529-81-7Relevant articles and documents
An unusual synthesis of Troeger's bases using DMSO/HCl as formaldehyde equivalent
Li, Zhong,Xu, Xiaoyong,Peng, Yanqing,Jiang, Zhaoxing,Ding, Chuanyong,Qian, Xuhong
, p. 1228 - 1230 (2005)
The reactions between anilines and DMSO/HCl produce Troeger's bases in moderate yield. The Troeger's bases bearing an electron-withdrawing group can also be synthesized through this procedure. In this reaction, DMSO/HCl acts as formaldehyde equivalent. Ge
The mechanism of Troeger's base formation probed by electrospray ionization mass spectrometry
Abella, Carlos A. M.,Benassi, Mario,Santos, Leonardo S.,Eberlin, Marcos N.,Coelho, Fernando
, p. 4048 - 4054 (2007)
(Chemical Equation Presented) Using direct infusion electrospray ionization mass and tandem mass spectrometric experiments [ESI-MS(/MS)], we have performed on-line monitoring of some reactions used to form Troeger's bases. Key intermediates, either as cationic species or as protonated forms of neutral species, have been intercepted and characterized. The role of urotropine as the methylene source in these reactions has also been accessed. Reaction pathways shown by ESI-MS(/MS) have been probed by gas-phase ion/molecule reactions, and an expanded mechanism for Troeger's base formation based on the mass spectrometric data has been elaborated.
Design and synthesis of a novel banana-shaped functional molecule via double cross-coupling
Yang, Bingchuan,Shen, Guodong,Huang, Xianqiang,Liu, Rutao
, (2019)
A novel banana-shaped molecule using 2,8-Dimethyl-6H,12H-5,11-methanodibenzo [b,f] [1,5]diazocine (Tr?ger’s base) as bent-core was synthesized via double Carbon-Carbon cross-coupling reaction. The double Sonogashira cross-coupling reaction was optimized by using Pd(PPh3)2Cl2 as catalyst, CuI as cocatalyst and diisopropylamine as base in place of triethylamine. The structure of this compound was confirmed by 1H-NMR, 13C-NMR, Fourier transform infrared (FT-IR) spectroscopy and mass spectrometry.
Synthesis of new cyano-substituted analogues of Tr?ger's bases from bromo-derivatives. A stereochemical dependence of long-range (nJHH, n?=?4, 5, and 6) proton–proton and proton–carbon (nJCH, n?=?1, 2, 3, 4, and 5) coupling constants of these compounds
Dusso, Diego,Ramirez, Cristina,Parise, Alejandro,Lanza,Vera, D. Mariano,Chesta, Carlos,Moyano, E. Laura,Akhmedov, Novruz G.
, p. 423 - 454 (2019/05/24)
A free-catalyst microwave-assisted cyanation of brominated Tr?ger's base derivatives (2a-f) is reported. The procedure is simple, efficient, and clean affording the nitrile compounds (3a-e, I) in very good yields. Complete assignment of 1H and 13C chemical shifts of 2a-f, I and 3a-d, I was achieved using gradient selected 1D nuclear magnetic resonance (NMR) techniques (1D zTOCSY, PSYCHE, DPFGSE NOE, and DEPT), homonuclear 2D NMR techniques (gCOSY and zTOCSY), and heteronuclear 2D NMR techniques (gHSQCAD/or pure-shift gHSQCAD, gHMBCAD, bsHSQCNOESY, and gHSQCAD-TOCSY) with adiabatic pulses. Determination of the long-range proton–proton coupling constants nJHH (n?=?4, 5, 6) was accomplished by simultaneous irradiation of two protons at appropriate power levels. In turn, determined coupling constants were tested by an iterative simulation program by calculating the 1H NMR spectrum and comparing it to the experimental spectrum. The excitation-sculptured indirect-detection experiment (EXSIDE) and 1H-15N CIGARAD-HMBC (constant time inverse-detection gradient accordion rescaled heteronuclear multiple bond correlation) were applied for determination of long-range carbon–proton coupling constants nJCH (n?=?2, 3, and 4) and for assignment of 15N chemical shift at natural abundance, respectively. DFT/B3LYP optimization studies were performed in order to determine the geometry of 2c using 6-31G(d,p), 6-311G(d,p), and 6–311?+?G(d,p) basis sets. For calculation of 1H and 13C chemical shifts, nJHH (n?=?2, 3, 4, 5, and 6), and nJCH (n?=?1, 2, 3, and 4) coupling constants, the GIAO method was employed at the B3LYP/6-31G(d,p), B3LYP/6-31+G(d,p), B3LYP/6-311+G(d,p), B3LYP/6-311++G(2d,2p), B3LYP/cc-pVTZ), and B3LYP/aug-cc-pVTZ) levels of theory. For the first time, a stereochemical dependence magnitude of the long-range nJHH (n?=?4, 5, and 6) and nJCH (n?=?1, 2, 3, 4, and 5) have been found in bromo-substituted analogues of Tr?ger's bases.
Synthesis of quinolines from anilines, acetophenones and DMSO under air
Jiang, Tao-Shan,Wang, Xi,Zhang, Xiuli
, p. 2979 - 2982 (2018/06/29)
An efficient CH3SO3H-promoted synthesis of quinolines from readily available anilines, acetophenones and DMSO under air is reported. This protocol gives diverse substituted 4-arylquinolines in moderate to high yields with broad substrate/functional group tolerance. Preliminary mechanistic studies demonstrate that DMSO may be transformed to HCHO in this process and used as a one carbon source.
