- Visible-Light-Induced Radical Carbo-Cyclization/ gem-Diborylation through Triplet Energy Transfer between a Gold Catalyst and Aryl Iodides
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Geminal diboronates have attracted significant attention because of their unique structures and reactivity. However, benzofuran-, indole-, and benzothiophene-based benzylic gem-diboronates, building blocks for biologically relevant compounds, are unknown. A promising protocol using visible light and aryl iodides for constructing valuable building blocks, including benzofuran-, indole-, and benzothiophene-based benzylic gem-diboronates, via radical carbo-cyclization/gem-diborylation of alkynes with a high functional group tolerance is presented. The utility of these gem-diboronates has been demonstrated by a 10 g scale conversion, by versatile transformations, by including the synthesis of approved drug scaffolds and two approved drugs, and even by polymer synthesis. The mechanistic investigation indicates that the merging of the dinuclear gold catalyst (photoexcitation by 315-400 nm UVA light) with Na2CO3 is directly responsible for photosensitization of aryl iodides (photoexcitation by 254 nm UV light) with blue LED light (410-490 nm, λmax = 465 nm) through an energy transfer (EnT) process, followed by homolytic cleavage of the C-I bond in the aryl iodide substrates.
- Hashmi, A. Stephen K.,Rominger, Frank,Si, Xiaojia,Zhang, Lumin
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supporting information
p. 10485 - 10493
(2020/07/03)
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- N-(PYRIDIN-2-YLSULFONYL)CYCLOPROPANECARBOXAMIDE DERIVATIVES AND THEIR USE IN THE TREATMENT OF A CFTR MEDIATED DISEASE
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The invention relates to heterocyclic compounds of the formula (I), in which all of the variables are as defined in the specification; capable of modulating the activity of CFTR. The invention further provides a method for manufacturing compounds of the invention, and its therapeutic uses. The invention further provides methods to their preparation, to their medical use, in particular to their use in the treatment and management of diseases or disorders including Cystic fibrosis and related disorders.
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Page/Page column 249
(2020/07/14)
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- NEW COMPOUND HAVING FGFR INHIBITORY ACTIVITY AND PREPARATION AND APPLICATION THEREOF
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The present invention relates to a new compound having an FGFR inhibitory activity and preparation and application thereof. In particular, the compound according to the present invention has a structure as shown in formula I, wherein each group and substituent are as defined in the description. Also disclosed in the present invention are a preparation method for the compound and a use thereof in preparation of a drug for treating and/or preventing a tumor-related disease and/or an FGFR-related disease.
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Paragraph 0366; 0367
(2019/05/30)
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- Method for synthesizing asymmetric C-O coupled compound and application of asymmetric C-O coupled compound
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The invention discloses a method for synthesizing an asymmetric C-O coupled compound and application of the asymmetric C-O coupled compound and belongs to the technical field of chemical synthesis. According to the method, a compound represented by a form
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Paragraph 0106; 0107
(2016/10/07)
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- Exploring the potential of diarylacetylenediols as hydrogen bonding catalysts
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In the course of a search for new classes of hydrogen bonding catalysts, we have examined diarylacetylenediols as potential catalysts for the Diels-Alder reaction. General and efficient methods have been developed for the preparation of these diols. Their structures were systematically modified, and increased activity was observed for those possessing an electron-withdrawing group on the aryl groups. The electron-deficient diarylacetylenediol catalysts, while more active, undergo spontaneous cyclization to the corresponding benzo[b]furans. A mechanism is postulated to explain this facile transformation. Computational studies performed on 2-ethynylphenol help to explain the effect of the alkyne on the conformation and hydrogen bond donating ability of the adjacent OH group. Finally, the crystal structure of one of the diols is reported, and it displays an intricate network of intermolecular hydrogen bonds.
- Tuerkmen, Yunus E.,Rawal, Viresh H.
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p. 8340 - 8353
(2013/09/24)
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- Stable axial chirality in metal complexes bearing 4,4′-substituted BIPHEPs: Application to catalytic asymmetric carbon-carbon bond-forming reactions
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Not only electronic but also steric effects of 4,4′-substituents in BIPHEP derivatives and metal (Pd, Pt, and Au) complexes are shown to influence the stability of the biphenyl single bond rotation. While electron-donating or sterically demanding substituents on the 4,4′-positions destabilize the axial chirality of BIPHEP derivatives, electron-withdrawing or sterically less demanding ones on the 4,4′-positions stabilize the axis chirality. Particularly, the axial chirality of palladium dichloride complexes bearing BIPHEP with t-Bu and CF3 substituents on the 4,4′-positions is most labile and stable, respectively (ΔG≠ = 29.22 and 30.49 kcal mol-1 at 300 K; t1/2 = 7 and 56 years at 300 K). These enantiopure dicationic BIPHEPPd complexes can be employed for catalytic enantioselective arylation, alkenylation, and ene reactions to give the corresponding products in good-to-excellent yields and enantioselectivities. Significantly, in the carbonyl-ene reaction of trifluoropyruvate with isobutene, the turnover frequency (TOF) reached 58200 h-1. The remarkable effects of 4,4′-substituents in BIPHEP derivatives can be employed as a guiding principle in the design of versatile and efficient ligands.
- Aikawa, Kohsuke,Miyazaki, Yoshitaka,Mikami, Koichi
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supporting information; experimental part
p. 201 - 208
(2012/04/23)
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- HETEROCYCLIDENE-N-(ARYL)ACETAMIDE DERIVATIVE
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The blow-described formula (I): [Ch. 1] a compound represented by formula (I) : (wherein k, m, n, and p each represent 0 to 2; j and q represents 0 or 1; R1 represents a halogen atom, a hydrocarbon group, a heterocyclic group, an alkoxy group,
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Page/Page column 98
(2009/12/23)
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- Novel Heterocyclidene Acetamide Derivative
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A compound represented by formula (I′): (wherein m, n, and p each represent 0 to 2; q represents 0 or 1; R1 represents halogen, a hydrocarbon group, a heterocyclic group, an alkoxy group, an alkoxycarbonyl group, a sulfamoyl group, a CN group,
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Page/Page column 55
(2008/12/09)
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- NOVEL HETEROCYCLIDENE ACETAMIDE DERIVATIVE
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A compound represented by formula (I'): (wherein m, n, and p each represent 0 to 2; q represents 0 or 1; R1 represents halogen, a hydrocarbon group, a heterocyclic group, an alkoxy group, an alkoxycarbonyl group, a sulfamoyl group, a CN group,
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Page/Page column 80
(2010/11/30)
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- Facile preparation of 2-iodophenyl trifluoromethanesulfonates: Superior aryne precursors
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A comparative study of 3-methoxyaryne precursors revealed 2-iodo-3-methoxyphenyl triflate as the most effective in nonpolar solvent. Use of Hoppe's N-isopropyl carbamate allows for the systematic preparation of a variety of 2-iodophenyl triflates via a directed ortho-lithiation-iodination- decarbamation sequence. These steps are possible without isolation of the intermediate iodophenyl carbamates. Georg Thieme Verlag Stuttgart.
- Ganta, Ashok,Snowden, Timothy S.
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p. 2227 - 2231
(2008/02/10)
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- Synthesis of constrained arylpiperidines using intramolecular Heck or radical reactions
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Two intramolecular routes were experimented to reach the hexahydrobenzofuro[2,3-c]pyridine platform: a Heck and a radical reaction. The radical route was applicable to all substrates, whereas the Heck route was of limited use. The key adducts were obtained via a Mitsunobu condensation between halogenated phenols and an allylic alcohol, the 3-hydroxy-tetrahydropyridine.
- Morice, Christophe,Domostoj, Mathias,Briner, Karin,Mann, André,Suffert, Jean,Wermuth, Camille-Georges
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p. 6499 - 6502
(2007/10/03)
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- Synthesis of [phenyl-2-3H]-travoprost: Isopropyl ester prodrug of a selective prostaglandin FP receptor agonist
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A method for the preparation of tritium labeled travoprost, a new ocular hypotensive prostaglandin, is described. A highly selective catalytic deiodination has been identified which provides [phenyl-2-3H]-travoprost in a single synthetic step f
- Selliah, Robert,Dantanarayana, Anura,Haggard, Karen,Egan, Judith,Do, Ernest U.,May, Jesse A.
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p. 173 - 183
(2007/10/03)
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- Acetylenic phenoxypropanol derivatives and pharmaceutical compositions for the treatment of hypertension
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Phenoxypropanol derivatives having a 2-acetylenic moiety on the phenyl group thereof of the following formula (I): STR1 and their use as anti-hypertensives, e.g. in man. Also part of the invention are pharmaceutical compositions and intermediates used in
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