860190-32-5Relevant academic research and scientific papers
Eco-efficient synthesis of 2-quinaldic acids from furfural
Li, Minghao,Dong, Xiaohan,Zhang, Na,Jér?me, Fran?ois,Gu, Yanlong
supporting information, p. 4650 - 4655 (2019/09/09)
Quinaldic acids are important fine chemicals. Nowadays, industrial methods to synthesize quinaldic acids rely heavily on a three-step process established based on the Reissert reaction, which involves however the use of highly toxic potassium cyanide. In this paper, a novel cyclization of aniline with ethyl 4,4-diethoxycrotonate was realized, which offered ethyl quinaldate in good yield. Based on this reaction, an eco-efficient method to prepare quinaldic acids was developed, which involves the following three steps: (i) synthesis of ethyl 4,4-diethoxycrotonate through photooxidation of furfural and a consecutive ring-opening alcoholysis; (ii) cyclization of ethyl 4,4-diethoxycrotonate with aniline, and (iii) hydrolysis of the generated ethyl quinaldate. This new method not only avoids the use of toxic potassium cyanide but also meets many salient features of green chemistry, such as the use of bio-based feedstocks, environmentally benign metal-free conditions and good reaction yields.
Copper-catalysed aerobic oxidative esterification of N-heteroaryl methanes with alcohols
Liu, Min,Chen, Tieqiao,Yin, Shuang-Feng
, p. 690 - 693 (2016/02/18)
Efficient copper-catalysed aerobic oxidative esterification of N-heteroaryl methanes with alcohols has been developed. A variety of N-heteroaryl esters including those with functional groups are produced in good to excellent yields under the present reaction conditions.
Copper-catalyzed [5 + 1] annulation of 2-ethynylanilines with an N, O -acetal leading to construction of quinoline derivatives
Sakai, Norio,Tamura, Kosuke,Shimamura, Kazuyori,Ikeda, Reiko,Konakahara, Takeo
, p. 836 - 839 (2012/04/05)
A novel copper-catalyzed [5 + 1] annulation of 2-ethynylanilines with an N,O-acetal, which functioned as a C1 part, leading to the preparation of quinoline derivatives with an ester substituent on the 2-position is described. A combination of CuBr2/
Radical cation salt induced Povarov reaction between iminoethyl glyoxylate and N-vinylamides: Synthesis of quinoline-2-carboxylate derivatives
Jia, Xiaodong,Qing, Chang,Huo, Congde,Peng, Fangfang,Wang, Xicun
supporting information, p. 7140 - 7142 (2013/01/15)
A domino process between iminoethyl glyoxylate and N-vinylamides was achieved under the catalytic radical cation salt induced conditions, producing a series of quinoline-2-carboxylates. N-Vinylamides were involved as an acetylene equivalent. A possible mechanism was proposed to rationalize the formation of the products.
