- Rhodium(III)-Catalyzed C-H Activation: Annulation of Petrochemical Feedstocks for the Construction of Isoquinolone Scaffolds
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We describe a simple and robust procedure for the Rh(III)-catalyzed [4+2] cycloaddition of feedstock gases enabled through C-H activation. A diverse set of 3,4-dihydroisoquinolones and 3-methylisoquinolones have been prepared in good to excellent yields.
- Barber, Joyann S.,Kong, Dehuan,Li, Wei,McAlpine, Indrawan J.,Nair, Sajiv K.,Sakata, Sylvie K.,Sun, Nicole,Patman, Ryan L.
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supporting information
p. 202 - 206
(2021/01/14)
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- Synthesis of rhodium(III)-catalyzed isoquinoline derivatives from allyl carbonates and benzimidates with hydrogen evolution
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A novel Rh(iii)-catalyzed cascade C-H activation/cyclization approach to access isoquinoline derivatives from benzimidates and available allyl carbonates with the liberation of H2 has been realized. Allyl carbonates were first used as a versati
- Dong, Lin,Li, Chao,Liu, Man,Xu, Hui-Bei,Zhang, Jing
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p. 1412 - 1416
(2020/03/03)
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- Iron-catalysed 1,2-acyl migration of tertiary α-azido ketones and 2-azido-1,3-dicarbonyl compounds
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Iron-catalysed 1,2-acyl migration of tertiary α-azido ketones and 2-azido-1,3-dicarbonyl compounds provides a simple and atom-economical approach toward enamides and isoquinolones. This paper reports two catalyst systems for these transformations which employ iron(ii) complexes [Fe(dpbz)]Br2 (dpbz = 1,2-bis(diphenylphosphino)benzene) and FeBr2/Et3N, respectively. [Fe(dpbz)]Br2 was found to be highly effective at converting 2-azido-2,3-dihydro-1H-inden-1-ones to isoquinolones. The reagent combination of FeBr2/Et3N, on the other hand, exhibited a broader catalytic scope, owing to the beneficial effect of Et3N. This latter catalyst system enables 2-azido-2-methyl-1,3-dicarbonyl compounds to be converted to the corresponding enamides under mild conditions in good yields.
- Yang, Tonghao,Lin, Yajun,Yang, Chaoqun,Yu, Wei
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supporting information
p. 6097 - 6102
(2019/11/20)
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- Iron-Catalyzed Acyl Migration of Tertiary α-Azidyl Ketones: Synthetic Approach toward Enamides and Isoquinolones
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This paper reports that tertiary α-azidyl phenyl ketones can be transformed into enamides by treatment with FeBr2 at elevated temperature in DMF. The reaction proceeds via 1,2-benzoyl migration from α-carbon to the nitrogen atom, accompanied by expulsion of a nitrogen molecule. This protocol is suitable for the synthesis of N-(cyclopent-1-en-1-yl)benzamides, N-(cyclohex-1-en-1-yl)benzamides, and N-benzoyl-α-methyl enamines and provides a convenient approach toward isoquinolones.
- Yang, Tonghao,Fan, Xing,Zhao, Xiaopeng,Yu, Wei
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p. 1875 - 1879
(2018/04/16)
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- USE OF DDX3 INHIBITORS AS ANTIPROLIFERATIVE AGENTS
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The present invention refers to compounds of formula I or II endowed with DDX3 inhibitory activity, relative pharmaceutical compositions and their use as antihyperproliferative agents. (I) or (II)
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Page/Page column 83; 84
(2017/10/30)
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- HUMAN HELICASE DDX3 INHIBITORS AS THERAPEUTIC AGENTS
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The present invention refers to compounds endowed with RNA helicase DDX3 inhibitory activity of formula I and II and their therapeutic use, in particular for the treatment of viral diseases.
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Page/Page column 91
(2016/09/22)
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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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- The design, synthesis and structure-activity relationships of 1-aryl-4-aminoalkylisoquinolines: A novel series of CRF-1 receptor antagonists
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The design, synthesis and structure-activity relationships of a novel series of CRF-1 receptor antagonist, the 1-aryl-4-alkylaminoisoquinolines, is described. The effects of substitution on the aromatic ring, the amino group and the isoquinoline core on C
- Yoon, Taeyoung,De Lombaert, Stephane,Brodbeck, Robbin,Gulianello, Michael,Chandrasekhar, Jayaraman,Horvath, Raymond F.,Ge, Ping,Kershaw, Mark T.,Krause, James E.,Kehne, John,Hoffman, Diane,Doller, Dario,Hodgetts, Kevin J.
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p. 891 - 896
(2008/09/18)
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- 1-ARYL-4-SUBSTITUTED ISOQUINOLINES
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1-Aryl-4-substituted isoquinolines analogues of Formula (I) and Formula (II) are provided, as follows : wherein R1, R2, R3, R8, R9, A and Ar are defined herein. Such compounds are ligands of C5a receptors. Preferred compounds of Formula (I) and (II) bind to C5a receptors with high affinity and exhibit neutral antagonist or inverse agonist activity at C5a receptors. The present invention also relates to pharmaceutical compositions compositions comprising such compounds, and to the use of such compounds in treating a variety of inflammatory, cardiovascular, and immune system disorders. In addition, the present invention provides labeled 1-aryl-4-substituted isoquinolines, which are useful as probes for the localization of C5a receptors.
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- Poly(ADP-ribose) polymerase-1 (PARP-1) inhibitors based on a tetrahydro-1(2H)-isoquinolinone Scaffold: Synthesis, biological evaluation and X-ray crystal structure
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The synthesis, activity and physical properties of two series of novel potent tetrahydro-1(2H)-isoquinolinone based PARP-1 inhibitors are described. The new structural classes with a non-planar ring system interact specifically with the PARP-1 protein at the nicotinamide-binding site. Georg Thieme Verlag Stuttgart.
- Peukert, Stefan,Schwahn, Uwe,Guessregen, Stefan,Schreuder, Herman,Hofmeister, Armin
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p. 1550 - 1554
(2007/10/03)
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- SUBSTITUTED PYRIDONES AS INHIBITORS OF POLY(ADP-RIBOSE) POLYMERASE (PARP)
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The present invention discloses and claims a series of 2,3,5-substituted pyridone derivatives as defined herein. This invention also relates to methods of making these compounds. The compounds of this invention are inhibitors of poly(adenosine 5'-diphosphate ribose) polymerase (PARP) and are therefore useful as pharmaceutical agents, especially in the treatment and/or prevention of a variety of diseases, including diseases associated with the central nervous system and cardiovascular disorders.
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Page/Page column 72
(2010/02/14)
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- SUBSTITUTED TETRAHYDRO-2H-ISOQUINOLIN-1-ONE DERIVATIVES, METHOD FOR THE PRODUCTION THEREOF, AND USE OF THE SAME AS MEDICAMENTS
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The invention relates to compounds of general formula (I), the designations of the substituents R1, R2, Ar and X being cited in the description, and to the physiologically compatible salts thereof. The invention also relates to a method for producing said compounds, and to the use thereof as medicaments. The inventive compounds are poly(ADP-ribose)polymerase (PARP) inhibitors.
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Page/Page column 47
(2008/06/13)
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- Synthesis of novel substituted isoquinolones
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A series of novel substituted isoquinolones have been synthesised. This has been achieved by two routes, either Curtius rearrangment of cinnamic acids or via an isoquinoline N-oxide.
- Briet, Nicolas,Brookes, Michael H,Davenport, Richard J,Galvin, Frances C.A,Gilbert, Philip J,Mack, Stephen R,Sabin, Verity
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p. 5761 - 5766
(2007/10/03)
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- On the Chemistry of Pyrrole Pigments, XCI: Copper Complexes of Pyridinologous Linear Tri- and Tetra-pyrroles as Cyclopropanation Catalysts
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In addition to two recently described pyridinologous linear tri- and tetrapyrroles a biisoquinologous system was prepared and its geometrical features derived by means of NMR measurements and force field calculations.The copper complexes of these three ligands were isolated and characterized, and then used as catalysts in the cyclopropanation of styrene.The results were found to be similar to those reported for a variety of catalysts in literature.Thus, it was demonstrated that these systems can be used in principle as catalysts. - Keywords.Pyridinologous linear tri- and tetrapyrroles; Copper chelates; 1H-NMR spectra; Configuration; Conformation; Cyclopropanation catalyst.
- Falk, H.,Suste, A.
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p. 325 - 334
(2007/10/02)
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- Synthesis of some triazolo- and tetrazolo-isoquinolines
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The isocoumarins (Ia-c) on treatment with ammonia-ethanol give isoquinolones (IIa-c) which react with POCl3-PCl5 affording 1-chloroisoquinolines (IIIa-c).Further reaction with hydrazine furnishes 1-hydrazinoisoquinolines (
- Bhide, B H,Akolkar, V D,Brahmbhatt, D I
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p. 675 - 678
(2007/10/02)
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- The Chemistry of Phthalide-3-carboxylic Acid. VII Reaction with Isoquinoline Derivatives
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Phthalide-3-carboxylic acid has been decarboxylated in the presence of isoquinoline, 1-chloroisoqinoline and isoquinoline N-oxides to give low yields of compounds resulting from alkylation of the isoquinoline heterocycle at C1 with a phthalidyl group.Attempted Barton decarboxylation-alkylation in the presence of isoquinolinium salts was unsuccessful.
- Donati, Cosimo,Hung, Tran V.,Prager, Rolf H.
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p. 375 - 381
(2007/10/02)
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- HETEROCYCLIC SYNTHESIS VIA THALLATION AND SUBSEQUENT PALLADIUM-PROMOTED OLEFINATION
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The thallation and subsequent palladium-promoted olefination of p-tolylacetic acid, N-methylbenzamide, benzamide and acetanilide provides a novel new route to a variety of important oxygen and nitrogen heterocycles.
- Larock, R.C.,Liu, C.-L.,Lau, H. H.,Varaprath, S.
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p. 4459 - 4462
(2007/10/02)
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- RADICAL ION PAIR MECHANISM OF PHOTOCHEMICAL ISOMERIZATION OF ISOQUINOLINE N-OXIDE IN HYDROXYLIC SOLVENTS, INCLUDING THE MAGNETIC FIELD EFFECT
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It was found that, while the photochemical isomerization of isoquinoline N-oxide into lactam shows magnetic field effect due to HFI-J mechanism, the N-oxides bearing an electron-donating substituent are insensitive to an external magnetic field.The results support strongly "radical ion pair mechanism" of the photochemical isomerization.
- Hata, Norisuke,Yagi, Atsushi
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p. 309 - 312
(2007/10/02)
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- A New Synthesis of Benzopyranopyrazole and Synthesis of N-Amino-1(2H)-isoquinolones
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Interaction of hydrazine with 4-acylisochroman-1,3-dione furnishes benzopyranopyrazole (V) and N-amino-1(2H)-3-alkyl-isoquinolone (VI) in nearly equal amounts.N-Amino-3-alkylisoquinolone is the sole product of interaction of hydrazine with 3-alkylisocoumarin, 4-carboxy-3-alkylisocoumarin and with 2-carboxybenzylalkyl ketone.A number of benzopyrazoles and N-aminoisoquinolones have been synthesised and their structures established.
- Datta, Debashish,Usgaonkar, R. N.
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p. 376 - 379
(2007/10/02)
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- Isoquinolones: Part IV - Synthesis of 3-Methylisoquinolone-4-carboxylic Acids and Action of Ammonia and Aqueous Methyl Amine on 3-Methylisocoumarin-4-carboxylic Acid Esters
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Ammonia reacts with 3-methylisocoumarin-4-carboxylic acid ester (II) on a boiling water-bath to give homophthalimide (III, R'=H) and 3-methylisoquinolone-4-carboxylic acid ester (IV) in nearly equal amounts.At room temperature ammonia reacts to give IV as the major product in good yield.Aq. methyl amine, however, reacts with II to give N-methylhomophthalimide (III, R'=Me) as the major product along with small amounts of compound VI (R1=Me) and some unchanged isocoumarin.Formation of the various products has been rationalised.
- Datta, D.,Tirodkar, R. B.,Usgaonkar, R. N.
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p. 641 - 643
(2007/10/02)
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