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A novel synthesis of chiral tetrahydroisoquinolines employing silyl enol ethers in the presence of chiral acyl chlorides

6,7-Dimethoxyisoquinoline derivatives reacted with silyl enol ethers in a highly diastereoselective manner in the presence of an acyl chloride derived from L-alanine. (-)-Homolaudanosine was synthesized in an enantiopure form from 6,7-dimethoxyisoquinoline via six steps using this method.

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Cu- and Mo-catalysed expedient synthesis of alkynyl-substituted derivatives of 1,2-dihydropyridines, -quinolines and -isoquinolines

An efficient synthesis of 1,2-dihydroisoquinolines and -quinolines by employing dimethyl acetylenedicarboxylate activated isoquinolines and quinolines in conjuction with the CuC12/Et3N catalytic system is described herein. Furthermore, the MoO3-catalysed alkynylation of pyridines and substituted pyridines has also been achieved. Moreover, this process has allowed the rapid synthesis of alkynyl derivatives of dihydroisoquinoline and -quinoline with functional group variations of the alkynyl group by using a low catalyst loading (i.e., 1 mol-%).

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1532-97-4, Name is 4-Bromoisoquinoline, belongs to isoquinoline compound, is a common compound. COA of Formula: C9H6BrNIn an article, once mentioned the new application about 1532-97-4.

Synthesis of primary amides by aminocarbonylation of aryl/hetero halides using non-gaseous NH3 and CO sources

Abstract A practically simple method for the synthesis of primary amides via the palladium-catalysed aminocarbonylation of aromatic halides by using solid sources of gaseous ammonia and carbon monoxide is described. The system tolerated a wide variety of hindered and functionalized aryl/hetero halides and afforded good to excellent yields (69-94%) of the amide. Pharmacologically active Exalamide and Pyrazinecarboxamide were synthesised in high yields to demonstrate the effectiveness of this method.

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Copper-catalyzed hydrolysis of bromoisoquinolines: Preparation of hydroxyisoquinolines

A complex phenomenon was observed in the process of preparing hydroxyisoquinoline through copper-catalyzed hydrolysis of bromoisoquinoline. The copper (II) complexes of hydroxyisoquinoline (L2Cu.5H2O) were characterized by high resolution mass spectra, thermogravimetric analysis, IR, 1H nuclear magnetic resonance (NMR), and 2D-NMR. The Cu (II) complexes were mononuclear and coordinated with oxygen and nitrogen atom of two hydroxyisoquinoline and five water molecules in which a strong hydrogen bond was present. Two optimized methods had been studied to prevent the formation of copper (II) complexes. The isoquinoline with 4, 5, 6, 7, and 8 hydroxyl substitutions were successfully prepared by copper-catalyzed hydrolysis of corresponding bromoisoquinoline and then workup by sodium sulfide or adjusted pH by dry ice or carbon dioxide gas.

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Isoquinoline thromboxane synthetase inhibitors

4-[(4-Isoquinolinylmethyl)amino]benzoic acid derivatives useful as selective thromboxane synthetase inhibitors are described herein. The compounds are obtained from the appropriate 4-isoquinolinecarboxylic acid derivative and an aminobenzoic acid derivative. This gives the corresponding Schiff base which is then reduced to give the desired compounds.

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Palladium-catalyzed direct arylation of pyrazole derivatives: A green access to 4-arylpyrazoles

1,3,5-Trisubstituted pyrazoles were found to be suitable partners for palladium-catalyzed direct arylation via C-H activation/functionalization using aryl bromides. The reaction conditions and the catalyst have a determining influence on the yields. The system using palladium(II) acetate as the catalyst, potassium acetate as the base, and N,N-dimethylacetamide as the solvent promotes selective 4-arylations in moderate to high yields. Several aryl and heteroaryl bromide derivatives have been employed successfully; their electronic properties have a decisive influence on the yields of coupling products. Electron-poor aryl bromides gave satisfactory results, whereas the electron-rich ones gave lower yields. Georg Thieme Verlag Stuttgart – New York.

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DMSO-Ac2O promoted nitration of isoquinolines. One-step synthesis of 1-nitroisoquinolines under mild conditions

1-Nitroisoquinolines were directly prepared from the corresponding isoquinolines with potassium nitrite and acetic anhydride in DMSO in good yields.

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Synthesis of Aza-Heteroaromatic Dithiocarbamates via Cross-Coupling Reactions of Aza-Heteroaromatic Bromides with Tetraalkylthiuram Disulfides

The preparation of various aza-heteroaromatic dithiocarbamates from aza-heteroaromatic bromides and tetraalkylthiuram disulfides is reported. The transformation provides a convenient procedure, with good yields and functional group tolerance to various important nitrogen-containing heteroaromatic dithiocarbamates such as benzothiazole, quinoline, pyridine, and pyrazine motifs. This protocol allows the facile synthesis of some potential biologically active compounds.

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Ligand-free-palladium-catalyzed direct 4-arylation of isoxazoles using aryl bromides

4-rylisoxazoles can be easily prepared by a palladium-catalysed C-H bond activation/arylation of 3,5-disubstituted isoxazoles using aryl or heteroaryl bromides. Good yields were generally obtained by using 0.1-0.5 mol-% of the airstable PdCl2 complex as the catalyst. A range of functional groups such as acetyl, formyl, ester, fluoro, nitro, trifluoro-methyl or nitrile on the aryl bromide is tolerated. This reaction is environmentally attractive, as the major waste is KBr/ AcOH instead of the metallic salts arising from classical cross-coupling procedures,

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Modular ipso/ ortho Difunctionalization of Aryl Bromides via Palladium/Norbornene Cooperative Catalysis

Palladium/norbornene (Pd/NBE) cooperative catalysis has emerged as a useful tool for preparing poly substituted arenes; however, its substrate scope has been largely restricted to aryl iodides. While aryl bromides are considered as standard substrates for Pd-catalyzed cross coupling reactions, their use in Pd/NBE catalysis remains elusive. Here we describe the development of general approaches for aryl bromide-mediated Pd/NBE cooperative catalysis. Through careful tuning the phosphine ligands and quenching nucleophiles, ortho amination, acylation and alkylation of aryl bromides have been realized in good efficiency. Importantly, various heteroarene substrates also work well and a wide range of functional groups are tolerated. In addition, the utility of these methods has been demonstrated in sequential cross coupling/ortho functionalization reactions, consecutive Pd/NBE-catalyzed difunctionalization to construct penta-substituted aromatics and two-step meta functionalization reactions. Moreover, the origin of the ligand effect in ortho amination reactions has been explored through DFT studies. It is expected that this effort would significantly expand the reaction scope and enhance the synthetic potential for Pd/NBE catalysis in preparing complex aromatic compounds.

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