1436-43-7Relevant articles and documents
Corrigendum: Organo-Photoredox Catalyzed Oxidative Dehydrogenation of N-Heterocycles (Chemistry - A European Journal, (2017), 23, 57, (14167-14172), 10.1002/chem.201703642)
Sahoo, Manoj K.,Jaiswal, Garima,Rana, Jagannath,Balaraman, Ekambaram
, p. 7038 - 7038 (2019)
The authors have been alerted to an error that was unfortunately missed at the time of publication. Table was duplicated with Table 4. The correct version of Table 2 is shown below. The authors apologise for any inconvenience caused. Organo-photoredox catalyzed oxidative dehydrogenation of tetrahydroquinolines (THQ).[a,b] (Table presented.) [a] Reaction conditions: 1 (0.5 mmol), rose bengal (1.0 mol %), N,N-dimethylacetamide (2.0 mL), open air atmosphere under visible-light irradiation at room temperature for 24 h. [b] Isolated yields. [c] 0.1 mol % of photoredox catalyst for 28 h.
Structure-function studies on a synthetic guanosine receptor that simultaneously binds Watson-Crick and Hoogsteen sites
Quinn, Jordan R.,Zimmerman, Steven C.
, p. 7459 - 7467 (2005)
A series of receptors (11-16) designed to simultaneously bind the Watson-Crick and Hoogsteen sites of guanosine were synthesized, and their binding of guanosine tri-O-pentanoate (32) was probed via 1H NMR complexation studies in 5% DMSO-d6-chloroform-d. The guanosine receptors were synthesized with aminonaphthalene or aminoquinoline auxiliary groups tethered to N-4 of cytosine via a methylene or carbonyl group. A structure-function relationship was established allowing energetic contributions made by components of nucleoside analogues to be probed and more general design rules formulated that may guide the development of more efficacious DNA bases.
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Hata et al.
, p. 2286 (1971)
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Regioselective direct oxidative C-H cyanation of quinoline and its derivatives catalyzed by vanadium-containing heteropoly acids
Yamaguchi, Kazuya,Xu, Ning,Jin, Xiongjie,Suzuki, Kosuke,Mizuno, Noritaka
, p. 10034 - 10037 (2015)
A direct oxidative C-H cyanation of quinoline and its derivatives using trimethylsilyl cyanide as the cyano source and molecular oxygen as the terminal oxidant has been developed. In the presence of catalytic amounts of vanadium-containing heteropoly acids, e.g., H7PV4Mo8O40, cyanation of various quinoline and its derivatives preferentially took place at the 4-position, affording the corresponding substituted 4-cyanoquinolines as the major products.
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
Cascade Process for Direct Transformation of Aldehydes (RCHO) to Nitriles (RCN) Using Inorganic Reagents NH2OH/Na2CO3/SO2F2 in DMSO
Fang, Wan-Yin,Qin, Hua-Li
, p. 5803 - 5812 (2019/05/14)
A simple, mild, and practical process for direct conversion of aldehydes to nitriles was developed feathering a wide substrate scope and great functional group tolerability (52 examples, over 90% yield in most cases) using inorganic reagents (NH2OH/Na2CO3/SO2F2) in DMSO. This method allows for transformations of readily available, inexpensive, and abundant aldehydes to highly valuable nitriles in a pot, atom, and step-economical manner without transition metals. This protocol will serve as a robust tool for the installation of cyano-moieties to complicated molecules.
Hypervalent Iodine(III)-Mediated Regioselective Cyanation of Quinoline N-Oxides with Trimethylsilyl Cyanide
Xu, Feng,Li, Yuqin,Huang, Xin,Fang, Xinjie,Li, Zhuofei,Jiang, Hongshuo,Qiao, Jingyi,Chu, Wenyi,Sun, Zhizhong
, p. 520 - 525 (2018/12/13)
A regioselective cyanation of quinoline N-oxides with trimethylsilyl cyanide was developed by using (Diacetoxyiodo) benzene (PIDA) as mediated hypervalent iodine(III) reagent under metal-free and base-free reaction conditions to obtain 2-cyanoquinolines. The efficient PIDA reagent could play the role of an activator of the substrates and an accelerator of N?O bond cleavage. The reaction system featured a wide range of substrate suitability and high yields. The procedure was enlarged gram-scale to synthesize the tuberculosis (TB) inhibitor. Finally, according to some experimental results, a plausible mechanism for the cyanation reaction is proposed. (Figure presented.).
