This involves a one-pot reductive cleavage of the C-N bond followed by a tandem C-CO bond break in the presence of a hydride source. Substrate scope circumscribes deamidation examples which proceed via oxidative addition of nickel in the amide bonds of nontwisted amides. Mechanistic studies involving isolation and characterization of involved intermediates via different spectroscopic techniques reveal a deeper introspection into the plausible catalytic cycle for the methodology.
- Dey, Aniruddha,Sasmal, Sheuli,Seth, Kapileswar,Lahiri, Goutam Kumar,Maiti, Debabrata
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p. 433 - 437
(2017/06/05)
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- Oxygen Activated, Palladium Nanoparticle Catalyzed, Ultrafast Cross-Coupling of Organolithium Reagents
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The discovery of an ultrafast cross-coupling of alkyl- and aryllithium reagents with a range of aryl bromides is presented. The essential role of molecular oxygen to form the active palladium catalyst was established; palladium nanoparticles that are highly active in cross-coupling reactions with reaction times ranging from 5 s to 5 min are thus generated in situ. High selectivities were observed for a range of heterocycles and functional groups as well as for an expanded scope of organolithium reagents. The applicability of this method was showcased by the synthesis of the [11C]-labeled PET tracer celecoxib.
- Heijnen, Dorus,Tosi, Filippo,Vila, Carlos,Stuart, Marc C. A.,Elsinga, Philip H.,Szymanski, Wiktor,Feringa, Ben L.
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supporting information
p. 3354 - 3359
(2017/03/17)
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- Ligand-free Suzuki-Miyaura coupling using ruthenium(0) nanoparticles and a continuously irradiating microwave system
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We developed a conceptually and methodologically novel ruthenium(0) nanoparticle catalyst, sulfur-modified Au-supported ruthenium nanoparticles (SARu). SARu is easily prepared through a three-step procedure involving simultaneous in situ metal nanoparticle and nanospace organization. This unique method does not require any conventional preformed template to immobilize and stabilize metal nanoparticles. SARu is an ideal ruthenium catalyst for liquid-phase combinatorial synthesis because it repeatedly catalyzes ligand-free Suzuki-Miyaura coupling of aryl halides, including aryl chlorides, with arylboronic acids with low Ru leaching. Physical analysis of SARu showed that the active species in these reactions were ruthenium (0) nanoparticles with a size of 1-3 nm. Also, we developed a continuously irradiating microwave methodology, which can first time discriminate the heating effect and the microwave effect in microwave experiments.
- Akiyama, Toshiki,Taniguchi, Takahisa,Saito, Nozomi,Doi, Ryohei,Honma, Tetsuo,Tamenori, Yusuke,Ohki, Yuuta,Takahashi, Naoyuki,Fujioka, Hiromichi,Sato, Yoshihiro,Arisawa, Mitsuhiro
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p. 3357 - 3369
(2017/07/28)
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- Sodium Chloride Catalyzed Regioselective Trifluoromethylthiolation of Furans
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Here, we report the catalytic trifluoromethylthiolation of furans employing sodium chloride as an inexpensive, abundant and ecologically friendly catalyst. The developed method exhibits perfect regioselectivity and a high functional group tolerance. Furth
- Ernst, Johannes B.,Rakers, Lena,Glorius, Frank
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supporting information
p. 260 - 268
(2016/12/24)
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- Visible-light-induced regioselective synthesis of polyheteroaromatic compounds
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A method for visible-light-induced synthesis of polyheteroaromatics from 2-heteroaryl-substituted anilines and heteroarylalkynes was developed. The process, which uses fac-Ir(ppy)3 as the photocatalyst and tBuONO as the diazotization reagent, is highly regioselective.
- Chatterjee, Tanmay,Choi, Myung Gil,Kim, Jun,Chang, Suk-Kyu,Cho, Eun Jin
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p. 4203 - 4206
(2016/03/19)
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- Iodine-Promoted Metal-Free Aromatization: Synthesis of Biaryls, Oligo p-Phenylenes and A-Ring Modified Steroids
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We describe efficient procedures based on the use of iodine for the synthesis of biaryls from arylcyclohexenols or arylcyclohexanols using sub-stoichiometric/catalytic iodine and dimethyl sulfoxide (DMSO) as oxidant. Heteroarylcyclohexanols also produced the corresponding biaryl products. It was proven that biphenyl can also be efficiently obtained when the quantity of iodine was reduced to 0.05 equiv. The method is compatible with different functional groups in the aromatic ring (either electron-donating or electron-withdrawing groups). For substrate scope, apart from cyclohexanone and cyclohexenone, some substituted cyclohexanones were also used to synthesize the starting arylcyclohexanols. The process was applied to the synthesis of oligo p-phenylenes and A-ring aromatized steroids, where the combined use of I2/DMSO not only provoked the necessary migration of the methyl group at C-10, but also further extended the conjugation.
- Domingo, Victoriano,Prieto, Consuelo,Castillo, Alexis,Silva, Lucia,Quílez Del Moral, José F.,Barrero, Alejandro F.
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supporting information
p. 3359 - 3364
(2015/11/03)
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- N,N,N′,N′-tetra(diphenylphosphinomethyl)pyridine-2,6-diamine/palladium catalyzed Suzuki-Miyaura coupling of aryl and heteroaryl halides
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An easily synthesized tetraphosphine N,N,N′,N′-tetra(diphenylphosphinomethyl)-pyridine-2,6-diamine (TPPDA) in combination with PdCl2 was proved to be a highly efficient catalyst for Suzuki-Miyaura cross-coupling. This system could catalyze a variety of aryl halide substrates with a wide range of functional groups as well as heteroaryl halides. A high turnover number (TON) up to 3,350,000 was reached for 3-bromochlorobenzene.
- Guo, Fei-Chen,Zhou, Rong,Jiang, Zhi-Jie,Wang, Wei,Fu, Hai-Yan,Zheng, Xue-Li,Chen, Hua,Li, Rui-Xiang
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- Asymmetric hydrogenation of furans and benzofurans with iridium-pyridine-phosphinite catalysts
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Enantioselective hydrogenation of furans and benzofurans remains a challenging task. We report the hydrogenation of 2- and 3-substituted furans by using iridium catalysts that bear bicyclic pyridine-phosphinite ligands. Excellent enantioselectivities and high conversions were obtained for monosubstituted furans with a 3-alkyl or 3-aryl group. Furans substituted at the 2-position and 2,4-disubstituted furans proved to be more difficult substrates. The best results (80-97% conversion, 65-82% enantiomeric excess) were obtained with monosubstituted 2-alkylfurans and 2-[4-(trifluoromethyl)phenyl]furan. Benzofurans with an alkyl substituent at the 2- or 3-position also gave high conversions and enantioselectivity, whereas 2-aryl derivatives showed essentially no reactivity. The asymmetric hydrogenation of a 3-methylbenzofuran derivative was used as a key step in the formal total synthesis of the cytotoxic naphthoquinone natural product (-)-thespesone.
- Pauli, Larissa,Tannert, Re,Scheil, Robin,Pfaltz, Andreas
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supporting information
p. 1482 - 1487
(2015/01/30)
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- General suzuki coupling of heteroaryl bromides by using tri-tert-butylphosphine as a supporting ligand
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A general procedure for the fast Suzuki coupling of major families of heteroaryl bromides was realized by using Pd(OAc)2/PtBu3 as the catalyst. Many couplings were finished within minutes at room temperature in n-butanol. Different from previous studies, three typical heteroaryl bromides were systematically examined in couplings of various heteroaryl and aryl boronic acids. A fast, general coupling of heteroaryl bromides is realized by using a single palladium catalyst supported by tri-tert-butylphosphine.
- Zou, Yinjun,Yue, Guizhou,Xu, Jianwei,Zhou, Jianrong
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supporting information
p. 5901 - 5905
(2015/03/30)
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- Poly(ethylene glycol) as a reaction matrix in platinum- or gold-catalyzed cycloisomerization: A mechanistic investigation
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Design for diversity: A new catalytic system based on PEG-3400 and a metal salt (Pt or Au) was designed to efficiently perform a cycloisomerization reaction under microwave irradiation, which gave diverse heterocycles in good to excellent yields, after a
- Spina, Rosella,Colacino, Evelina,Martinez, Jean,Lamaty, Frédéric
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p. 3817 - 3821
(2013/04/24)
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- Cross-coupling in flow using supported catalysts: Mild, clean, efficient and sustainable suzuki-miyaura coupling in a single pass
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A mild, clean, practical, sustainable and high yielding procedure for Suzuki-Miyaura cross-coupling in a single pass using a silica-supported palladium catalyst is described. The catalyst can be used in more than 30 reactions and for more than 8 h of continuous processing without a decrease in reactivity due to the low leaching observed. Different halides/pseudo-halides and organoboron compounds can be used without modifying the standard procedure.
- De M. Munoz, Juan,Alcazar, Jesus,De La Hoz, Antonio,Diaz-Ortiz, Angel
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supporting information
p. 3456 - 3460
(2013/02/22)
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- An efficient palladium-benzimidazolyl phosphine complex for the Suzuki-Miyaura coupling of aryl mesylates: Facile ligand synthesis and metal complex characterization
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A new class of easily accessible hemilabile benzimidazolyl phosphine ligands has been developed. The ligand skeleton is prepared from commercially available and inexpensive o-phenylenediamine and 2-bromobenzoic acid. With catalyst loading down to 0.5 mol% palladium, excellent catalytic activity towards the Suzuki-Miyaura coupling of aryl mesylates is still observed. This represents the lowest catalyst loading achieved so far for this reaction in general. X-Ray crystallography shows that new ligand L2 is coordinated with Pd in a κ2-P,N fashion.
- Chung, Kin Ho,So, Chau Ming,Wong, Shun Man,Luk, Chi Him,Zhou, Zhongyuan,Lau, Chak Po,Kwong, Fuk Yee
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supporting information; experimental part
p. 1967 - 1969
(2012/03/10)
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- HETEROCYCLIC COMPOUNDS FOR THE INHIBITION OF PASK
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Disclosed herein are new heterocyclic compounds and compositions and their application as pharmaceuticals for the treatment of disease. Methods of inhibiting PAS Kinase (PASK) activity in a human or animal subject are also provided for the treatment of diseases such as diabetes mellitus.
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Page/Page column 118
(2012/09/21)
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- HETEROCYCLIC COMPOUNDS FOR THE INHIBITION OF PASK
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Disclosed herein are new heterocyclic compounds and compositions and their application as pharmaceuticals for the treatment of disease. Methods of inhibiting PAS Kinase (PASK) activity in a human or animal subject are also provided for the treatment of diseases such as diabetes mellitus.
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Page/Page column 25
(2012/09/11)
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- Synthesis of amido-N-imidazolium salts and their applications as ligands in suzuki-miyaura reactions: Coupling of hetero- aromatic halides and the synthesis of milrinone and irbesartan
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A new catalytic system based on palladium-amido-N-heterocyclic carbenes for Suzuki-Miyaura coupling reactions of heteroaryl bromides is described. A variety of sterically bulky, amido-N-imidazolium salts were synthesized in high yields from the corresponding anilines. This catalytic system effectively promoted Suzuki-Miyaura couplings of heteroaryl bromides and chlorides with a range of boronic acids to give the corresponding aryl compounds in high yield. The yield was increased with increasing steric bulkiness of the substituted group. Especially, 1-(2,6-diisopropylphenyl)-3-N-(2,4,6-tri-tert- butylphenylacetamido)imidazolium bromide (4bc) exhibited 850,000 TON in the coupling reaction of 2-bromopyridine and phenylboronic acid. In addition, pharmaceutical compounds such as milrinone and irbesartan were synthesized via Suzuki-Miyaura coupling using sterically bulky, amido-N-imidazolium salt (4bc) as a ligand. Copyright
- Kumar, Manian Rajesh,Park, Kyungho,Lee, Sunwoo
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supporting information; experimental part
p. 3255 - 3266
(2011/02/23)
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- Cationic gold(I)-mediated intramolecular cyclization of 3-alkyne-1,2-diols and 1-amino-3-alkyn-2-ols: A practical route to furans and pyrroles
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The intramolecular cyclizations of the 3-alkyne-1,2-diols and the 1-amlno-3-alkyn-2-ols with a low catalyst loading (0.05-0.5 mol %) of (Ph 3P)AuCl - AgNTf2 or (Ph3P)AuCl-AgOTf proceeded at room temperature to provide a variety of substituted furans and pyrroles In excellent yields (85-98% yields). This method Is also fully applicable to the conversion of several dozen grams of the substrate using only 0.05 mol % each of the Au and Ag catalysts.
- Egi, Masahiro,Azechi, Kenji,Akai, Shuji
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supporting information; experimental part
p. 5002 - 5005
(2009/12/26)
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- PYRROLE ANTIFUNGAL AGENTS
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The invention provides compounds of formula (I), and pharmaceutically and agriculturally acceptable salts thereof; wherein: R1, R2, R3, R4, R5, R6, A1, L1 and n are as defined herein. These compounds and their pharmaceutically acceptable salts are useful in prevention or treatment of a fungal disease. Compounds of formula (I), and agriculturally acceptable salts thereof, may also be used as agricultural fungicides.
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Page/Page column 142-143
(2009/12/05)
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- Palladium/tetraphosphine catalyzed suzuki cross-coupling of heteroarylboronic acids with aryl halides
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(Chemical Equation Presented) cis,cis,cis-1,2,3,4- Tetrakis(diphenylphosphinomethyl)cyclopentane/[PdCl(C3H 5)]2 efficiently catalyses the Suzuki reaction of heteroarylboronic acids with aryl bromides and also the coupling of arylboronic acids with heteroaryl bromides. The coupling of thiophene- or benzothiopheneboronic acids, furan- or benzofuranboronic acids and 3-pyridineboronic acid with a variety of aryl bromides gave the corresponding coupling products in good yields. However, in most cases, better results in terms of ratio substrate/catalyst were obtained for the reverse reaction using heteroaryl bromides with arylboronic acids.
- Kondolff, Isabelle,Doucet, Henri,Santelli, Maurice
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p. 109 - 118
(2008/09/18)
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- A metathesis approach to aromatic heterocycles
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The ring closing metathesis (RCM) reaction can be used to prepare substituted furans and pyrroles. By utilising a Pd-catalysed coupling reaction with methoxyallene, allylic alcohols and sulfonamides can be converted into substrates that are ideal precursors to ring closing metathesis. After the RCM reaction is complete, the addition of acid promotes an elimination of methanol to form the fully aromatised system. A range of different substitution patterns and functional groups are compatible with this sequence. Double allene coupling, RCM and elimination reactions are also possible and allow the formation of biaryl systems. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005.
- Donohoe, Timothy J.,Orr, Allan J.,Gosby, Katherine,Bingham, Matilda
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p. 1969 - 1971
(2007/10/03)
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- Suzuki coupling reactions of heteroarylboronic acids with aryl halides and arylboronic acids with heteroaryl bromides using a tetraphosphine/palladium catalyst
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cix,cis,cis-1,2,3,4-Tetrakis(diphenylphosphinomethyl)cyclopentane/ [PdCl(C3H5)]2 efficiently catalyses the Suzuki reaction of heteroarylboronic acids with aryl bromides and also the coupling of arylboronic acids with heteroaryl bromides. The coupling of thiopheneboronic acids, 3-furanboronic acid and 3-pyridineboronic acid with a variety of aryl bromides gave the corresponding adducts in good yields. However, in most cases, better results in terms of substrate/catalyst ratio were obtained for the reaction of heteroaryl bromides with arylboronic acids. Georg Thieme Verlag Stuttgart.
- Kondolff, Isabelle,Doucet, Henri,Santelli, Maurice
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p. 2057 - 2061
(2007/10/03)
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- Regioselective ortho lithiation of 3-aryl and 3-styryl furans
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(Chemical Equation Presented) An unusual regioselectivity pattern for the ortho lithiation of 3-aryl and 3-styryl furans has been uncovered wherein lithiation occurs preferentially at the sterically encumbered 2-position. The results are attributed, at le
- Tofi, Maria,Georgiou, Thomas,Montagnon, Tamsyn,Vassilikogiannakis, Georgios
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p. 3347 - 3350
(2007/10/03)
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- New synthesis of biaryls via Rh-catalyzed decarbonylative Suzuki-coupling of carboxylic anhydrides with arylboroxines
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The catalytic cross-coupling of aromatic carboxylic anhydrides or acid chlorides with triarylboroxines has been achieved for the first time under decarbonylation, giving rise to the unsymmetrical biaryls rather than the expected diaryl ketones. This new decarbonylative Suzuki coupling, catalyzed by a [Rh(ethylene)2Cl]2/KF system, can be applied to aromatic, heteroaromatic and vinylic carboxylic anhydrides, potentially opening up new perspectives for the use of carboxylic acid derivatives as substrates in biaryl syntheses.
- Goossen,Paetzold
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p. 1665 - 1668
(2007/10/03)
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- Palladium-catalyzed Suzuki-Miyaura cross-coupling reactions of potassium aryl- and heteroaryltrifluoroborates
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An extended study of the reactivity of potassium aryl- and heteroaryltrifluoroborates in Suzuki-Miyaura cross-coupling reactions is presented. The coupling of aryl- and electron-rich heteroaryltrifluoroborates with aryl and activated heteroaryl bromides proceeds readily under ligandless conditions. When deactivated aryl- and heteroaryltrifluoroborates are coupled with aryl and heteroaryl bromides and chlorides, a low loading (0.5-2%) of PdCl2(dppf)·CH2Cl2 efficiently catalyzes the reactions. Under either condition, reactions can generally be carried out in an open atmosphere.
- Molander, Gary A.,Biolatto, Betina
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p. 4302 - 4314
(2007/10/03)
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- An expedient palladium-mediated route to 3-arylfurans
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A facile route to 3-arylfurans has been developed by employing the Heck reaction between 2,5-dihydro-2,5-dimethoxyfuran and aryl iodides as the key step.
- Taniguchi, Takahiko,Nagata, Hiroshi,Kanada, Regina Mikie,Kadota, Kohei,Takeuchi, Miwako,Ogasawara, Kunio
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- Metalloproteinase inhibitors, pharmaceutical compositions containing them, and their use
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The present invention is directed to compound of the formula I: STR1 wherein R1, R2, R3, R4, R5, X, Y, and STR2 are as defined herein. These compounds are useful for inhibiting the activity of a metalloproteinase by contacting the metalloproteinase with an effective amount of the inventive compounds.
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- Design and Synthesis of Novel and Potent Monoamine Oxidase Inhibitors
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Reversible and selective monoamine oxidase-A inhibitors (RIMA's) like moclobemide (Aurorix) have rehabilitated the use of MAO inhibitors as drugs of choice in depression.Starting from the structure of moclobemide, we tried to identify novel
- Branca, Quirico,Jakob-Roetne, Roland,Kettler, Rolf,Roever, Stephan,Scalone, Michelangelo
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p. 381 - 385
(2007/10/03)
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- Regiospecific synthesis of 3,4-disubstituted furans and 3-substituted furans using 3,4-bis(tri-n-butylstannyl)furan and 3-(tri-n-butylstannyl)furan as building blocks
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3,4-Bis(tri-n-butylstannyl)furan and 3-(tri-n-butylstannyl)furan have been prepared and used successfully as building blocks to lead to various 3,4-disubstituted furans and 3-substituted furans, respectively.
- Yang,Wong
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p. 9583 - 9608
(2007/10/02)
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- Preparation of α-Hydroxy-γ-lactones and their Application in the Synthesis of α,β-Butenolides, α-Alkylidene-γ-lactones and Furans
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A straightforward synthesis of α-hydroxy-γ-butyrolactones was carried out by condensation reaction of the lithium anion of ethoxyethyl-protected cyanohydrins with epoxides, followed by acidic treatment.Synthetic applications of these synthons in the preparation of interesting α,β-butenolides, α-alkylidene-γ-lactones and furans are described.
- Munoz, A. Heber,Tamariz, Joaquin,Jimenez, Rogelio,Mora, Gustavo Garcia de la
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p. 501 - 522
(2007/10/02)
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- SYNTHESIS OF FURANS BY CARBENE INSERTION
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reactions of α,α-dimethoxy ketones with diethyl diazomethylphosphonate proceed initially to dihydrofurans, probably through C-H insertion of a carbene intermediate; subsequent elimination of methanol affords the corresponding furans in good overall yields
- Buxton, Sheila R.,Holm, Kjetil H.,Skattebol, Lars
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p. 2167 - 2168
(2007/10/02)
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- Reactions of α-Oxo Ketene Dithioacetals with Dimethylsulfonium Methylide: A New Versatile Synthesis of Furans and Butenolides
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The reaction of 1-mono- and 1,2-disubstituted 3,3-bis(methylthio)-2-propen-1-ones 1 with dimethylsulfonium methylide (2) affords 2,2-bis(methylthio)-2,5-dihydrofurans 3 via epoxide 8 which can be isolated in a special case.A couple of methods including acid treatment effected the conversion of 3 to 2-(methylthio)furans 4, which are found to be useful synthons of a variety of furans and butenolides.Two naturally occurring furans, perillene and rosefuran, were synthesized by this method.
- Okazaki, Renji,Negishi, Yoshio,Inamoto, Naoki
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p. 3819 - 3824
(2007/10/02)
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- SYNTHESIS OF 1-METHOXY-2-OXOALKYL PHENYL SULFIDES AND THEIR SYNTHETIC APPLICATION TO 3-SUBSTITUTED FURANS
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1-Methoxy-2-oxoalkyl phenyl sulfides were newly synthesized from methoxy(phenylthio)methane and various N,N-dimethylalkanamides.Synthetic application of the compounds thus obtained to several 3-substituted furans also is reported.
- Mandai, Tadakatsu,Takeshita, Masahiro,Mori, Kazuhito,Kawada, Mikio,Otera, Junzo
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p. 1909 - 1910
(2007/10/02)
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- A REGIOSPECIFIC SYNTHESIS OF CARBOSUBSTITUTED HETEROAROMATIC DERIVATIVES VIA Pd-CATALYZED CROSS COUPLING
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The Pd-catalyzed cross-coupling reaction of either heteroarylzinc derivatives with unsaturated organic halides or heteroaryl halides with organometallic reagents containing Zn or Al can produce cleanly and regiospecifically the corresponding carbo-substituted heteroatomic compounds in high yields.
- Negishi, Ei-ichi,Luo, Fen-Tair,Frisbee, Roger,Matsushita, Hajime
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p. 117 - 122
(2007/10/02)
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