- Gold vs Rhodium Catalysis: Tuning Reactivity through Catalyst Control in the C-H Alkynylation of Isoquinolones
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A site-selective C-4/C-8 alkynylation of isoquinolones catalyzed by gold and rhodium complexes is reported. A broad range of synthetically useful functional groups (-F, -Cl, -Br, -CF3, -OMe, alkyl, etc.) were tolerated, providing an efficient a
- Shaikh, Aslam C.,Shinde, Dinesh R.,Patil, Nitin T.
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- Palladium complexes with an annellated mesoionic carbene (MIC) ligand: Catalytic sequential Sonogashira coupling/cyclization reaction for one-pot synthesis of benzofuran, indole, isocoumarin and isoquinolone derivatives
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Two Pd(ii) complexes (1 and 2) featuring a fused π-conjugated imidazo[1,2-a][1,8]naphthyridine-based mesoionic carbene ligand have been synthesized and structurally characterized. Both complexes effectively catalyze the one-pot synthesis of benzofuran starting from phenylacetylene and 2-iodophenol under mild conditions. Complex 1 is found to be an excellent catalyst for the straightforward access to a library of benzofuran, indole, isocoumarin and isoquinolone derivatives by the reaction of terminal alkynes with 2-iodo derivates of phenol, N-methyl aniline, benzoic acid and N-methyl benzamide, respectively. The general utility of the catalytic method is demonstrated using a variety of diversely substituted terminal alkynes and the corresponding desired products are obtained in good to excellent yields. On the basis of control experiments, a two-cycle mechanism is proposed which involves the Sonogashira coupling of 2-iodo derivatives with alkynes and the subsequent cyclization of the corresponding 2-alkynyl compounds.
- Bera, Jitendra K.,Daw, Prosenjit,Reshi, Noor U Din,Tyagi, Akshi
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supporting information
p. 15238 - 15248
(2020/11/18)
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- An organocatalyst bound α-aminoalkyl radical intermediate for controlled aerobic oxidation of iminium ions
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A catalyst bound α-aminoalkyl radical intermediate from iminium is developed to control its formation and reactivity with aerobic oxygen. The influence of the catalyst was demonstrated via the ease of radical intermediate formation and its subsequent reactivity, including the first catalyst-controlled enantioselective aerobic oxidation with a chiral phosphite catalyst.
- Motaleb, Abdul,Bera, Asish,Maity, Pradip
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p. 5081 - 5085
(2018/07/29)
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- Catalytic Intramolecular Wittig Reaction Based on a Phosphine/Phosphine Oxide Catalytic Cycle for the Synthesis of Heterocycles
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The catalytic intramolecular Wittig reactions of carbonyl-containing bromides are reported. The R3PO byproducts participate in the catalytic cycle; therefore, the Wittig reaction can be accomplished with only a catalytic amount of organophosphorus reagent. The reaction has also been applied to the efficient and selective synthesis of isoquinolin-1(2H)-ones, indoles, 2,3-dihydro-1H-2-benzazepin-1-ones, benzofurans, and 1,2-dihydroquinolines with a catalytic amount of phosphine oxide (0.1 equiv.) and a tetramethyldisiloxane/titanium isopropoxide [TMDS/Ti(OiPr)4] reductant system (yields: 35–88 %).
- Wang, Long,Sun, Mei,Ding, Ming-Wu
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p. 2568 - 2578
(2017/05/19)
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- Method of catalyzing tandem reaction to synthesize isoquinolinone derivative in water phase
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The invention provides a method of catalyzing tandem reaction to synthesize isoquinolinone derivative in water phase. In the method, the isoquinolinone derivative is synthesized in a one-pot manner that on the basis of 1 mol of 0.1-1 mol/L ortho-halogenated benzamide and 0.1-5 mol of a terminal alkyne, a reaction is carried out in a water phase under the effect of 0.001-1 mol of bivalent copper salt and phenanthroline catalysts in the presence of 0.5-6 mol of inorganic alkali or organic alkali, reaction temperature being 20-160 DEG C and reaction time being 1-50 h. In the method, the bivalent copper salt and phenanthroline can catalyze the reaction between the ortho-halogenated benzamide and the terminal alkyne in the water phase, wherein water serves as a solvent, so that the method is environment-friendly, and avoids usage of noble metals, high temperature reaction and the like reaction conditions. The method has simple operations and high yield, is safe and low-cost, is low in pollution and is suitable for various functional groups.
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Paragraph 0025-0026; 0051-0052; 0055-0076; 0081-0084;
(2017/05/19)
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- Catalyst Controlled Divergent C4/C8 Site-Selective C-H Arylation of Isoquinolones
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The catalyst-controlled C4/C8 site-selective C-H arylation of isoquinolones using aryliodonium salts as the coupling partners was developed. The C4-selective arylation was successfully achieved via an electrophilic palladation pathway. A completely differ
- Lee, Soyoung,Mah, Shinmee,Hong, Sungwoo
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supporting information
p. 3864 - 3867
(2015/08/18)
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- Transition metal-free cascade reactions of alkynols to afford isoquinolin-1(2H)-one and dihydroisobenzofuran derivatives
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Transition metal-free cascade reactions of alkynols with imines have been achieved using potassium tert-butoxide as catalyst. Switching the reaction solvent gives two kinds of products in good yield: isoquinolin-1(2H)-one derivatives and dihydroisobenzofuran derivatives. This approach was used to generate the natural product 8-oxypseudopalmatine in a two-step procedure from commercially available starting materials. Additionally, multicomponent reactions of alkynols, aldehydes, and amines were also successfully achieved to afford isoquinolin-1(2H)-one derivatives.
- Li, Deng Yuan,Shi, Ke Ji,Mao, Xiao Feng,Chen, Guo Rong,Liu, Pei Nian
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p. 4602 - 4614
(2014/06/09)
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- Solvent-switched benzylic methylene functionalization: Addition, ring-opening, cyclization, and unexpected cleavage of C-O and C-C bonds
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Intermolecular benzylic methylene functionalization of exo-cyclic enol ethers has been achieved using imines as reagents and potassium tert-butoxide as the catalyst. Depending on the solvent used, the reaction proceeds by two pathways. In THF, an addition
- Li, Deng Yuan,Shang, Xue Song,Chen, Guo Rong,Liu, Pei Nian
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supporting information
p. 3848 - 3851
(2013/09/02)
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- Palladium-Catalyzed Synthesis of Isoquinolinones via Sequential Cyclization and N-O Bond Cleavage of N -Methoxy- o -alkynylbenzamides
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A palladium-catalyzed controlled 6-endo-dig cyclization process has been developed for the chemoselective synthesis of isoquinolin-1-ones from N-alkoxy-o-alkynylbenzamides. The mechanism and scope of the reaction have also been investigated. Deuterium-labeling studies were used to confirm the intramolecular 1,5-hydrogen shift as a key step in the transformation. Georg Thieme Verlag Stuttgart · New York.
- Jithunsa, Manita,Ueda, Masafumi,Aoi, Naoki,Sugita, Shoichi,Miyoshi, Tetsuya,Miyata, Okiko
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p. 475 - 478
(2013/03/29)
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- Synthesis of functionalized isoquinolin-1(2H)-ones by copper-catalyzed α-arylation of ketones with 2-halobenzamides
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Copper is key: A concise route to isoquinolin-1(2H)-ones from simple and readily available starting materials is provided by an efficient copper-catalyzed annulation of ketones with 2-halobenzamides. The method is applicable to a wide range of ketones con
- Shi, Yan,Zhu, Xuebin,Mao, Haibin,Hu, Hongwen,Zhu, Chengjian,Cheng, Yixiang
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supporting information
p. 11553 - 11557
(2013/09/12)
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- Synthesis of 12-oxobenzo[c]phenanthridinones and 4-substituted 3-arylisoquinolones via Vilsmeier-Haack reaction
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Vilsmeier-Haack reaction on 3-arylisoquinolones resulted in versatile 4-formylated 3-arylisoquinolones that were further derivatized into 12-oxobenzo[c]phenanthridinones, 4-alkoxymethyl-3-arylisoquinolones, 3-aryl-4-phenoxymethylisoquinolones, 4-aminometh
- Khadka, Daulat Bikram,Yang, Su Hui,Cho, Suk Hee,Zhao, Chao,Cho, Won-Jea
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p. 250 - 261
(2012/01/05)
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- A CuBr-mediated aerobic reaction of 2-alkynylbenzaldehydes and primary amines: Synthesis of 4-bromoisoquinolones
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A method for synthesis of 4-bromoisoquinolones has been developed starting from 2-alkynylbenzaldehydes and primary amines mediated by CuBr under an O 2 atmosphere, where CuBr plays multiple roles to facilitate the present reactions.
- Too, Pei Chui,Chiba, Shunsuke
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p. 7634 - 7636
(2012/09/25)
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- Synthesis, x-ray structure and photo chemistry of 2-(methyl(1-phenylvinyl) carbamoyl)phenyl acetate
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2-(Methyl(1-phenylvinyl)carbamoyl)phenyl acetate (SM), empirical formula C18H17NO3, crystallizes in the triclinic space group, P-1, with unit cell parameters α= 9.10870(10) A , b = 10.56940(10) A , c = 16.1340(2) A , a = 7
- Dehury, Sujit Kumar
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p. 214 - 221
(2012/07/14)
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- X-ray crystal structure and photo chemistry of N-methyl-N-(1-phenylvinyl) benzamide
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N-methyl-N-(1-phenylvinyl)benzamide (I) has empirical formula C16H15NO, crystallizes in the monoclinic space group, P21/n, with unit cell parameters a = 8.9101(2) A , b = 15.1416(4) A , c = 9.7737(2) A , α = 90°, β = 109.3320(10)°, c = 90°, Z = 4. Interes
- Dehury, Sujit Kumar
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p. 1386 - 1390
(2012/02/05)
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- Regiochemistry in aryl radical cyclisations (5-exo versus 6-endo) of N-vinylic 2-iodobenzamides
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Bu3SnH-mediated aryl radical cyclisations of a range of N-vinylic 2-iodobenzamides 10 were examined. The enamides 10a-d gave exclusively the 5-exo cyclisation products 11a-d, whereas the enamides 10e,f having a phenyl substituent on the vinylic carbon ato
- Ishibashi, Hiroyuki,Ohata, Kohei,Niihara, Michiyo,Sato, Tatsunori,Ikeda, Masazumi
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p. 547 - 554
(2007/10/03)
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- Fluoride ion-induced cyclization of o-[bis(trimethylsilyl)methyl]-N-acylbenzamide derivatives. New efficient synthesis of 2,3-differentially substituted 1(2H)-isoquinolones
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A wide variety of 2-alkyl-3-alkyl, -3-aryl and -3-heteroaryl-1(2H)-isoquinolones have been obtained by fluoride ion-induced intramolecular alkenation of o-[bis(trimethylsilyl)methyl]-N-acylbenzamide derivatives.
- Couture, Axel,Cornet, Helene,Deniau, Eric,Grandclaudon, Pierre,Lebrun, Stephane
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p. 469 - 476
(2007/10/03)
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- A NEW SYNTHETIC ROUTE TO 2-METHYL-3-(ARYL OR ALKYL)-1-OXO-1,2-DIHYDROISOQUINOLINES via AN INTRAMOLECULAR WITTIG REACTION
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2-Methyl-3-(aryl or alkyl)-1-oxo-1,2-dihydroisoquinolines 6a-g have been prepared via an intramolecular Wittig olefination reaction from the N-acyl-N-methyl-o-triphenylphosphoniobenzamide bromides 5a-g.
- Couture, Axel,Cornet, Helene,Grandclaudon, Pierre
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p. 3857 - 3866
(2007/10/02)
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- Intramolecular Peterson olefination of ortho-trimethylsilylmethyl-N-acyl-N-alkylbenzamides. A new route to 2-alkyl-1(2H)isoquinolones
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A variety of 2-alkyl-1(2H)isoquinolones has been efficiently synthesized by intramolecular Peterson olefination of ortho-trimethylsilylmethyl-N-acyl-N-alkylbenzamides.
- Couture, Axel,Cornet, Helene,Grandclaudon, Pierre
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- The Chemistry of Phthalide-3-carboxylic Acid. VI The Stereochemistry of Some 3-Amino(aryl)methylphthalides and the Derived 3-Aryl-4-hydroxy-3,4-dihydroisoquinolin-1(2H)-ones
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The isomeric 3-isobenzofuran-1(3H)-ones, of known configuration, have been converted into the corresponding amino and dimethylamino compounds with inversion of configuration, and hence the stereochemistry of these compounds has been
- Collins, Peter R.,Janowski, Wit K.,Prager, Rolf H.
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p. 549 - 560
(2007/10/02)
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- Cyclopalladiated Aromatic Imines in Organic Synthesis: The Preparation of Cinnamonitriles, Cinnamates, Unsymmetrical Stilbenes, Isoquinolones, and Isoquinolines
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The preparation and characterisation of some new ortho-palladiated benzaldimine complexes and their reaction with olefins are described.The reaction of di-μ-1-chloro-bis(2-alkyl-2,1-benzazapalladole) complexes (1) with styrene in trifluoroacetic acid-acetic acid mixtures yielded stilbene-2-carbaldehydes (10).These were converted into 2-methyl-3-phenyl-1(2H)-isoquinolones (12) via a mercury(II) mediated cyclisation of the N-methylimine derivatives of the stylbenes.Reaction of the complexes (1) with methyl acrylate produced methyl 2-(N-t-butyliminomethyl)cinnamates (7; Y=CO2Me) and with acrylonitril, the 2-(N-t-butyliminomethyl)cinnamonitriles (7; Y=CN), which upon in situ thermolysis gave the corresponding isoquinolines (8).
- Girling, Ian R.,Widdowson, David A.
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p. 1317 - 1324
(2007/10/02)
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- CYCLOPALLADATED IMINES IN SYNTHESIS: THE PREPARATION OF UNSYMMETRICAL STILBENES AND 3-ARYLISOQUINOLONES
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A series of cyclopalladated t-butylimines of aromatic aldehydes were reacted with styrene to give o-formylstilbenes in high yield.The N-methylimines of these were converted to 3-aryl-N-methyl-isoquinolones by oxidation with mercuric acetate.
- Girling, I. R.,Widdowson, D. A.
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p. 1957 - 1960
(2007/10/02)
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