53503-30-3Relevant academic research and scientific papers
Cascade Reaction of α, β-Unsaturated Ketones and 2-Aminoaryl Alcohols for the Synthesis of 3-Acylquinolines by a Copper Nanocatalyst
Liu, Yuan,Wang, Chen,Tong, Yixin,Ling, Yong,Zhou, Changjian,Xiong, Biao
supporting information, p. 4422 - 4429 (2021/08/07)
3-Acylquinolines possess widespread applications in functional chemicals. However, the convenient and selective synthesis of such important substructures has to date remained a challenge. Herein, we report a method to access 3-acylquinolines from α, β-unsaturated ketones and 2-aminoaryl alcohols in one pot with a copper nanocatalyst supported on nitrogen-silica-doped carbon (Cu/N?SiO2?C). Mechanistically, the construction of the product involves a cascade procedure including radical-type oxidation of 2-aminoaryl alcohols, aza-Michael addition and annulation. This developed protocol proceeds with merits of mild reaction conditions, good functional group tolerance, earth-abundant and reusable copper catalyst, easily available stocks and O2 as the sole oxidant, which provides an alternative way for the sustainable synthesis of quinoline derivatives. (Figure presented.).
Synthesizing method of aromatic pyridinopyridine compound
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Paragraph 0111; 0112; 0113, (2017/07/20)
The invention discloses a synthesizing method of an aromatic pyridinopyridine compound, and belongs to the technical field of organic synthesizing. According to the technical scheme, the characteristics of the synthesizing method refers to the description. The method is simple, efficient, convenient to operate, mild in conditions, and wide in substrate applying scope.
α,β-Functionalization of saturated ketones with anthranils: Via Cu-catalyzed sequential dehydrogenation/aza-Michael addition/annulation cascade reactions in one-pot
Tiweri, Dipak Kumar,Phanindrudu, Mandalaparthi,Wakade, Sandip Balasaheb,Nanubolu, Jagadeesh Babu,Tiwari, Dharmendra Kumar
supporting information, p. 5302 - 5305 (2017/07/10)
An efficient method to access functionalized quinolines from the readily available saturated ketones and anthranils has been explored. This one-pot cascade reaction involves the in situ generation of α,β-unsaturated ketones by the copper catalysed dehydro
Copper-Catalyzed Aerobic Oxidative Carbocyclization Reactions of N -[(E)-Stilben-2-yl]amine Derivatives
Lu, Cheng-Yen,Chuang, Che-Ping
, p. 3687 - 3700 (2015/11/28)
A synthetic method for highly functionalized 2-quinolinones and quinolines has been developed. The copper(II)-catalyzed aerobic oxidative carbocyclization reactions of α-substituted N-[(E)-stilben-2-yl]acetamides, via the intramolecular carbocupration onto the alkenyl moiety, produced 3-substituted 2-quinolinones. Several useful functional groups including benzoyl, acetyl, cyano, and ethoxycarbonyl groups are compatible with the reaction conditions. This strategy was further applied to N-[(E)-stilben-2-yl]enamines to prepare 2,3-disubstituted quinolines in good yields.
Manganese(III) acetate mediated oxidative radical cyclizations of N -(2-alkenylaryl)-substituted enamines
Tsai, Pei-Ju,Kao, Chih-Bo,Chiow, Wan-Ru,Chuang, Che-Ping
, p. 175 - 182 (2014/03/21)
A method has been developed for the synthesis of highly functionalized quinolines from readily available N-(2-alkenylaryl)-substituted enamines via a 6-exo-trig radical cyclization of an imine radical. Several useful functional groups including morpholinocarbonyl, benzoyl, and cyano, are compatible with the reaction conditions. Under the Mn(II)/Co(II)/O2 redox system, these N-(2-alkenylaryl)enamines were also converted into the corresponding quinolines effectively. This strategy was further applied to related 1,4-naphthoquinone derivatives, and benzo[b]acridine-6,11-diones were formed in good yields.
Iron/acetic acid mediated intermolecular tandem C-C and C-N bond formation: An easy access to acridinone and quinoline derivatives
Rajawinslin,Gawande, Sachin D.,Kavala, Veerababurao,Huang, Yi-Hsiang,Kuo, Chun-Wei,Kuo, Ting-Shen,Chen, Mei-Ling,He, Chiu-Hui,Yao, Ching-Fa
, p. 37806 - 37811 (2014/11/07)
An efficient iron/acetic acid mediated one pot reductive cyclization protocol was successfully developed for the synthesis of acridinone and quinoline derivatives. This highly efficient process proceeds under mild conditions, tolerates different functiona
A highly regioselective Friedl?nder reaction mediated by lanthanum chloride
Chen, Ying,Huang, Jinkun,Hwang, Tsang-Lin,Li,Cui, Sheng,Chan, Johann,Bio, Matthew
experimental part, p. 3237 - 3241 (2012/07/31)
A highly efficient and regioselective Friedl?nder reaction of unsymmetrical 1,3-diketones with 2-aminoaryl aldehydes (ketones) is described. The methodology leads to the synthesis of a broad scope of substituted quinolines in high yield and excellent regioselectivity.
Synthesis of quinolines via friedlaender reaction in water and under catalyst-free conditions
Shen, Qiang,Wang, Limin,Yu, Jianjun,Liu, Mingtao,Qiu, Jun,Fang, Lei,Guo, Fenglou,Tang, Jun
supporting information; experimental part, p. 389 - 392 (2012/03/11)
A straightforward and efficient method for the synthesis of quinolines via Friedlaender reaction of 2-aminobenzaldehyde with various ketones or malononitrile in water without using any catalyst at 70 °C is reported. Georg Thieme Verlag Stuttgart New York.
Selective reduction of nitroarenes by a Hantzsch 1,4-dihydropyridine: A facile and efficient approach to substituted quinolines
Xing, Rui-Guang,Li, Ya-Nan,Liu, Qiang,Han, Yi-Feng,Wei, Xia,Li, Jing,Zhou, Bo
, p. 2066 - 2072 (2011/08/05)
An efficient reductive cyclization of o-nitrocinnamoyl compounds was achieved by employing a Hantzsch 1,4-dihydropyridine ester as a biomimetic reducing agent in the presence of catalytic palladium on carbon. This approach was successfully applied to the synthesis of substituted quinolines. Georg Thieme Verlag Stuttgart ? New York.
