30081-56-2Relevant academic research and scientific papers
Benzyne-mediated rearrangement of 3-(2-pyridyl)-1,2,4-triazines into 10-(1H-1,2,3-triazol-1-yl)pyrido[1,2-a]indoles
Nikonov, Igor L.,Kopchuk, Dmitry S.,Kovalev, Igor S.,Zyryanov, Grigory V.,Khasanov, Albert F.,Slepukhin, Pavel A.,Rusinov, Vladimir L.,Chupakhin, Oleg N.
, p. 6427 - 6429 (2013)
The reaction between 5-R-6-R1-3-(2-pyridyl)-1,2,4-triazines and benzyne generated in situ in toluene under reflux results in the formation of 10-(1H-1,2,3-triazol-1-yl)pyrido[1,2-a]indoles 3 in up to 60% yields instead of the expected 3-R-4-R1-1-(2-pyridyl)isoquinolines 2. The crystal structure of product 3c and the proposed mechanism for the formation of 3 are reported.
Rh(III)?catalyzed synthesis of isoquinolines from N-hydroxyoximes and alkynes in γ-valerolactone
Jiang, Kuan-Chang,Wang, Liang,Chen, Qun,He, Ming-Yang,Shen, Ming-Gui,Zhang, Zhi-Hui
supporting information, p. 94 - 102 (2020/09/21)
A Rh (III)?catalyzed synthesis of isoquinoline derivatives from N-hydroxyoximes and alkynes via C–H activation/annulation process in biomass-derived γ-valerolactone (GVL) has been developed. A series of functional groups were well tolerated, affording the desired products in good to excellent yields.
Ruthenaelectro-Catalyzed Domino Three-Component Alkyne Annulation for Expedient Isoquinoline Assembly
Tan, Xuefeng,Hou, Xiaoyan,Rogge, Torben,Ackermann, Lutz
supporting information, p. 4619 - 4624 (2021/02/05)
The electrochemical three-component assembly of isoquinolines has been accomplished by ruthenaelectro-catalyzed C?H/N?H functionalization. The robustness of the electrocatalysis was reflected by an ample substrate scope, an efficient electrooxidation, and an operationally friendly procedure. The isolation of key intermediates and detailed mechanistic studies, including unprecedented cyclovoltammetric analysis of a seven-membered ruthenacycle, provided support for an unusual ruthenium(II/III/I) regime.
Eco-friendly synthesis method of 3, 4-disubstituted isoquinoline derivative promoted by room-temperature illumination
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Paragraph 0015, (2020/05/02)
The invention discloses an eco-friendly synthesis method of a 3, 4-disubstituted isoquinoline derivative promoted by room-temperature illumination. The method comprises the following steps: by using water and polyethylene glycol 400 as a mixed solvent and a phenyl oxime compound and non-terminal alkyne as raw materials, synthesizing the 3, 4-disubstituted isoquinoline derivative at a room temperature under illumination. The method is a C-H coupling reaction catalyzed by a transition metal, and eco-friendly synthesis of the isoquinoline derivative can be simply and efficiently carried out. Compared with a traditional method, the method is safer, more economical and environmentally friendly, the functional group tolerance is good, the yield is high, extra photocatalysts and oxidizing agentsare not needed, the cost is reduced, the byproduct is H2O, the generation of a large amount of wastes is avoided, the atom utilization rate is improved, the substrate does not need to be pre-activatedand the reaction is carried out at room temperature, and the operation difficulty is reduced. According to the invention, a derivative molecular library of an isoquinoline ring with biological activity can be simply and rapidly supplemented, so that screening and discovery of new drug candidate molecules are facilitated.
Rh(III)-catalyzed synthesis of isoquinolines using the N-Cl bond of N-chloroimines as an internal oxidant
Chu, Benfa,Fang, Lili,Guo, Shan,Qi, Bing,Shi, Pengfei,Wang, Qi,Zhu, Jin
supporting information, (2020/03/10)
The Rh(III)-catalyzed coupling of N-chloroimines with alkynes for the efficient synthesis of isoquinolines is reported. This represents the first use of the N-Cl bond of N-chloroimines as an internal oxidant for construction of the isoquinoline skeleton. The synthesis features atom and step economy, a green solvent (EtOH), mild reaction conditions, and a broad substrate scope.
Hydroxylamine-O-Sulfonic Acid (HOSA) as a Redox-Neutral Directing Group: Rhodium Catalyzed, Additive Free, One-Pot Synthesis of Isoquinolines from Arylketones
Biswal, Pragati,Pati, Bedadyuti Vedvyas,Chebolu, Rajesh,Ghosh, Asit,Ravikumar
, p. 1006 - 1014 (2020/02/15)
A new application of hydroxylamine-O-sulfonic acid (HOSA) has been discovered whereby aromatic ketones react with HOSA and alkynes to form isoquinolines in the presence of a RhIII catalyst. This C–H/N–O annulation methodology gives excellent yields even without any silver additive, acid/base or metal oxidant. This is the first report wherein a directing group is simultaneously forming in situ, acting as acid additive, and also as an internal oxidant.
Easy access to synthesize isoquinolines from aryl ketoximes and internal alkynes via Iridium (III)-catalyzed C[sbnd]H/N[sbnd]O bond activation
Lin, Wei,Hu, Xiu-Xiu,Zhuang, Cang-Wei,Wang, Ya-Zhen
, p. 3015 - 3023 (2019/04/30)
A highly efficient approach to synthesize isoquinoline derivatives through Iridium(III)-catalyzed cyclization of aryl ketoximes and internal alkynes without oxidant is reported. A broad range isoquinolines are obtained in good to excellent yields and various functional groups are well tolerated.
Ruthenium-Catalyzed Annulation of N -Cbz Hydrazones via C-H/N-N Bond Activation for the Rapid Synthesis of Isoquinolines
Bhanage, Bhalchandra M.,Deshmukh, Dewal S.
, p. 2506 - 2514 (2019/06/08)
In this work, N -Cbz hydrazone has been employed as a rarely explored directing group for the synthesis of isoquinolines by annulation with internal alkynes via C-H/N-N activation using Ru catalyst. Additive as well as external oxidant-free rapid protocol
Cp*Co(III) catalyzed annulation of N-Cbz hydrazones for the redox-neutral synthesis of isoquinolines via C–H/N–N bond activation
Subhedar, Dnyaneshwar D.,Deshmukh, Dewal S.,Bhanage, Bhalchandra M.
, p. 3121 - 3130 (2019/08/30)
A new cascade oxidative cyclization reaction of N-Cbz hydrazones with internal alkynes has been explored for the preparation of isoquinoline derivatives using Cp*CoIII-catalyst through C–H and N–N bond functionalization. N-Cbz hydrazones are ra
Cp?-Free Cobalt-Catalyzed C-H Activation/Annulations by Traceless N, O-Bidentate Directing Group: Access to Isoquinolines
Li, Xiao-Cai,Du, Cong,Zhang, He,Niu, Jun-Long,Song, Mao-Ping
supporting information, p. 2863 - 2866 (2019/04/17)
N,O-Bidentate directing-enabled, traceless heterocycle synthesis is described via Cp?-free cobalt-catalyzed C-H activation/annulation. The weakly coordinating nature of the carboxylic acid was employed for the preparation of isoquinolines. Meanwhile, the N-O bond of the α-imino-oxy acid can serve as an internal oxidant. Terminal as well as internal alkynes can be efficiently applied to the catalytic system. This operationally simple approach shows a broad substrate scope with the products obtained in good to excellent yields.
