5278-56-8Relevant academic research and scientific papers
Visible-light-driven Cadogan reaction
Qu, Zhonghua,Wang, Pu,Chen, Xing,Deng, Guo-Jun,Huang, Huawen
supporting information, p. 2582 - 2586 (2021/03/09)
Visible-light-driven photochemical Cadogan-type cyclization has been discovered. The organic D-A type photosensitizer 4CzIPN found to be an efficient mediator to transfer energy from photons to the transient intermediate that breaks the barriers of deoxygenation in Cadogan reaction and enables a mild metal-free access to carbazoles and related heterocycles. DFT calculation results indicate mildly endergonic formation of the intermediate complex of nitrobiarenes and PPh3, which corresponds with experimental findings regarding reaction temperature. The robust synthetic capacity of the photoredox Cadogan reaction systems has been demonstrated by the viable productivity of a broad range of carbazoles and related N-heterocycles with good tolerance of various functionalities.
A concise Friedl?nder/Buchwald-Hartwig approach to the total synthesis of quindoline, a bioactive natural indoloquinoline alkaloid, and toward the unnatural 10-methylquindoline
Méndez, María V.,Simonetti, Sebastian O.,Kaufman, Teodoro S.,Bracca, Andrea B. J.
, p. 10803 - 10813 (2019/07/15)
A new approach toward the synthesis of quindoline, a recognized indoloquinoline alkaloid, is reported. The sequence comprises the synthesis of 2-(2-nitrophenyl)quinoline through an optimized Friedl?nder condensation of 2-amino benzaldehyde with 2-nitroacetophenone, followed by the selective C-3 bromination of the quinoline moiety to direct the cyclization, reduction of the nitro group and a final Buchwald-Hartwig cyclization. In addition, quindoline was also converted to the unnatural 10-methylquindoline by reaction with dimethyl carbonate under DBU promotion. It was found that the non-directed reductive cyclization of 2-(2-nitrophenyl)quinoline results in indazolo[2,3-a]quinoline, instead of yielding quindoline. DFT calculations were employed to explain this reaction outcome; this finding suggested that the result of a previously reported total synthesis of quindoline should be revised.
Rhodium(III)-catalyzed azidation and nitration of arenes by C-H activation
Xie, Fang,Qi, Zisong,Li, Xingwei
supporting information, p. 11862 - 11866 (2013/11/19)
Getting a handle on it: In the chelation-assisted title reactions in the presence of a hypervalent iodine oxidant, sodium azide and sodium nitrite served as readily available nitrogen sources, and pyridine, pyrimidine, and pyrazole substituents were effic
Limitations of the two-phase doebner-miller reaction for the synthesis of quinolines
Reynolds, Kristie A.,Young, David J.,Loughlin, Wendy A.
experimental part, p. 3645 - 3648 (2010/12/19)
The Doebner-Miller synthesis of quinolines under modified biphasic conditions was investigated. Crotonaldehyde, reacted readily with aniline to produce 2-methylquinoline. However, cinnamaldehyde and other γ-substituted α,β-unsaturated aldehydes yielded complex mixtures with substituted anilines to provide only trace quantities of quinolines. The Doebner-Miller reaction under these conditions is only suitable for sterically accessible α,β-unsaturated aldehydes.
Synthesis of quinolines by a solid acid-catalyzed microwave-assisted domino cyclization-aromatization approach
De Paolis, Omar,Teixeira, Liliana,T?r?k, Béla
experimental part, p. 2939 - 2942 (2009/07/26)
A microwave-assisted solid acid-catalyzed synthesis of quinolines from anilines and cinnamaldehydes is described. Use of montmorillonite K-10 results in a one-pot process; the cyclization and oxidation steps readily take place in a domino approach. Reactions were completed in a matter of minutes and provided excellent yields. The efficient and ecofriendly catalyst and the convenience of the product isolation make this process an attractive alternative for the synthesis of these important heterocycles.
Thermal cyclization of 3-arylamino-3-(2-nitrophenyl)-propenal Schiff base hydrochlorides followed by triethyl phosphite mediated deoxygenation: A facile synthesis of quindolines
Dutta, Bishnupada,Some, Surajit,Ray, Jayanta K.
, p. 377 - 379 (2007/10/03)
A simple and useful method for the synthesis of various 2-substituted quindolines starting from 2-nitroacetophenone is described.
Synthesis of Indazoloquinolines
Reddy, Y. Padma,Reddy, K. Kondal
, p. 563 - 564 (2007/10/02)
A number of 2-(o-nitrophenyl)quinolines (Ia-e) have been synthesised and converted via amines (IIa-e) into corresponding azides (IIIa-e).Thermolysis and deoxygenation of 2-(o-azidophenyl)-(IIIa-e) and 2-(o-nitrophenyl)-(Ia-e)-quinolines respectively lead
