1197985-25-3Relevant academic research and scientific papers
Base-promoted one-pot synthesis of pyridine derivatives via aromatic alkyne annulation using benzamides as nitrogen source
Ashiq, Muhammad Naeem,Hua, Ruimao,Iqbal, Muhammad Asif,Mehmood, Hina
supporting information, (2021/11/08)
In the presence of Cs2CO3, the first simple, efficient, and one-pot procedure for the synthesis of 3,5-diaryl pyridines via a variety of aromatic terminal alkynes with benzamides as the nitrogen source in sulfolane is described. The formation of pyridine derivatives accompanies the outcome of 1,3-diaryl propenes, which are also useful intermediates in organic synthesis. Thus, pyridine ring results from a formal [2+2+1+1] cyclocondensation of three alkynes with benzamides, and one of the alkynes provides one carbon, whilst benzamides provide a nitrogen source only. A new transformation of alkynes as well as new utility of benzamide are found in this work.
Two C=C Bond Participation in Annulation to Pyridines Based on DMF as the Nonadjacent N and C Atom Donors
Su, Miao-Dong,Liu, Hai-Ping,Cao, Zhong-Zhong,Liu, Yufeng,Li, Hui,Nie, Zhi-Wen,Yang, Tong-Lin,Luo, Wei-Ping,Liu, Qiang,Guo, Can-Cheng
, p. 13446 - 13453 (2021/10/12)
Two C=C bond participation in annulation to pyridines using N,N-dimethylformamide (DMF) as the N1 and C4 synthons has been carried out. In this reaction, DMF contributed one N atom and one C atom to two disconnected positions of pyridine ring, with no need for an additional nitrogen source. Two C=C bonds in two molecules of substituted styrenes offered four carbon atoms in the presence of iodine and persulfate. With the optimized conditions in hand, both symmetric and unsymmetric diaryl-substituted pyridines were obtained in useful yields. On the basis of relevant literature and a series of control experimental results, a possible mechanism was proposed in this work, which may demonstrate how DMF provides both N1 and C4 sources.
Method for constructing 3,5-disubstituted pyridine from aryl ethylene and N,N-dimethylformamide through cyclization reaction
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Paragraph 0089; 0090; 0091; 0092; 0093, (2020/09/09)
The invention discloses a method for constructing 3,5-disubstituted pyridine from aryl ethylene and N,N-dimethylformamide through a cyclization reaction. The method comprises carrying out cyclizationon the aryl ethylene, the N,N-dimethylformamide and peroxydisulfate under the catalytic action of iodized salt to obtain the 3,5-disubstituted pyridine. According to the method, iodine salt is utilized to catalyze one-step oxidative cyclization of the aryl ethylene and DMF to synthesize 3,5-disubstituted pyridine, and the method has the advantages of low cost of raw materials and catalysts, mild reaction conditions, capability of obtaining symmetric 3,5-disubstituted pyridine with high selectivity and high yield and the like.
Method for constructing 3,5-disubstituted pyridine by utilizing mixed styrene derivative and N,N-dimethylformamide
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Paragraph 0101-0107, (2020/08/27)
The invention discloses a method for constructing 3,5-disubstituted pyridine by utilizing mixed styrene derivative and N,N-dimethylformamide. The method comprises the following step: subjecting the mixed styrene derivative, N,N-dimethylformamide and peroxydisulfate to a cyclization reaction under the catalytic action of iodized salt so as to obtain symmetrical and asymmetrical mixed 3,5-disubstituted pyridine products at the same time. According to the method, 3,5-disubstituted pyridine is synthesized from the mixed styrene derivative and DMF through one-step oxidative cyclization under the catalysis of iodate; and the method has the advantages of low raw material and catalyst cost, mild reaction conditions, capability of realizing high-yield preparation of the symmetrical and asymmetrical3,5-disubstituted pyridine products at the same time and the like.
Cu-Catalyzed concise synthesis of pyridines and 2-(1 H)-pyridones from acetaldehydes and simple nitrogen donors
Li, Ziyuan,Huang, Xiaoqiang,Chen, Feng,Zhang, Chun,Wang, Xiaoyang,Jiao, Ning
supporting information, p. 584 - 587 (2015/03/04)
A highly selective copper-catalyzed concise synthesis of 3,5-diarylpyridine and 2-(1H)-pyridone has been achieved through cascade Chichibabin-type cyclization, C(sp3)-C(sp3) cleavage, and aerobic oxidation. Azide, ceric ammonium nitrate (CAN), and 2-aminopyridine are disclosed as efficient nitrogen donors in this Cu-catalysis using O2 as the oxidant. Water and molecular oxygen were employed as the oxygen source in the case of oxygenation.
Metal-free synthesis of substituted pyridines from aldehydes and NH4OAc under air
Yan, Rulong,Zhou, Xiaoqiang,Li, Ming,Li, Xiaoni,Kang, Xing,Liu, Xingxing,Huo, Xing,Huang, Guosheng
, p. 50369 - 50372 (2014/12/10)
A metal-free and efficient method for the synthesis of substituted pyridines with aldehydes and NH4OAc under mild conditions using air as the oxidant was developed. This oxidative cyclization process involves direct C-H bond functionalization, C-C/C-N bond formation and C-C bond cleavage.
Suzuki coupling of heteroaromatic chlorides using highly electron-donating clickphos ligands
Spinella, Stephen M.,Guan, Zheng-Hui,Chen, Jian,Zhang, Xumu
experimental part, p. 3094 - 3098 (2009/12/28)
Using highly electron-rich monophosphine ligands, Suzuki cross-coupling of heteroaromatic chlorides with various boronic acids was carried out in high yields. High yields were also often observed when steric heteroaromatic chlorides were employed in Suzuki cross-coupling reactions.
