1198-30-7Relevant articles and documents
A PASE-based approach towards 12-(1H-1,2,3-triazol-1-yl)-indolo[2,1-a]isoquinolines via the reaction of 3-(isoquinolin-1-yl)-1,2,4-triazines with benzyne
Gundala, Sravya,Guda, Mallikarjuna Reddy,Khasanov, Albert F.,Kopchuk, Dmitry S.,Krinochkin, Alexey P.,Santra, Sougata,Zyryanov, Grigory V.,Venkatapuram, Padmavathi,Garcia, Jarem Raul,Charushin, Valery N.
, p. 369 - 371 (2019)
12-(1H-1,2,3-Triazol-1-yl)indolo[2,1-a]isoquinolines are prepared in 51–56% yields using a PASE (pot, atom, step, economic)-based approach, namely, by the reaction between available 5-R-6-Ar-3-(isoquinolin-1-yl)-1,2,4-triazines and in situ generated benzyne. A mechanism comprising domino-transformation was suggested, and the structure of one key product was confirmed by a single crystal X-ray diffraction analysis.
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Izzo,Kende
, p. 5731,5733 (1966)
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Studies on tertiary amine oxides. LXIII. Nitration of 1-cyanoisoquinoline 2-oxide and isoquinoline 2-oxide
Saito,Hamana
, p. 23 - 29,24, 25, 27, 28 (1979)
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Highly chemoselective deoxygenation of N-heterocyclic: N -oxides under transition metal-free conditions
Kim, Se Hyun,An, Ju Hyeon,Lee, Jun Hee
supporting information, p. 3735 - 3742 (2021/05/04)
Because their site-selective C-H functionalizations are now considered one of the most useful tools for synthesizing various N-heterocyclic compounds, the highly chemoselective deoxygenation of densely functionalized N-heterocyclic N-oxides has received much attention from the synthetic chemistry community. Here, we provide a protocol for the highly chemoselective deoxygenation of various functionalized N-oxides under visible light-mediated photoredox conditions with Na2-eosin Y as an organophotocatalyst. Mechanistic studies imply that the excited state of the organophotocatalyst is reductively quenched by Hantzsch esters. This operationally simple technique tolerates a wide range of functional groups and allows high-yield, multigram-scale deoxygenation. This journal is
Metal-free, redox-neutral, site-selective access to heteroarylamine via direct radical?radical cross-coupling powered by visible light photocatalysis
Zhou, Chao,Lei, Tao,Wei, Xiang-Zhu,Ye, Chen,Liu, Zan,Chen, Bin,Tung, Chen-Ho,Wu, Li-Zhu
supporting information, p. 16805 - 16813 (2020/11/09)
Transition-metal-catalyzed C?N bond-forming reactions have emerged as fundamental and powerful tools to construct arylamines, a common structure found in drug agents, natural products, and fine chemicals. Reported herein is an alternative access to heteroarylamine via radical?radical cross-coupling pathway, powered by visible light catalysis without any aid of external oxidant and reductant. Only by visible light irradiation of a photocatalyst, such as a metal-free photocatalyst, does the cascade single-electron transfer event for amines and heteroaryl nitriles occur, demonstrated by steady-state and transient spectroscopic studies, resulting in an amine radical cation and aryl radical anion in situ for C?N bond formation. The metal-free and redox economic nature, high efficiency, and site-selectivity of C?N cross-coupling of a range of available amines, hydroxylamines, and hydrazines with heteroaryl nitriles make this protocol promising in both academic and industrial settings.
Regioselective Cyanation of Six-Membered N-Heteroaromatic Compounds Under Metal-, Activator-, Base- and Solvent-Free Conditions
Sarmah, Bikash Kumar,Konwar, Monuranjan,Bhattacharyya, Dipanjan,Adhikari, Priyanka,Das, Animesh
supporting information, p. 5616 - 5625 (2019/11/22)
A regioselective cyanation of heteroaromatic N-oxides with trimethylsilyl cyanide has been developed to obtain 2-substituted N-heteroaromatic nitrile without the requirement of any external activator-, metal-, base-, and solvent. The present protocol is a straightforward, one-pot heteroaromatic C?H cyanation process, and proceeds smoothly in conventional heating but also under microwave irradiation with shorter reaction times. This approach now allows access to a broad class of quinoline N-oxides and other heteroarene N-oxides with high to good yields and can also be scaled up to obtain gram quantities. Further application of this process was observed and utilized in late-stage cyanation of the anti-malarial drug quinine as well as transformation of the 2-cyanoazines to a series of biologically important molecules. Based on the experimental observations, a plausible mechanism has also been proposed highlighting the dual role of trimethylsilyl cyanide as a nitrile source and as an activating agent. (Figure presented.).