111293-91-5Relevant academic research and scientific papers
Cobalt-Mediated Decarboxylative/Desilylative C?H Activation/Annulation Reaction: An Efficient Approach to Natural Alkaloids and New Structural Analogues
Chen, Kang,Lv, Shan,Lai, Ruizhi,Yang, Zhongzhen,Hai, Li,Nie, Ruifang,Wu, Yong
, (2022/02/03)
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
Silver/Rhodium Relay Catalysis Enables C?H Functionalization of In Situ Generated Isoquinolines with Sulfoxonium Ylides: Construction of Hexahydrodibenzo[a,g]quinolizine Scaffolds
Li, Quanzhe,Liu, Ruixing,Wei, Yin,Shi, Min
, p. 2664 - 2669 (2021/04/05)
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.).
Alkoxide-Catalyzed Hydrosilylation of Cyclic Imides to Isoquinolines via Tandem Reduction and Rearrangement
Wu, Xiaoyu,Ding, Guangni,Yang, Liqun,Lu, Wenkui,Li, Wanfang,Zhang, Zhaoguo,Xie, Xiaomin
, p. 5610 - 5613 (2018/09/12)
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.
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
Reddy, Virsinha,Jadhav, Abhijeet S.,Vijaya Anand, Ramasamy
, p. 3732 - 3741 (2015/03/30)
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.
An efficient synthesis of 3-substituted isoquinoline and pyridine derivatives by gold catalyzed intramolecular cyclization from o-alkynyloximes
Subbarao,Reddy, G. Raveendra,Muralikrishna,Reddy
, p. 1045 - 1050 (2014/08/05)
A one-pot reaction was developed efficiently by AuCl3 catalyzed intramolecular cyclization of aromatic o-alkynyloximes and 2-alkynylcycloalkene- 1-carbaldoximes leading to the formation of isoquinoline and pyridine derivatives with high yields. This methodology has been applied for aromatic as well as aliphatic systems. Aromatic o-alkynyloximes are benzene and naphthalene, whereas electron-donating groups are 4-methoxybenzene, 4-methylbenzene, and 4-methoxy-5-methylbenzene. There are electron-withdrawing groups such as chloro and nitrobenzene o-alkynyl oximes, and the same methodology has been successfully applied to pyridine and piperonal, which is also extended to aliphatic rings such as five-member, six-member, seven-member, and eight-member 2-alkynylcycloalkene-1-carbaldoximes.
One-pot synthesis of isoquinoline and related compounds via Cu-mediated tandem cross-coupling and cyclization
Dhara, Shubhendu,Singha, Raju,Nuree, Yasin,Ray, Jayanta K.
supporting information, p. 795 - 798 (2014/02/14)
One-pot synthetic strategy has been developed to access isoquinolines and its analogs via Cu-mediated tandem cross-coupling and cyclization in good yields under mild reaction conditions. A mixture of suitably substituted α-bromoaldehyde, terminal alkyne, and aq NH3 in CuI/1,10-phenanathroline catalytic system afforded the 3-substituted isoquinoline regio-selectively in good to excellent yields.
