168426-25-3Relevant articles and documents
Highly efficient one pot palladium-catalyzed synthesis of 3,5-bis (arylated) pyridines: Comparative experimental and DFT studies
Adeel, Muhammad,Akram, Muhammad,Aliabad, Hossein Asghar Rahnamaye,Braga, Ataualpa A. C.,Iqbal, Javed,Khalid, Muhammad,Tahir, Muhammad Nawaz,Ullah, Malik Aman
, (2020)
Many different alkyl and aryl substituted pyridine based organic derivatives have been synthesized due to its uniqueness pyridine core. However, the transition metal catalyzed Suzuki cross coupling reaction has provided an easy route to the synthesis of a
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 0134; 0135; 0136; 0137; 0138, (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.
Molecular Iodine-Mediated Chemoselective Synthesis of Multisubstituted Pyridines through Catabolism and Reconstruction Behavior of Natural Amino Acids
Xiang, Jia-Chen,Wang, Miao,Cheng, Yan,Wu, An-Xin
supporting information, p. 24 - 27 (2016/01/15)
A new process has been developed for the selective construction of 2,6-disubstituted, 2,4,6-trisubstituted, and 3,5-disubstituted pyridines based on the catabolism and reconstruction behaviors of amino acids. Molecular iodine was used as a tandem catalyst to trigger the decarboxylation-deamination of amino acids and to promote the subsequent formation of the pyridine products.
Synthesis of dicationic diarylpyridines as nucleic-acid binding agents
Kumar,Rhodes,Spychala,Wilson,Boykin,Tidwell,Dykstra,Hall,Jones,Schinazi
, p. 99 - 106 (2007/10/02)
The syntheses of 2,6-bis[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl]pyridine 7, 2-[4-(4,5-dihydro-1H-imidazol-2-yl)-phenyl]-6-[3-(4,5-dihydro- 1H-imidazol-2-yl)phenyl]pyridine 8 and 2,6-bis[3-(4,5-dihydro-1H-imidazol-2-yl)phenyl]pyridine 9 in five steps from the appropriately substituted bromoacetophenone are described. 3,5-Bis[4-(4,5-dihydro-1H-imidazol-2-yl) phenyl]pyridine 13 is also reported, prepared in four steps from 4-bromophenylacetonitrile. The preparation of 2,5-bis[4-(4,5-dihydro-IH-imidazol-2-yl) phenyl]pyridine Is from 4-bromoacetophenone in six steps is presented. The dications bind to poly dA·dT in the order 7 > 13 > 18 > 8 > 9; the order of binding to poly A·U is 7 > 13 > 8 > 9; 18 essentially does not bind to the RNA model. Only 7 inhibits topoisomerase II at millimolar concentrations. The dicationic compounds that were tested against Pneumonocystis carinii in the immunosuppressed rat model show only modest activity and are moderately toxic. Some of the compounds demonstrated modest anti-HIV-1 activity and selectivity in primary lymphocytes.
