634-35-5Relevant articles and documents
Iodination/Amidation of the N-Alkyl (Iso)quinolinium Salts
Tang, Juan,Chen, Xue,Zhao, Chao-Qun,Li, Wen-Jing,Li, Shun,Zheng, Xue-Li,Yuan, Mao-Lin,Fu, Hai-Yan,Li, Rui-Xiang,Chen, Hua
supporting information, p. 716 - 730 (2020/12/22)
The NaIO4-mediated sequential iodination/amidation reaction of N-alkyl quinolinium iodide salts has been first developed. This cascade process provides an efficient way to rapidly synthesize 3-iodo-N-alkyl quinolinones with high regioselectivity and good functional group tolerance. This protocol was also amenable to the isoquinolinium salts, thus providing a complementary method for preparing the 4-iodo-N-alkyl isoquinolinones.
External Heavy-Atom Effect via Orbital Interactions Revealed by Single-Crystal X-ray Diffraction
Sun, Xingxing,Zhang, Baicheng,Li, Xinyang,Trindle, Carl O.,Zhang, Guoqing
, p. 5791 - 5797 (2016/08/05)
Enhanced spin-orbit coupling through external heavy-atom effect (EHE) has been routinely used to induce room-temperature phosphorescence (RTP) for purely organic molecular materials. Therefore, understanding the nature of EHE, i.e., the specific orbital interactions between the external heavy atom and the luminophore, is of essential importance in molecular design. For organic systems, halogens (e.g., Cl, Br, and I) are the most commonly seen heavy atoms serving to realize the EHE-related RTP. In this report, we conduct an investigation on how heavy-atom perturbers and aromatic luminophores interact on the basis of data obtained from crystallography. We synthesized two classes of molecular systems including N-haloalkyl-substituted carbazoles and quinolinium halides, where the luminescent molecules are considered as "base" or "acid" relative to the heavy-atom perturbers, respectively. We propose that electron donation from a π molecular orbital (MO) of the carbazole to the σ? MO of the C-X bond (π/σ?) and n electron donation to a π? MO of the quinolinium moiety (n/π ?) are responsible for the EHE (RTP) in the solid state, respectively.
Solvent-free 1H-tetrazole, 1,2,5,6-tetrahydronicotinonitrile and pyrazole synthesis using quinoline based ionic fluoride salts (QuFs): thermal and theoretical studies
Iqbal, Nafees,Hashim, Jamshed,Ali, Syed Abid,Al-Rashida, Mariya,Alharthy, Rima D.,Ahmad, Shakeel,Khan, Khalid Mohammed,Basha, Fatima Zahra,Moin, Syed Tarique,Hameed, Abdul
, p. 95061 - 95072 (2015/11/17)
The role of ionic liquids as catalyst and solvent to mediate organic reactions is well documented. While imidazole and pyridine-based ionic liquids have traditionally been the ionic liquids of choice for organic synthesis, imidazole's inert nature and pyridine's toxicity are often viewed as impediments. In the present study, we have synthesized ionic liquids (QuFs), employing the non-toxic quinoline ring. The desired QuFs were readily prepared via N-alkylation and corresponding anion exchange with fluoride ions. The structures of the synthesized QuFs were confirmed with advanced spectroscopic techniques such as 1H and 13C NMR, IR and mass spectrometry. The potential of these newly synthesized QuFs as catalyst for click chemistry and other reactions was explored by carrying out synthesis of 5-(p-methylphenyl)-1H-tetrazole (7), 2-dicyanomethylene-6-methyl-4,6-bis(m-methoxyphenyl)-1,2,5,6-tetrahydronicotinonitrile (12), and 3,5-dimethyl-1-(p-methoxy)-1H-pyrazole (15). Detailed thermal analysis (DSC, TGA and DTG) was carried out to study the thermal stability of synthesized QuFs. Density functional theory (DFT) calculations and molecular dynamics simulations were also carried in order to establish a relationship between binding energies, and structural and dynamic characteristics of QuFs.
