373647-96-2Relevant academic research and scientific papers
Fluorine-containing pyridine imine ligand, transition metal complex thereof and application of ligand to polyisoprene synthesis
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Paragraph 0060; 0068; 0069; 0070, (2018/11/03)
The invention discloses a fluorine-containing pyridine imine ligand, a transition metal complex thereof and an application of the ligand to polyisoprene synthesis, and belongs to the field of new compounds and metal organic synthesis. The complex is used
Diverse C-6 substituted 4-methyl-2-(2-, 3- and 4-pyridinyl)quinolines: synthesis, in vitro anticancer evaluation and in silico studies
Kouznetsov, Vladimir V.,Robles-Castellanos, Mayra L.,Sojo, Felipe,Rojas-Ruiz, Fernando A.,Arvelo, Francisco
, p. 551 - 561 (2017/02/15)
A series of twelve 4-methyl-2-(2-, 3- and 4-pyridinyl)quinolines 7–9 was synthesized using modified Kametani reaction protocol and their in vitro cytotoxicity was tested against human cancer cell lines MCF-7, SKBR-3, PC3, HeLa, comparing with human dermis
Quantitative Reactivity Scales for Dynamic Covalent and Systems Chemistry
Zhou, Yuntao,Li, Lijie,Ye, Hebo,Zhang, Ling,You, Lei
supporting information, p. 381 - 389 (2016/01/26)
Dynamic covalent chemistry (DCC) has become a powerful tool for the creation of molecular assemblies and complex systems in chemistry and materials science. Herein we developed for the first time quantitative reactivity scales capable of correlation and prediction of the equilibrium of dynamic covalent reactions (DCRs). The reference reactions are based upon universal DCRs between imines, one of the most utilized structural motifs in DCC, and a series of O-, N-, and S- mononucleophiles. Aromatic imines derived from pyridine-2-carboxyaldehyde exhibit capability for controlling the equilibrium through distinct substituent effects. Electron-donating groups (EDGs) stabilize the imine through quinoidal resonance, while electron-withdrawing groups (EWGs) stabilize the adduct by enhancing intramolecular hydrogen bonding, resulting in curvature in Hammett analysis. Notably, unique nonlinearity induced by both EDGs and EWGs emerged in Hammett plot when cyclic secondary amines were used. This is the first time such a behavior is observed in a thermodynamically controlled system, to the best of our knowledge. Unified quantitative reactivity scales were proposed for DCC and defined by the correlation log K = SN (RN + RE). Nucleophilicity parameters (RN and SN) and electrophilicity parameters (RE) were then developed from DCRs discovered. Furthermore, the predictive power of those parameters was verified by successful correlation of other DCRs, validating our reactivity scales as a general and useful tool for the evaluation and modeling of DCRs. The reactivity parameters proposed here should be complementary to well-established kinetics based parameters and find applications in many aspects, such as DCR discovery, bioconjugation, and catalysis.
Studies of electronic effects of modified pyridine-imine ligands utilized in cobalt-catalyzed meta-selective Diels-Alder reactions
Hilt, Gerhard,Janikowski, Judith,Schwarzer, Martin,Burghaus, Olaf,Sakow, Dimitri,Br?ring, Martin,Drüschler, Marcel,Huber, Benedikt,Roling, Bernhard,Harms, Klaus,Frenking, Gernot
, p. 219 - 223 (2013/11/06)
The regioselectivity of cobalt-catalyzed Diels-Alder reactions can be controlled by the choice of ligands on the cobalt center. Ligands of the pyridine-imine type favor the formation of the 1,3-disubstitution pattern on the dihydroaromatic product. The investigation was aimed to elucidate the factors for controlling the regioselectivities and reactivity induced by electronic effects of the pyridine-imine ligands in the cobalt-catalyzed Diels-Alder reaction. For that, electron-withdrawing as well as electron donating substituents were introduced in the 4-position on the pyridine moiety and on the 4′-position of the aniline derivative used in the imine subunit of the ligands. In close synergy DFT calculations and the comparison with experimental results proved that electronic variation of the substituents at both positions have a negligible influence on the regioselectivity. However, the kinetic data for the cobalt-catalyzed Diels-Alder reactions revealed that there are great differences in the lengths of the induction periods when different cobalt pyridine-imine complexes are applied. These results could be elucidated by conductivity experiments showing that ionic homoleptic complexes Co(L) 22+/CoBr42- are in equilibrium with their corresponding neutral heteroleptic complexes of type Co(L)Br2 in solution. The equilibrium position depends on the electronic characteristics of the pyridine-imine ligands (L), thereby influencing the length of the induction period.
Multicomponent reaction of imidazo[1,5- a ]pyridine carbenes with aldehydes and dimethyl acetylenedicarboxylate or allenoates: A straightforward approach to fully substituted furans
Pan, Huan-Rui,Li, Yong-Jia,Yan, Cai-Xia,Xing, Juan,Cheng, Ying
supporting information; experimental part, p. 6644 - 6652 (2010/11/17)
The facile three-component reactions of N,N-substituted imidazo[1,5-a]pyridine carbenes, namely imidazo[1,5-a]pyridin-3-ylidenes, with aldehydes and DMAD or allenoates were disclosed. Both reactions proceeded via tandem nucleophilic addition, [3 + 2]-cycloaddition, and ring transformation to produce different 4-[(2-pyridyl)methyl]aminofuran derivatives generally in moderate yields. This work not only 'rovided the first example of the application of imidazo[1,5-a]pyridin-3-ylidenes in organic synthesis but also developed a straightforward approach to fully substituted furans that are not easily accessible by other methods.
