15366-86-6Relevant 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
-
Paragraph 0144; 0145; 0146; 0147; 014813, (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.
Insight into Copper Catalysis: In Situ Formed Nano Cu2O in Suzuki-Miyaura Cross-Coupling of Aryl/Indolyl Boronates
Ranjani, Ganapathy,Nagarajan, Rajagopal
, p. 3974 - 3977 (2017/08/14)
A ligand-free copper catalyzed Suzuki-Miyaura coupling of 3,5-diiodopyridine with aryl and indole boronates has been explored in good to excellent yields. In situ generation of nano-Cu2O from CuCl2 under the reaction conditions has been discovered for the first time. The generality of the reaction was further demonstrated by the arylation of 5-iodopyrimidine, iodopyridines, iodobenzenes, and diiodobenzenes and resulted in good to moderate yields. Moreover, bisindole alkaloid Scalaridine A has been successfully synthesized in 60% overall yield.
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.
Triarylbismuthanes as threefold aryl-transfer reagents in regioselective cross-coupling reactions with bromopyridines and quinolines
Rao, Maddali L.N.,Dhanorkar, Ritesh J.
supporting information, p. 5214 - 5228 (2014/10/15)
Cross-coupling studies using bromopyridines and bromoquinolines with triarylbismuths as threefold coupling reagents in substoichiometric amounts under Pd-catalysed conditions are disclosed. The reactivity was high with both mono- and dibromopyridyl substrates, and mono- and bis-couplings were carried out regioselectively. A library of monoaryl and diaryl pyridines was formed in high yields. A one-pot strategy provided a simple and straightforward synthesis of both symmetrical and unsymmetrical diarylpyridines. Arylations of 2-bromo- and 3-bromoquinolines were achieved with triarylbismuth reagents. This study demonstrates that triarylbismuths may be used as threefold arylating reagents for the synthesis of aryl pyridines and quinolines through couplings with bromopyridines and bromoquinolines under Pd-catalysed conditions. Copyright
Use of the curtius rearrangement of acryloyl azides in the synthesis of 3,5-disubstituted pyridines: Mechanistic studies
Chuang, Ta-Hsien,Chen, Yu-Chi,Pola, Someshwar
experimental part, p. 6625 - 6630 (2010/11/18)
A series of disubstituted pyridine derivatives was synthesized from the corresponding acryloyl azides by acetic acid-promoted cycloaddition. This represents a novel and convenient synthetic approach to the symmetric 3,5-disubstituted pyridines. The nature of the substituent on the double bond and the utilized solvent were found to be crucial to the yield of pyridines. The reactivity of the acid-promoted cycloaddition increases with the presence of aryl groups, such as phenyl and pyridinyl. We also explored the comprehensive mechanism by the acid-promoted cycloaddition of 13C-labeled cinnamoyl azide. The symmetric 3,5-disubstituted pyridines were synthesized from acryloyl azides by acetic acid-promoted trimolecular condensation.
Total synthesis of haouamine A: the indeno-tetrahydropyridine core
Burns, Noah Z.,Jessing, Mikkel,Baran, Phil S.
scheme or table, p. 6600 - 6610 (2011/02/25)
A full account of synthetic efforts toward the indeno-tetrahydropyridine core of haouamine A is presented. Initial failed strategies led to the unexpected discovery of a mild abnormal Chichibabin pyridine synthesis and provided knowledge and inspiration f
Synthesis of 2,5- and 3,5-diphenylpyridine derivatives for DNA recognition and cytotoxicity
Jacquemard, Ulrich,Routier, Sylvain,Dias, Nathalie,Lansiaux, Amelie,Goossens, Jean-Francois,Bailly, Christian,Merour, Jean-Yves
, p. 1087 - 1095 (2007/10/03)
A series of 2,5- and 3,5-diphenylpyridine derivatives was synthetised in high yields. A versatile chemical strategy allows the design of diphenylpyridines differently substituted with cationic or neutral side chains. The interaction of the molecules with
