- One-pot synthesis of 3-substituted isoquinolin-1-(2H)-ones and fused isoquinolin-1-(2H)-ones by SRN1 reactions in DMSO
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3-Substituted isoquinolin-1-(2H)-ones and fused isoquinolin-1-(2H)-ones have been obtained by the photostimulated SRN1 reactions of 2-iodobenzamide with the enolates of aromatic (acetophenone, 1-(benzo[d][1,3]dioxol-5-yl)ethanone, 1- and 2-naph
- Guastavino, Javier F.,Barolo, Silvia M.,Rossi, Roberto A.
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Read Online
- Reaction Outcome Critically Dependent on the Method of Workup: An Example from the Synthesis of 1-Isoquinolones
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A striking dependence on the method of workup has been found for annulation of benzonitriles ArCN to N-methyl 2-toluamide (1), facilitated by n-BuLi (2 equiv): Quenching the reaction by a slow addition of water produced the expected 1-isoquinolones 2; by
- Matou?, Petr,Májek, Michal,Kysilka, Ond?ej,Kune?, Ji?í,Ma?íková, Jana,R??i?ka, Ale?,Pour, Milan,Ko?ovsky, Pavel
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p. 8078 - 8088
(2021/06/21)
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- C2-substituted quinazolinone derivatives exhibit A1 and/or A2A adenosine receptor affinities in the low micromolar range
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Antagonists of the adenosine receptors (A1 and A2A subtypes) are widely researched as potential drug candidates for their role in Parkinson's disease-related cognitive deficits (A1 subtype), motor dysfunction (A2A subtype) and to exhibit neuroprotective properties (A2A subtype). Previously the benzo-α-pyrone based derivative, 3-phenyl-1H-2-benzopyran-1-one, was found to display both A1 and A2A adenosine receptor affinity in the low micromolar range. Prompted by this, the α-pyrone core was structurally modified to explore related benzoxazinone and quinazolinone homologues previously unknown as adenosine receptor antagonists. Overall, the C2-substituted quinazolinone analogues displayed superior A1 and A2A adenosine receptor affinity over their C2-substituted benzoxazinone homologues. The benzoxazinones were devoid of A2A adenosine receptor binding, with only two compounds displaying A1 adenosine receptor affinity. In turn, the quinazolinones displayed varying degrees of affinity (low micromolar range) towards the A1 and A2A adenosine receptor subtypes. The highest A1 adenosine receptor affinity and selectivity were favoured by methyl para-substitution of phenyl ring B (A1Ki = 2.50 μM). On the other hand, 3,4-dimethoxy substitution of phenyl ring B afforded the best A2A adenosine receptor binding (A2AKi = 2.81 μM) among the quinazolinones investigated. In conclusion, the quinazolinones are ideal lead compounds for further structural optimization to gain improved adenosine receptor affinity, which may find therapeutic relevance in Parkinson's disease-associated cognitive deficits and motor dysfunctions as well as exerting neuroprotective properties.
- Pieterse, Lianie,Terre'Blanche, Gisella,van der Walt, Mietha M.
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supporting information
(2020/06/08)
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- Triflic acid mediated sequential cyclization of ortho-alkynylarylesters with ammonium acetate
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A triflic acid (TfOH) mediated sequential cyclization of ortho-alkynylarylesters and ammonium acetate (NH4OAc) was reported. The reaction took place via a Br?nsted acid-mediated intramolecular cyclization of ortho-alkynylarylesters followed by an ammonium acetate participated substitution reaction, forming isoquinolin-1-ones as the major products. Different from most of the known synthetic methods of isoquinolin-1-ones, no metal catalyst was required in the reported reaction. The regioisomers – isoindolin-1-ones were obtained together with isoquinolin-1-ones in a few cases. The intermediate compounds – isochromen-1-ones and isobenzofuran-1-ones were also isolated. The interconversion experiments showed that the regioisomers formed during the Br?nsted acid induced intramolecular cyclization of ortho-alkynylarylesters. A natural product – ruprechstyril was prepared in a moderate yield employing the new method.
- Domaradzki, Maciej E.,Liu, Xiaochen,Ong, Jiye,Yu, Gyeongah,Zhang, Gan,Simantov, Ariel,Perl, Eliyahu,Chen, Yu
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- Synthesis and Application of Heterocyclic Germatranes via Rhodium-Catalyzed Directed C?H Activation/Annulation with Alkynyl Germatranes and Palladium-Catalyzed Cross-Coupling
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Rhodium-catalyzed C?H activation and annulation with alkynyl germatranes for the synthesis of heterocyclic germatranes is described. Various heterocyclic germatranes were constructed by this protocol and applied in multiple derivatizations such as palladi
- Xu, Meng-Yu,Wang, Chao,Jiang, Wei-Tao,Xiao, Bin
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p. 1706 - 1711
(2020/03/19)
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- Nickel-Catalyzed Tandem Reaction of Functionalized Arylacetonitriles with Arylboronic Acids in 2-MeTHF: Eco-Friendly Synthesis of Aminoisoquinolines and Isoquinolones
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The first example of the nickel-catalyzed tandem addition/cyclization of 2-(cyanomethyl)benzonitriles with arylboronic acids in 2-MeTHF has been developed, which provides the facile synthesis of aminoisoquinolines with good functional group tolerance under mild conditions. This chemistry has also been successfully applied to the synthesis of isoquinolones by the tandem reaction of methyl 2-(cyanomethyl)benzoates with arylboronic acids. The use of the bio-based and green solvent 2-MeTHF as the reaction medium makes the synthesis process environmentally benign. The synthetic utility of this chemistry is also indicated by the synthesis of biologically active molecules.
- Zhen, Qianqian,Chen, Lepeng,Qi, Linjun,Hu, Kun,Shao, Yinlin,Li, Renhao,Chen, Jiuxi
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supporting information
p. 106 - 111
(2019/12/11)
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- Ruthenium(II)-Catalyzed Homocoupling of Weakly Coordinating Sulfoxonium Ylides via C?H Activation/Annulations: Synthesis of Functionalized Isocoumarins
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Homocoupling of weakly coordinating sulfoxonium ylides was accomplished via ruthenium (II) catalyzed C?H activation process. This strategy provides a convenient, efficient and step-economic method to access 3-substituted isocoumarins with good functional
- Zhou, Ming-Dong,Peng, Zhen,Wang, He,Wang, Zhao-Hui,Hao, Da-Jin,Li, Lei
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supporting information
p. 5191 - 5197
(2019/11/13)
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- Tunable Synthesis of 3-Hydroxylisoquinolin-1,4-dione and Isoquinolin-1-one Enabled by Copper-Catalyzed Radical 6- endo Aza-cyclization of 2-Alkynylbenzamide
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In this work, switchable synthesis of isoquinolin-1-one and 3-hydroxylisoquinolin-1,4-dione from 2-alkynylbenzamide is reported. The transformation works well with good yields and a broad reaction scope. The synthetic switch for providing isoquinolin-1-one and 3-hydroxylisoquinolin-1,4-dione is enabled by the use of a N2 or O2 atmosphere. Mechanism studies show that the reaction proceeds in a regioselective manner via a N-center radical 6-endo-dig aza-cyclization pathway.
- Liu, Renzhi,Li, Meng,Xie, Wenlin,Zhou, Hongwei,Zhang, Yajing,Qiu, Guanyinsheng
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p. 11763 - 11773
(2019/10/02)
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- Palladium-Catalyzed Inert C?H Bond Activation and Cyclocarbonylation of Isoquinolones with Carbon Dioxide Leading to Isoindolo[2,1-b]isoquinoline-5,7-Diones
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A palladium-catalyzed inert C?H bond activation and cyclocarbonylation of isoquinolones leading to isoindolo[2,1-b]isoquinoline-5,7-diones under 1 atm of carbon dioxide has been developed. This transformation features high regio- and chemo-selectivity, step-economy, and good functional group tolerance. Most of the corresponding products were obtained in moderate to good yields. It offers an alternative approach for the synthesis of useful diverse isoindolo[2,1-b]isoquinoline-5,7-dione derivatives. (Figure presented.).
- Yan, Kelu,Jin, Junbin,Kong, Yong,Li, Bin,Wang, Baiquan
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supporting information
p. 3080 - 3085
(2019/05/21)
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- Electroremovable Traceless Hydrazides for Cobalt-Catalyzed Electro-Oxidative C-H/N-H Activation with Internal Alkynes
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Electrochemical oxidative C-H/N-H activations have been accomplished with a versatile cobalt catalyst in terms of [4 + 2] annulations of internal alkynes. The electro-oxidative C-H activation manifold proved viable with an undivided cell setup under exceedingly mild reaction conditions at room temperature using earth-abundant cobalt catalysts. The electrochemical cobalt catalysis prevents the use of transition metal oxidants in C-H activation catalysis, generating H2 as the sole byproduct. Detailed mechanistic studies provided strong support for a facile C-H cobaltation by an initially formed cobalt(III) catalyst. The subsequent alkyne migratory insertion was interrogated by mass spectrometry and DFT calculations, providing strong support for a facile C-H activation and the formation of a key seven-membered cobalta(III) cycle in a regioselective fashion. Key to success for the unprecedented use of internal alkynes in electrochemical C-H/N-H activations was represented by the use of N-2-pyridylhydrazides, for which we developed a traceless electrocleavage strategy by electroreductive samarium catalysis at room temperature.
- Mei, Ruhuai,Sauermann, Nicolas,Oliveira, Jo?o C. A.,Ackermann, Lutz
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p. 7913 - 7921
(2018/06/08)
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- Rhodium(III)-catalyzed chemodivergent annulations between: N-methoxybenzamides and sulfoxonium ylides via C-H activation
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Chemodivergent and redox-neutral annulations between N-methoxybenzamides and sulfoxonium ylides have been realized via Rh(iii)-catalyzed C-H activation. The sulfoxonium ylide acts as a carbene precursor, and coupling occurs under acid-controlled condition
- Xu, Youwei,Zheng, Guangfan,Yang, Xifa,Li, Xingwei
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p. 670 - 673
(2018/01/28)
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- Direct access to cobaltacycles via C-H activation: N-chloroamide- enabled room-temperature synthesis of heterocycles
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Cobaltacycle synthesis via C-H activation has been achieved for the first time, providing key mechanistic insight into cobalt catalytic chemistry. NChloroamides are used as a directing synthon for cobalt-catalyzed roomtemperature C-H activation and construction of heterocycles. Alkynes as coupling partners allow convenient access to isoquinolones, a class of synthetically and pharmaceutically important compounds. The broad substrate scope enables a diverse range of substitution patterns to be incorporated into the heterocyclic scaffold.
- Yu, Xiaolong,Chen, Kehao,Guo, Shan,Shi, Pengfei,Song, Chao,Zhu, Jin
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p. 5348 - 5351
(2017/11/07)
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- On-Water Silver(I)-Catalyzed Cycloisomerization of Acetylenic Free Amines/Amides towards 7-Azaindole/Indole/Isoquinolone Derivatives
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Silver-catalyzed on-water intramolecular cyclization of acetylenic free amines is reported, which affords 7-azaindoles in good to excellent yields. Neither strong base/acid catalysts nor N-substituted substrates are required to achieve this cycloisomerization. Hydrogen bonds between water medium and the substrates play an important role in improving chemical reactivity and regioselectivity. Furthermore, the on-water reaction is extendable to acetylenic amides for isoquinolone synthesis.
- Sun, Hongpeng,Xiao, Li,Li, Wei,Xie, Qiong,Shao, Liming
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supporting information
p. 4845 - 4852
(2017/10/06)
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- Synthetic method of topoisomerase I inhibitor
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The invention relates to a synthetic method of a topoisomerase I inhibitor, which is piperazine (4-methyl piperazine-1-radical)-3-phenylisoquinoline as shown in the following formula (V). A total synthetic route of the synthetic method is as shown in the
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Paragraph 0050-0053
(2017/07/08)
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- Method for synthesizing anti-cancer inhibitor intermediate
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The invention relates to a method for synthesizing an isoquinolone derivative of formula (III) as an anti-cancer inhibitor intermediate. The method comprises the step: in a reaction solvent, in the presence of a catalyst, a nitrogen-containing ligand, an acid additive and 4-dimehtyl aminopyridine, performing a reaction on a compound of formula (I) as shown in the specification and a compound of formula (II) as shown in the specification, and after posttreatment, obtaining a compound of formula (III) as shown in the specification, wherein in the formulae, R1 is C1-C6 alkyl; R2 is H, halogen, C1-C6 alkyl or C1-C6 alkoxy; or R2 and substituted phenyl form naphthyl; and M is an alkali metal element. By adopting the method, due to comprehensive selection and mutual action of a reaction substrate, the catalyst, the nitrogen-containing ligand, the acid additive, the 4-dimehtyl aminopyridine and the solvent, the substrate range can be widened, a target product of high yield can be obtained, an intermediate of relatively rich diversities can be provided for synthesis of the compounds and development and synthesis of anti-cancer inhibitor medicines, and good research values and application potential can be achieved.
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Paragraph 0040-0043
(2017/07/12)
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- Tandem addition/cyclization for access to isoquinolines and isoquinolones via catalytic carbopalladation of nitriles
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The first example of the palladium-catalyzed sequential nucleophilic addition followed by an intramolecular cyclization of functionalized nitriles with arylboronic acids has been achieved, providing an efficient synthetic pathway to access structurally di
- Qi, Linjun,Hu, Kun,Yu, Shuling,Zhu, Jianghe,Cheng, Tianxing,Wang, Xiaodong,Chen, Jiuxi,Wu, Huayue
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supporting information
p. 218 - 221
(2017/11/27)
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- Synthetic method of antitumor nitrogen-containing heterocyclic drug intermediates
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The invention relates to a synthetic method of isoquinolinone compounds shown by formula (III) shown in the description and acting as antitumor nitrogen-containing heterocyclic drug intermediates; the method comprises: enabling a compound of formula (I) shown in the description and a compound of formula (II) shown in the description to react in a reaction solvent in the presence of a catalyst, a nitrogen-containing ligand and an acid catalyst, and treating after reaction to obtain the compound of formula (III), wherein R1 is C1-C6 alkyl, and R2 is H, halogen, C1-C6 alkyl or C1-C6 alkoxy, or R2 and R2-substituted phenyl form naphthyl. Through the comprehensive selection and interaction of a reaction substrate, catalysts, nitrogen-containing ligands, acid catalysts, reaction solvents and the like according to the method, the substrate range is widened, and the isoquinolinone compound is acquired at high yield; more diversified intermediates are provided for novel synthesis of the compounds and the research, development and synthesis of antitumor drugs, and the compounds have good research value and application potential.
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Paragraph 0038-0043
(2017/07/06)
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- Synthesis method of anti-tumor medicine compound
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The invention relates to a synthesis method of an anti-tumor medicine compound, namely a compound shown as the formula (V). A total synthesis route of the synthesis method is shown as the description. According to the method provided by the invention, a s
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Paragraph 0069 - 0072
(2017/08/26)
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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; 0055-0076; 0081-0084; 0089-0090
(2017/05/19)
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- A different quinolinone and its derivatives
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The invention belongs to the technical field of pharmaceutical and chemical intermediates and related chemicals and relates to a preparation method of isoquinolone and derivatives thereof. The isoquinolone and derivatives thereof are important biologically active molecules, skeletal structures frequently appear in natural molecules and drug molecules, and have better therapeutic effect on hypertension, cancer and anxiety disorders and important applications in the fields of organic synthesis and pharmaceutical chemistry. The method is short in synthesis route, mild in conditions and simple in operation and is expected to achieve industrial production and has the advantages of short synthetic route, mild conditions, simple operation and high yield and the like. The isoquinolone and derivatives thereof have greater application value and social and economic benefits.
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Paragraph 0031-0033
(2017/05/02)
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- Isoquinolone synthesis through SNAr reaction of 2-halobenzonitriles with ketones followed by cyclization
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An efficient method for the synthesis of isoquinolones through base KOtBu-promoted SNAr reaction of 2-halobenzonitriles with ketones followed by Lewis acid Cu(OAc)2-catalyzed cyclization is described. Isoquinolone derivati
- Mayo, Muhammad Shareef,Yu, Xiaoqiang,Feng, Xiujuan,Yamamoto, Yoshinori,Bao, Ming
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p. 3998 - 4002
(2015/05/05)
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- Copper-catalyzed selective synthesis of isoindolin-1-ones and isoquinolin-1-ones from the three-component coupling of 2-halobenzoic acid, alkynylcarboxylic acid and ammonium acetate
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Isoindolin-1-ones and isoquinolin-1-ones were selectively synthesized from the reaction of 2-halobenzoic acid, arylalkynylcarboxylic acid and ammonium acetate (NH4OAc) in the presence of cesium carbonate (Cs2CO3) and a copper catalyst. Conducting the reaction under one-pot conditions provided isoindolin-1-ones in good yields. Changing the addition sequence of ammonium acetate after all reagents had reacted at 120 °C for 6 h selectively produced isoquinolin-1-ones. A variety of arylalkynylcarboxylic acids produced the corresponding isoindolin-1-ones and isoquinolin-1-ones in good yields.
- Irudayanathan, Francis Mariaraj,Noh, Jieun,Choi, Jinseop,Lee, Sunwoo
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p. 3433 - 3442
(2015/01/09)
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- α-MsO/TsO/Cl ketones as oxidized alkyne equivalents: Redox-neutral rhodium(III)-catalyzed C-H activation for the synthesis of N-heterocycles
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α-Halo and pseudohalo ketones are used for the first time as C(sp3)-based electrophiles in transition-metal-catalyzed C-H activation and as oxidized alkyne equivalents in RhIII-catalyzed redox-neutral annulations to generate diverse N-heterocycles. This transformation is efficient and scalable. Due to the mild reaction conditions, a variety of functional groups could be tolerated. Who needs alkynes? α-Halo and pseudohalo ketones (as C(sp3)-based electrophiles) are utilized as oxidized alkyne equivalents in RhIII-catalyzed redox-neutral annulations to efficiently generate diverse N-heterocycles. Owing to the mild reaction conditions, a variety of functional groups are tolerated.
- Yu, Da-Gang,De Azambuja, Francisco,Glorius, Frank
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p. 2754 - 2758
(2014/03/21)
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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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- Tandem reactions leading to benzo[c]chromen-6-ones and 3-substituted isocoumarins
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A simple and convenient protocol for the synthesis of benzo[c]chromen-6- ones and 3-substituted isocoumarins through a CuI-catalyzed tandem reaction of 2-bromobenzoates withcyclohexane-1,3-diones or acyclic 1,3-diones is developed. This strategy can also be extended to the one-pot synthesis of isoquinolin-1(2H)-one and 3,4-dihydrophenanthridine-1,6(2H,5H)-dione. A simple and convenient protocol for the synthesis of benzo[c]chromen-6-ones and 3-substituted isocoumarins through a CuI-catalyzed tandem reaction of 2-bromobenzoates with cyclohexane-1,3-dione or acyclic 1,3-dione has been developed. This strategy can also be extended to the one-pot synthesis of isoquionlin-1(2H)-one and 3,4-dihydrophenanthridine-1,6-(2H,5H)-dione. Copyright
- Fan, Xuesen,He, Yan,Cui, Liangyan,Guo, Shenghai,Wang, Jianji,Zhang, Xinying
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supporting information; experimental part
p. 673 - 677
(2012/03/10)
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- Mild Rh(III)-catalyzed C-H activation and annulation with alkyne MIDA boronates: Short, efficient synthesis of heterocyclic boronic acid derivatives
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Taking advantage of Rh(III)-catalyzed C-H activation reactions, we have developed a mild, short, and efficient method for the synthesis of bench-stable 3-isoquinolone MIDA boronates. The reaction is practical and scalable. The product formed has been applied in the Suzuki-Miyaura reaction with high efficiency. This strategy has also been successfully expanded to the synthesis of MIDA boronate functionalized heterocycles such as isoquinoline, pyrrole, and indole.
- Wang, Honggen,Grohmann, Christoph,Nimphius, Corinna,Glorius, Frank
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supporting information
p. 19592 - 19595
(2013/02/21)
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- A new access to 3-substituted-1(2H)-isoquinolone by tandem palladium-catalyzed intramolecular aminocarbonylation annulation
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An original tribromide derivative based, palladium-catalyzed synthesis of 3-substituted-1(2H)-isoquinolone is described based on a regioselective Suzuki-Miyaura C-C coupling on o-halo-(2,2-dihalovinyl)-benzene followed by a palladium catalyzed amination-carbonylation-cyclization reaction. This sequence efficiently proceeds to build up isoquinolone in fair to good yields over a one-pot 3-bond synthesis reaction. The Royal Society of Chemistry 2012.
- Dieudonne-Vatran, Antoine,Azoulay, Michel,Florent, Jean-Claude
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p. 2683 - 2691
(2012/04/23)
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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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- Ligand-free, PdCl2(PPh3)2 catalyzed, microwaveassisted Suzuki coupling of 1-chloro-3-phenylisoquinoline in the synthesis of diversified 1,3-disubstituted isoquinolines
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An efficient ligand-free, microwave-assisted, Pd-catalyzed, Suzuki coupling of 1-chloro-3-phenylisoquinoline and boronic acids, in the presence of sodium carbonate base and 1,4-dioxane solvent, is reported for the synthesis of diversified 1,3-disubstitute
- Prabakaran,Khan, F. Nawaz,Jin, Jong Sung
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scheme or table
p. 337 - 346
(2012/05/20)
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- Synthesis of diversified thioethers, 1-aroylalkylisoquinolin-1-yl thioethers, by electrophilic S-alkylation of 3-phenyl isoquinoline-1(2H)-thione
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A mild and efficient method for the synthesis of thioethers has been developed. The 3-phenylisoquinoline-1(2H)-thione underwent S-alkylation to afford structurally diverse sulfides in high yield. Copyright
- Manivel,Khan, F. Nawaz,Hatwar, Venkatesha R.
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experimental part
p. 1932 - 1942
(2010/11/18)
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- Platinum(II)-catalyzed intramolecular cyclization of alkynylbenzonitriles: Synthesis of 1-alkoxyisoquinolines and isoquinolones
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A facile synthesis of a series of 1-alkoxyisoquinolines and (2H)-isoquinolones by an intramolecular 6-endo-dig cyclization of ortho-alkynylbenzonitriles in the presence of a catalytic amount of hydrido(dimethylphosphinous acid-κP)[hydrogen bis(dimethylphosphinito- κP)]platinum(II) in various alcohols at 65-90 °C is described for the first time.
- Li, Jim,Chen, Lijing,Chin, Elbert,Lui, Alfred S.,Zecic, Hasim
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experimental part
p. 6422 - 6425
(2010/12/25)
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- Synthesis of highly substituted isoquinolone derivatives by nickel-catalyzed annulation of 2-halobenzamides with alkynes
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(Equation Presented). An efficient method for the synthesis of substituted 1(2H)-isoquinolone derivatives via nickel-catalyzed annulation of substituted 2-halobenzamides with alkynes is described. This protocol is successfully applied to the total synthes
- Liu, Chuan-Che,Parthasarathy, Kanniyappan,Cheng, Chien-Hong
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supporting information; experimental part
p. 3518 - 3521
(2010/10/02)
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- Synthesis of some new 2,4-disubstituted hydrazinothiazoles and 2,5-disubstituted thiazolidinones
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A series of hydrazinothiazoles has been synthesized by the condensation of thiosemicarbazones and α-bromoketones. Similarly the hydrazinothiazolidiones were prepared by the condensation of thiosemicarbazone and α-bromoesters. The newly synthesized compounds were characterized by NMR and LCMS studies.
- Manivel,Khan, F. Nawaz
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experimental part
p. 2910 - 2922
(2010/04/05)
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- A dramatic substituent effect in silver(I)-catalyzed regioselective cyclization of ortho-alkynylaryl aldehyde oxime derivatives
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A dramatic substituent effect was found in the silver(I)-catalyzed cyclization reaction of ortho-alkynylaryl aldehyde oxime derivatives. When R is an alkyl group, the Ag(I)-catalyzed reaction in dimethylacetamide at 110°C (conditions A) affords isoquinoli
- Gao, Hongyin,Zhang, Junliang
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supporting information; experimental part
p. 85 - 88
(2009/10/02)
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- New pyridine N-oxides as chiral organocatalysts in the asymmetric allylation of aromatic aldehydes
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Asymmetric allylation of aromatic aldehydes 1 with allyltrichlorosilane (2) can be catalyzed by new terpene-derived bipyridine N,N′-dioxides 12-15 and an axially chiral biisoquinoline dioxide 17b with good enantioselectivities. Dioxides have been found to be more reactive catalysts than their monooxide counterparts. Crown Copyright
- Malkov, Andrei V.,Westwater, Mary-Margaret,Gutnov, Andrey,Ramírez-López, Pedro,Friscourt, Frédéric,Kadl?íková, Aneta,Hoda?ová, Jana,Rankovic, Zoran,Kotora, Martin,Ko?ovsky, Pavel
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experimental part
p. 11335 - 11348
(2009/04/11)
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- A tandem elimination-cyclization-suzuki approach: Efficient one-pot synthesis of functionalized (Z)-3-(arylmethylene)isoindolin-1-ones
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(Chemical Equation Presented) A novel and efficient one-pot regioselective elimination-cyclization-Suzuki approach was developed to afford (Z)-3-arylmethyleneisoindolin-1-ones in good to excellent yields from easily accessible o-gem-dihalovinylbenzamides and organoboron reagents.
- Sun, Caiyun,Xu, Bin
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supporting information; experimental part
p. 7361 - 7364
(2009/05/07)
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- Tandem C-C coupling - Intramolecular acetylenic Schmidt reaction under Pd/C-Cu catalysis
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A new one-pot reaction for the regioselective construction of a six-membered fused N-heterocyclic ring leading to isoquinolones under Pd/C-Cu catalysis is described. The Royal Society of Chemistry.
- Batchu, Venkateswara Rao,Barange, Deepak Kumar,Kumar, Dinesh,Sreekanth, Bukkapattanam R.,Vyas,Reddy, E. Amarender,Pal, Manojit
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p. 1966 - 1968
(2008/02/08)
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- Synthesis of new 3-arylisoquinolinamines: Effect on topoisomerase I inhibition and cytotoxicity
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To investigate the structure-activity relationships of 3-arylisoquinolines, diverse substituted 3-aryisoquinolinamines were synthesized and tested in vitro antitumor activity against four tumor cell lines. Some of the compounds showed potent topoisomerase I inhibitory activity. Docking study of 7d with topoisomerase I-DNA complex was also performed.
- Cho, Won-Jea,Min, Sun Young,Le, Thanh Nguyen,Kim, Tae Sung
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p. 4451 - 4454
(2007/10/03)
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- Reaction of 3-substituted and 4-bromo-3-substituted isoquinolin-1-(2H)-ones with propargyl bromide
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Isoquinolinones were brominated using N-bromosuccinimide in dimethylformamide at room temperature to give 4-bromo-3-substituted isoquinolin-1-(2H)-ones. The reaction of these isoquinolinones with propargyl bromide in the presence of anhydrous potassium carbonate yielded N and O-alkylated products.
- Usifoh
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p. 597 - 600
(2007/10/03)
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- Solvent effects on aza-anionic cycloaromatization of 2-(2-substituted-ethynyl)benzonitriles
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The methanolysis of 2-(2-aryl ethynyl)benzonitriles is accelerated when the polar aprotic solvents are added, which could enhance the 6-endo pathway and give isoquinolones, though the 5-exo pathway is occupied mostly. The yields of products would also be
- Lin, Chi-Fong,Yang, Jia-Huei,Hsieh, Pei-Chen,Lu, Wen-Der,Wu, Ming-Jung
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p. 211 - 214
(2007/10/03)
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- Asymmetric synthesis of 4-hydroxy-3-phenyltetrahydroisoquinoline derivatives using enantiopure sulfinimines (N-sulfinyl imines)
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Addition of lateral lithiated amides and phthalide anions to enantiopure sulfinimines (N-sulfinyl imines) represents a new approach for the asymmetric synthesis of 3-substituted isoquinolones and 3-substituted 4-hydroxy isoquinolones, respectively, important chiral building blocks for isoquinoline alkaloid synthesis. In one example 3-phenylisoquinolone (-)-15b was prepared in >95% ee by treatment of amide ion 10b with sulfinimine (S)- (+)-11 and subsequent deprotection of the N-sulfinyl auxiliary and cyclization. Oxaziridine-mediated hydroxylation of the anion of 16 afforded 4-hydroxy isoquinolone 19, which was transformed into 4-hydroxy-3- phenyltetrahydroisoquinoline (-)-22. In another approach 22 was prepared more directly by addition of phthalide ion 26 to (S)-(+)-11, creating the two stereogenic centers simultaneously. The selectivity proved to be highly counterion dependent.
- Davis, Franklin A.,Andemichael, Yemane W.
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p. 8627 - 8634
(2007/10/03)
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- Synthesis and biological evaluation of 3-arylisoquinolines as antitumor agents
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To investigate the structure-activity relationship of 7,8-dimethoxy-2-methyl-3-(4,5-methylenedioxy-2-vinylphenyl)isoquinolin-1(2H) -one 2, diverse substituted 3-arylisoquinolines were synthesized and tested in vitro antitumor activity against five human tumor cell lines. The results showed a broad antitumor spectrum for a series of 3-arylisoquinolines.
- Cho, Won-Jea,Park, Myun-Ji,Chung, Byung-Ho,Lee, Chong-Ok
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- A convenient way to dibenzo[c,h]-1,5-naphthyridines (11-aza-benzo[c] phenanthridines)
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Whereas thermal cyclisation of variously substituted 2,3-diarylacrylazides easily provided a new way to 3-aryl-isoquinolones, nitration of these compounds mainly led to corresponding 3-aryl-4-nitro-isoquinolones. After reduction into 4-amino-3-aryl-isoquinolones, amidification and subsequent cyclization gave the yet unknown title compounds.
- Bisagni, Emile,Landras, Corinne,Thirot, Sylvie,Huel, Christiane
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p. 10427 - 10440
(2007/10/03)
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- Biphenylmethyl-substituted pyridones
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Biphenylmethyl-substituted pyridones are prepared by reaction of pyridones with appropriate biphenylmethyl compounds. The biphenylmethyl-substituted pyridones can be employed as active compounds in medicaments, in particular for the treatment of arter
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- Synthesis of Isocoumarin, 1-Isoquinolone and 4(1H)-Quinolone Derivatives via Seleno-intermediates
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The reaction of 2-styrylbenzoic acid 2 with N-phenylselenosuccinimide (N-PPS) affords 3-phenyl-iso-coumarin derivatives 3 and 3,4-dihydro-3-phenyl-4-(phenylseleno)isocoumarins 4 via selenolactonization.The reaction of 2-styrylbenzamides 5 and 1-(2-aminoph
- Izumi, Taeko,Morishita, Nobuya
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p. 145 - 152
(2007/10/02)
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- Sulfonylbenzyl-substituted benzo- and pyridopyridones
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Sulfonylbenzyl-substituted benzo- and pyridopyridones are prepared by reacting corresponding benzo- and pyridopyridones with sulphonylbenzyl compounds. The sulphonylbenzyl-substituted benzo- and pyridopyridones can be employed as active compounds in medicaments, in particular for the treatment of arterial hyper tension and atherosclerosis.
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- Organopalladium mediated synthesis of isocarbostyrils
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3-Substituted-isocarbostyrils have been synthesised by the cyclisation of 2-alkynylbenzamides with palladium reagents.
- Nagarajan, A.,Balasubramanian, Tiruvenkat R.
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- Hydrosulfite Reduction of N-Nitroso-1,2,3,4-tetrahydroisoquinolines and Oxidation of N-Amino-1,2,3,4-tetrahydroisoquinolines
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The sodium hydrosulfite reduction of N-nitroso-1,2,3,4,-tetrahydroisoquinolines (5) does not result in the loss of nitrogen and leads to the corresponding hydrazine 6 which upon oxidation with mercuric oxide in ethanol at 62 deg gives the hexahydrotetrazine 7 in 39percent yield.Treatment of the n-tosyl derivative of 6 with base affords 7 in nearly quantitative yield.Oxidation of 6 in 1-butanol at 95 deg results in the formation of a complex product mixture from which only one component, 1,1'-azobis-3,4-dihydroisoquinoline (8) could be isolated.Surprisingly the sodium hydrosulfite reduction of 2-nitroso-3-phenyl-1,2,3,4-tetrahydroisoquinoline (15) also failed to proceed with loss of nitrogen and yields the corresponding hydrazine 16.However, 16 was cleanly oxidized by mercuric oxide in ethanol at 62 deg with concurrent elimination of nitrogen to afford 2-phenylindane in 75percent yield.Possible rationalizations for these results are presented.
- Powell, Burwell F.,Overberger, C. G.,Anselme, J.-P.
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p. 121 - 128
(2007/10/02)
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