1131-63-1Relevant articles and documents
Evidence for aromatic ring reduction in the biodegradation pathway of carboxylated naphthalene by a sulfate reducing consortium
Zhang, Xiaoming,Sullivan, Elise R.,Young
, p. 117 - 124 (2000)
Naphthalene was used as a model compound in order to study the anaerobic pathway of polycyclic aromatic hydrocarbon degradation. Previously we had determined that carboxylation is an initial step for anaerobic metabolism of naphthalene, but no other intermediate metabolites were identified (Zhang & Young 1997). In the present study we further elucidate the pathway with the identification of six novel naphthalene metabolites detected when cultures were fed naphthalene in the presence of its analog 1-fluoronaphthalene. Results from cultures supplemented with either deuterated naphthalene or non-deuterated naphthalene plus [13C]bicarbonate confirm that the metabolites originated from naphthalene. Three of these metabolites were identified by comparison with the following standards: 2-naphthoic acid (2-NA), 5,6,7,8-tetrahydro-2-naphthoic acid, and decahydro-2-naphthoic acid. The presence of 5,6,7,8-tetrahydro-2-NA as a metabolite of naphthalene degradation indicates that the first reduction reaction occurs at the unsubstituted ring, rather than the carboxylated ring. The overall results suggest that after the initial carboxylation of naphthalene, 2-NA is sequentially reduced to decahydro-2-naphthoic acid through 5 hydrogenation reactions, each of which eliminated one double bond. Incorporation of deuterium atoms from D20 into 5,6,7,8-tetrahydro-2-naphthoic acid suggests that water is the proton source for hydrogenation.
Carboxylation of Aryl Triflates with CO2 Merging Palladium and Visible-Light-Photoredox Catalysts
Bhunia, Samir Kumar,Das, Pritha,Nandi, Shantanu,Jana, Ranjan
supporting information, p. 4632 - 4637 (2019/06/27)
We report herein a visible-light-promoted, highly practical carboxylation of readily accessible aryl triflates at ambient temperature and a balloon pressure of CO2 by the combined use of palladium and photoredox Ir(III) catalysts. Strikingly, the stoichiometric metallic reductant is replaced by a nonmetallic amine reductant providing an environmentally benign carboxylation process. In addition, one-pot synthesis of a carboxylic acid directly from phenol and modification of estrone and concise synthesis of pharmaceutical drugs adapalene and bexarotene have been accomplished via late-stage carboxylation reaction. Furthermore, a parallel decarboxylation-carboxylation reaction has been demonstrated in an H-type closed vessel that is an interesting concept for the strategic sector. Spectroscopic and spectroelectrochemical studies indicated electron transfer from the Ir(III)/DIPEA combination to generate aryl carboxylate and Pd(0) for catalytic turnover.
Direct carboxylation of simple arenes with CO2 through a rhodium-catalyzed C-H bond activation
Suga, Takuya,Mizuno, Hajime,Takaya, Jun,Iwasawa, Nobuharu
supporting information, p. 14360 - 14363 (2015/02/19)
Direct carboxylation of simple arenes under atmospheric pressure of CO2 is achieved through a rhodium-catalyzed C-H bond activation without the assistance of a directing group. Various arenes such as benzene, toluene, xylene, electron-rich or electron-deficient benzene derivatives, and heteroaromatics are directly carboxylated with high TONs. This journal is
HCV PROTEASE INHIBITORS
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Page/Page column 37-38, (2008/12/07)
This invention relates to the compounds of formula (I) shown below. Each variable in formula (I) is defined in the specification. These compounds can be used to treat hepatitis C virus infection.
A PROCESS FOR THE PREPARATION OF 3-CYANO-1-NAPHTHOIC ACID AND SOME ANALOGUES THEREOF
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Page 22, (2010/02/05)
The present invention is related to a process for the preparation of 3-cyano-1-naphthoic acid and some analogues thereof of formula (1), the intermediate 1-halo-3-cyano naphthalene and some analogues thereof used in this process and a process for the preparation of said intermediate.
Quaternary ammonium compounds as tachykinin antagonists
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, (2008/06/13)
The present invention provides a compound of formula (I) wherein R is phenyl, C3-C7cycloalkyl or heteroaryl, each of which being optionally benzo- or C3-C7cycloalkyl-fused and optionally substituted, including in the benzo- or C3-C7cycloalkyl-fused portion, by from 1 to 3 substituents each independently selected from C1-C4alkyl, fluoro(C1-C4)alkyl, C1-C4alkoxy, fluoro(C1-C4)alkoxy, phenoxy, C2-C4alkanoyl, halo, C1-C4alkoxycarbonyl, C3-C7cycloalkyl, —S(O)m(C1-C4alkyl), cyano, —NR2R3, —S(O)mNR2R3, —NR4(C1-C4alkanoyl) and —CONR2R3, or R is 2,3-dihydrobenzo[b]furanyl or chromanyl; R1is H or C1-C6alkyl; W is a direct link, methylene or ethylene; X is unbranched C2-C4alkylene; Y is phenyl, naphthyl, benzyl, pyridyl, thienyl or C3-C7cycloalkyl, each of which being optionally substituted by from 1 to 3 substituents each independently selected from C1-C4alkyl, fluoro(C1-C4)alkyl, C1-C4alkoxy, fluoro(C1-C4)alkoxy, halo and cyano; Ar is phenyl, naphthyl, benzyl, thienyl, benzo[b]thienyl or indolyl, each of which being optionally substituted by from 1 to 3 substituents each independently selected from C1-C4alkyl, fluoro(C1-C4)alkyl, C1-C4alkoxy, fluoro(C1-C4)alkoxy, halo and cyano, or Ar is 1,3-benzodioxolan-4 or 5-yl or 1,4-benzodioxan-5 or 6-yl; ZAis a pharmaceutically acceptable anion; with the proviso that when W is a direct link and R is optionally fused and optionally substituted heteroaryl, said heteroaryl is linked by a ring carbon atom to the carbonyl group. The compounds are tachykinin antagonists.
Nickel Catalysed Conversion of Phenol Triflates into Aromatic Nitriles and Acids
Chambers, Mark R. I.,Widdowson, David A.
, p. 1365 - 1366 (2007/10/02)
Phenols, as their trifluoromethanesulphonate (triflate) esters, are converted by potassium cyanide in the presence of catalytic tetrakistriphenylphosphinenickel(0) into the corresponding nitriles, thence to the carboxylic acids.
Aromatic Spiranes, XVI: Syntheses of Mono- and Dianellated 2,2'-Spirobiindane-1,1'diones
Neudeck, Horst K.
, p. 597 - 622 (2007/10/02)
The spiroketones 19, 21, 24, 27, and 31 were prepared by cyclisation of the dicarboxylic acids and their acid chlorides, resp., (18, 20, 22, 23, 25, 26, 28, and 30) with polyphosphoric acid (PPA) or SnCl4.The latter compounds were synthesized by alkylation of the appropriate β-keto esters 10, 11, 12, and 13 with the "benzyl chlorides" 14, 15, 16, and subsequent retro-Claisen reaction.The spiro compounds 21a and 39 were obtained by PPA-cyclisation of the keto acids 35 and 38, which in turn were prepared by aldol-reaction of the ketones s-hydrindacen-1-on and 9a with phthalaldehydic acid to the olefinic keto acids 33 and 36 followed by catalytic hydrogenation. - Keywords: Indane-1-one; s-Hydrindacene-1-one; Tetrahydrobenzoindane-1-one; β-Keto esters; Phthalaldehydic acid; Spiro cyclisation; 2,2'-Spirobiindane-1,1'-diones; 1H-nmr spectra; Mass spectra
Inverse Electron Demand Diels-Alder Reactions of 3-Carbomethoxy-2-pyrones. Controlled Introduction of Oxygenated Aromatics: Benzene, Phenol, Catechol, Resorcinol, and Pyrogallol Annulation. Regiospecific Total Synthesis of Sendaverine and a Preparation of 6,7-Benzomorphans
Boger, Dale B.,Mullican, Michael D.
, p. 4033 - 4044 (2007/10/02)
A full investigation of the preparation and Diels-Alder reactions of 3-carbomethoxy-2-pyrones is described.Methods for the preparation of a full range of oxygen-substituted aromatics: benzene, 1-, 2-, or 3-phenol, symmetrical or unsymmetrical o-catechol, resorcinol, and pyrogallol annulation from a common 3-carbomethoxy-2-pyrone intermediate are detailed.A regiospecific total synthesis of sendaverine, a 2-benzyltetrahydroisoquinoline possessing a selectively protected, symmetrical o-catechol, and a preparation of 6,7-benzomorphans are described.
