- Cobalt-Mediated Decarboxylative/Desilylative C?H Activation/Annulation Reaction: An Efficient Approach to Natural Alkaloids and New Structural Analogues
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A Co(II)-mediated decarboxylative/desilylative C?H activation/annulation reaction for the efficient synthesis of 3-arylisoquinolines has been developed. Using alkynyl carboxylic acid and alkynyl silane as terminal alkyne precursors, providing straightforw
- Hai, Li,Lai, Ruizhi,Lv, Shan,Nie, Ruifang,Wu, Yong,Yang, Zhongzhen,chen, Kang
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- Silver/Rhodium Relay Catalysis Enables C?H Functionalization of In Situ Generated Isoquinolines with Sulfoxonium Ylides: Construction of Hexahydrodibenzo[a,g]quinolizine Scaffolds
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Employing silver/rhodium relay catalysis strategy, an intramolecular electrophilic cyclization and C?H activation followed by cascade hydrogenation and reductive amination has been developed. The acylmethylated isoquinoline derivatives could be afforded with broad substrate scope in 23–88% yields, which could be further transformed to the core skeleton of hexahydrodibenzo[a,g]quinolizine as drug-candidates. Moreover, this reaction was achieved in a gram-scale. A reasonable reaction mechanism has been proposed based on a series of control and KIE experiments. (Figure presented.).
- Li, Quanzhe,Liu, Ruixing,Wei, Yin,Shi, Min
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supporting information
p. 2664 - 2669
(2021/04/05)
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- NHC-Mediated Stetter-Aldol and Imino-Stetter-Aldol Domino Cyclization to Naphthalen-1(2 H)-ones and Isoquinolines
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N-Heterocyclic carbene-catalyzed tandem Stetter-aldol reaction of phthalaldehyde and α,β-unsaturated ketimines has been developed to afford functionalized naphthalen-1(2H)-one derivatives as the formal [4+2] annulation product. Interestingly, the reaction of aldimines led to the formation of isoquinoline derivatives instead of the expected indanone derivatives as a [4+1] annulation product.
- Barman, Debabrata,Ghosh, Tanmoy,Show, Krishanu,Debnath, Sudipto,Ghosh, Tapas,Maiti, Dilip K.
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supporting information
p. 2178 - 2182
(2021/04/05)
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- Catalyst and additive free 6-endo-dig cyclization of ortho-alkynylarylaldimines in water: An environmentally friendly access to isoquinolines
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A novel and sustainable route for the synthesis of isoquinoline was developed by reacting 2-ethynylbenzaldehyde with ammonium hydroxide in water. This method provides a convenient, atom-economical, and catalyst-free access to diversely substituted isoquinolines with moderate to good yields.
- Yang, Jin,Wei, Xinyu,Yu, Yajun,Zhu, Yeting,Zhao, Yun-Hui,Xie, Wenlin,Zhao, Lang
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supporting information
(2019/12/09)
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- Hydrophilic Pd-phosphines catalyzed one-pot synthesis of substituted isoquinolines, furopyridines and thienopyridines in aqueous medium
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A first example of simple and efficient hydrophilic Pd-phosphine complexes catalyzed one-pot three-component reaction of ortho-bromo aldehydes, terminal alkynes and ammonium acetate proceeds through the tandem coupling-imination-annulation path for the synthesis of substituted isoquinolines, furopyridines and thienopyridines in good to excellent yields in green aqueous medium at mild temperature was described.
- Guguloth, Veeranna,Thirukovela, Narasimha Swamy,Balaboina, Ramesh,Paidakula, Suresh,Vadde, Ravinder
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p. 297 - 299
(2019/01/04)
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- An efficient approach to isoquinoline via AgNO3-promoted 6-endo-dig cyclization followed by oxidative elimination of o-alkynylarylaldimines and its application in fluoride recognition
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A novel 6-endo-dig cyclization followed by oxidation/elimination of o-alkynylarylaldimines with 4-hydroxybenzylamine was developed for preparation of isoquinolines. The intermediates of this tandem reaction were monitored by mass spectroscopy (MS) to confirm the reaction pathway. This methodology was further applied to the design and synthesis of a novel ratiometric chemosensor for determination of fluoride.
- Tang, Yongxing,Yu, Yajun,Wei, Xinyu,Yang, Jin,Zhu, Yeting,Zhao, Yun-Hui,Tang, Zilong,Zhou, Zhihua,Li, Xiaofang,Yu, Xianyong
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supporting information
(2019/09/30)
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- Method for synthesizing isoquinoline compound
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The invention discloses a method for synthesizing an isoquinoline compound. The isoquinoline compound is shown in formula I, wherein R1 is hydrogen, a halogen atom, an alkyl, an alkoxy or an amino, and R2 is hydrogen, a halogen atom, an alkyl, an alkoxy or an amino. According to the invention, o-alkynyl aldehyde and p-hydroxybenzylamine are used as raw materials to synthesize a target product through series reactions of imidization, cyclization and oxidation elimination, the method for synthesizing the isoquinoline compound is simple and rapid, the yield of the target compound is high, and a necessary basis is provided for further researching the compound in formula I or related compounds.
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Paragraph 0014; 0015; 0016; 0017
(2019/05/08)
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- Alkoxide-Catalyzed Hydrosilylation of Cyclic Imides to Isoquinolines via Tandem Reduction and Rearrangement
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An alkoxide-catalyzed hydrosilylation of cyclic imides to isoquinolines was realized via tandem reduction and rearrangement. Using TMSOK as the catalyst and (EtO)2MeSiH as the reductant, a series of cyclic imides containing different functional groups were reduced to the corresponding 3-aryl isoquinolines in moderate to good yields. The scenario of the reaction pathway was supposed to involve the reduction of imides to ω-hydroxylactams, which underwent rearrangement in the presence of a base catalyst, and then the carbonyl reduction, followed by siloxy elimination.
- Wu, Xiaoyu,Ding, Guangni,Yang, Liqun,Lu, Wenkui,Li, Wanfang,Zhang, Zhaoguo,Xie, Xiaomin
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p. 5610 - 5613
(2018/09/12)
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- Highly Regioselective Isoquinoline Synthesis via Nickel-Catalyzed Iminoannulation of Alkynes at Room Temperature
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A simple and cost-efficient nickel catalytic system for the annulation of 2-haloaldimines with alkynes to synthesize 3,4-disubstituted and 3-substituted isoquinolines at room temperature has been developed. The air-stable and inexpensive Ni(dppe)Cl2 was employed as a precatalyst, and Et3N was found to be an essential additive for obtaining high yields. By using this nickel catalytic system one-pot three-component direct synthesis of isoquinolines starting with simple 2-halobenzaldehydes, tert-butylamine, and alkynes were also achieved. These reactions occur in moderate to excellent yields with complete regioselectivity. Moreover, these reactions feature a broad substrate scope, easy scalability, operational simplicity, and excellent practicality.
- Sun, Jian-Guo,Zhang, Xiao-Yu,Yang, Hua,Li, Ping,Zhang, Bo
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p. 4965 - 4969
(2018/09/25)
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- Organometallic complex and light-emitting device
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The invention relates to the technical field of organic light-emitting materials, in particular to an organometallic complex material adopting a 3-phenylisoquinoline structure and a light-emitting device. The organometallic complex is selected from at least one of compounds shown as a general formula I. The organometallic complex is a red light-emitting material, and has the technical advantages of a wide main emission peak wavelength range, high light-emitting efficiency and high color purity.
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Paragraph 0236; 0238-0240
(2018/07/30)
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- Study on the iodine-catalyzed reaction of 3-aminopyrazine-2-carbohydrazide and 2-(arylethynyl)benzaldehydes
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At 60 °C in DMSO, the iodine-catalyzed reaction of 3-aminopyrazine-2-carbohydrazide and 2-(arylethynyl)benzaldehydes led hydrazones. Increasing the reaction temperature to 100 °C, the amino and amido still indicated inactive, only the imine took part in the addition of acetylene bond to give 2-arylisoquinolines in high yields with the cleavage of N-N bond unexpectedly under metal-free conditions.
- Pan, Wan-Chen,Liu, Jian-Quan,Wang, Xiang-Shan
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p. 1468 - 1475
(2018/02/19)
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- One substrate, two modes of C-H functionalization: A metal-controlled site-selectivity switch in C-H arylation reactions
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A unique site-selectivity switch has been achieved in the ruthenium-catalyzed C-H arylation reaction of N-acetyl-1,2-dihydroisoquinolines. This metal-mediated switch is antipodal to the previous report on the palladium-mediated C-4 C-H arylation on the same substrate. Mechanistic details reveal interesting aspects of the reaction pathway, and kinetic studies bring out the difference in the modes of C-H activation adopted by the two catalytic systems.
- Tiwari, Virendra Kumar,Kamal, Neha,Kapur, Manmohan
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p. 262 - 265
(2017/11/27)
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- Cobalt-Catalyzed ortho-C?H Functionalization/Alkyne Annulation of Benzylamine Derivatives: Access to Dihydroisoquinolines
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A practical picolinamide-directed C?H functionalization/alkyne annulation of benzylamine derivatives enabling access to the previously elusive 1,4-dihydroisoquinoline skeleton was developed using molecular O2 as the sole oxidant and Co(OAc)2 as precatalyst. The method is compatible with both internal and terminal alkynes and shows high versatility and functional-group tolerance. Furthermore, full preservation of enantiopurity is observed when using non-racemic α-substituted benzylamine derivatives. Kinetic analysis of the reagents and catalyst, labeling experiments, and the isolation and identification of catalytically competent Co-complexes revealed important insights about the mechanism.
- Martínez, ángel Manu,Rodríguez, Nuria,Gómez-Arrayás, Ramón,Carretero, Juan C.
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p. 11669 - 11676
(2017/08/30)
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- Silver Nitrate Mediated Cyclization/N-N Bond-Cleavage Reaction for the Synthesis of 3-Arylisoquinolines
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An unprecedented silver nitrate mediated novel transformation of aromatic hydrazones into various isoquinolines has been developed. This method involves a silver nitrate promoted cyclization of aromatic hydrazones followed by N-N bond cleavage, and has wide substrate scope under mild conditions.
- Zhao, Yun-Hui,Li, Yubo,Luo, Mingjian,Tang, Zilong,Deng, Keqin
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supporting information
p. 2597 - 2600
(2016/11/11)
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- Efficient Synthesis of Isoquinolines by AgNO3-Catalyzed Sequential Imination-Annulation of 2-Alkynyl Aldehydes with Ammonium Bicarbonate
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An operationally simple approach for the tandem synthesis of isoquinolines by the reaction of o-alkynylaldehydes with ammonium bicarbonate via Ag-catalyzed 6-endo-dig ring closure is described. The reaction conditions and the scope of the reaction are examined, and a variety of substituted isoquinolines are prepared in moderate to excellent yields.
- Zhao, Yunhui,Luo, Mingjian,Li, Yubo,Liu, Xiong,Tang, Zilong,Deng, Keqin,Zhao, Gang
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supporting information
p. 857 - 860
(2016/09/20)
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- Method for synthesizing isoquinoline compound
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The invention discloses a method for synthesizing an isoquinoline compound. The isoquinoline compound is as shown in the formula I, wherein R1 is hydrogen, a halogen atom, an alkyl group, an alkoxy group or an amino group, and R2 is hydrogen, a halogen atom, an alkyl group, an alkoxy group or an amino group. The target product is synthesized through two-step reaction, and the synthesizing method is simple and quick and accords with atom economy. Besides, the yield of the target compound is high, and necessary bases are provided for further researching the compound in the formula I or relevant compounds. Please see the molecular formula of the compound in the description.
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Paragraph 0032; 0033; 0034
(2016/10/31)
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- A room-temperature protocol to access isoquinolines through Ag(i) catalysed annulation of o-(1-alkynyl)arylaldehydes and ketones with NH4OAc: Elaboration to berberine and palmatine
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An efficient and mild protocol for the direct construction of aryl- and alkyl-substituted isoquinolines has been realized through silver nitrate catalyzed aromatic annulation of o-(1-alkynyl)arylaldehydes and ketones with ammonium acetate. The salient feature of this methodology is that this annulation could be effected at room temperature leading to a wide range of isoquinoline derivatives in good to excellent yields. Additionally, this approach has been employed to the synthesis of biologically important isoquinoline alkaloids such as berberine and palmatine.
- Reddy, Virsinha,Jadhav, Abhijeet S.,Vijaya Anand, Ramasamy
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p. 3732 - 3741
(2015/03/30)
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- Efficient synthesis of isoquinolines and pyridines via copper(i)-catalyzed multi-component reaction
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A wide range of 3-substituted isoquinolines, steroidal pyridines, 5,6-dihydrobenzo[f]isoquinolines and 1,6-naphthyridine were synthesized in good yield via a ligand-free copper-catalyzed three-component reaction of β-halovinyl/aryl aldehyde, aromatic/alip
- Shekarrao, Kommuri,Kaishap, Partha Pratim,Gogoi, Sanjib,Boruah, Romesh C.
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p. 14013 - 14023
(2014/04/17)
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- Efficient synthesis of isoquinoline derivatives via AgOTf/Cu(OTf) 2-cocatalyzed cyclization of 2-alkynyl benzaldoxime
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An efficient, AgOTf and Cu(OTf)2 multicatalytic intramolecular cycloisomerization of 2-alkynylbenzaldoxime is reported. Isoquinoline N-oxides have been found to be deoxygenated to the corresponding quinolines in good yields in dimethylformamide/ dichloroethane (v/v 5:1) as solvent at 120 °C. Copyright Taylor & Francis Group, LLC.
- Zhao, Xiaona,Fan, Weidong,Miao, Zhiwei,Chen, Ruyu
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p. 1714 - 1720
(2013/05/21)
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- Facile synthesis of 3-substituted isoquinolines derivatives via microwave-assisted tandem three-component coupling cyclization
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A novel three-component reaction of o-bromobenzaldehyde, terminal alkynes and tert-butyl amine has been established, which proceeded smoothly to give 3-substituted isoquinolines in good yields in the presence of palladium/copper catalysts under microwave irradiation.
- Lin, Long,Wu, Qiongyou,Huang, Shaowei,Yang, Guangfu
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experimental part
p. 1075 - 1082
(2012/08/07)
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- Palladium-catalyzed, microwave-enhanced three-component synthesis of isoquinolines with aqueous ammonia
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A variety of substituted isoquinoline derivatives can be synthesized in moderate yield by a palladium-catalyzed, microwave-assisted MCR starting from o-bromoarylaldehydes, terminal alkynes, and aqueous ammonia. Georg Thieme Verlag Stuttgart New York.
- Dellacqua, Monica,Abbiati, Giorgio,Rossi, Elisabetta
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scheme or table
p. 2672 - 2676
(2010/11/24)
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- Microwave-promoted synthesis of N-heterocycles by tandem imination/ annulation of γ- and δ-ketoalkynes in the presence of ammonia
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The synthesis of 3-substituted l-methylpyrrolo[l,2-a]pyrazines and 3-substituted isoquinolines was achieved by the intramolecular cyclisation of 2-acetyl-l-propargylpyrroles and 2-alkynylbenzaldehydes, respectively, in the presence of ammonia under microwave heating. The tandem imination/annulation of 2-alkynylbenzaldehydes was easily accomplished under standard conditions, while TiCl4 was used to achieve pyrrolo[l,2-a]pyrazines. The reaction mechanism and the regioselectivity were discussed on the basis of theoretical calculations and spectroscopic data. Wiley-VCH Verlag GmbH & Co. KGaA.
- Alfonsi, Maria,Dell'Acqua, Monica,Facoetti, Diego,Arcadi, Antonio,Abbiati, Giorgio,Rossi, Elisabetta
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experimental part
p. 2852 - 2862
(2009/09/06)
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