1,2,3,4-Tetrahydroquinoxaline

General procedure: N-Heterocyclic amine (0.50 mmol), CoTPP (10 mg) and DMF (2 mL) were mixed in a carousel reaction tube. The reaction mixture was stirred at 120 C under oxygen atmosphere, the reaction was sampled periodically and monitored by TLC (petroleum ether/ethyl acetate (10:1 v/v)). After the reaction, the reaction mixture was then cooled to room temperature and purified using flash chromatography to give the corresponding product. All the dehydrogenation products are known, and their NMR spectra were consistent with the literature. NMR spectra were recorded at 25 C on an Bruker AVANCE III 400-NMR spectrometer at 400 MHz for 1H and 100 MHz for 13C, using CDCl3 as solvent with TMS as the internal standard. Thin-layer chromatography was performed on silica gel 60 F254 (Sinopharm) thin-layer chromatography plates using petroleum ether/ethyl acetate (10:1 v/v) as the mobile phase.General procedure: To a Schlenk tube equipped with a magnetic stir bar were added8-methyl-1, 2, 3, 4-tetrohydroquinoline (0.50 mmol), FeCl2 (1.9mg, 1.5·10-2 mmol), DMSO (31.2 mg, 0.4 mmol), and p-xylene (1mL). The reaction mixture was stirred at 110 C under anoxygen atmosphere using a balloon and monitored by TLC. Afterthe reaction, the mixture was cooled to room temperature andpurified using flash chromatography (hexane-EtOAc, 10:1) togive the corresponding product 8-methylquinoline in 70% yield.8-MethylquinolineColorless oil. 1H NMR (400 MHz, CDCl3): delta = 8.93 (m, 1 H), 8.10(m, 1 H), 7.64 (d, J = 4.0 Hz, 1 H), 7.54 (m, 1 H), 7.43-7.35 (m, 2H) 2.82 (s, 3 H). 13C NMR (100 MHz, CDCl3): delta = 149.2, 147.3, 137.1, 136.3, 129.6, 128.3, 126.3, 125.9, 120.8, 18.2. HRMS: m/zcalcd for [C10H9N + H+]: 144.0813; found: 144.0813.General procedure: 200mg Ni2Mn-LDH type hydrotalcite catalyst, 0.5mmol tetrahydroquinoline and 2mL 1, 3, 5-trimethylbenzene solvent Was added to the reactor, the reaction was carried out at atmospheric pressure and at a temperature of 80 C. The reaction time was 2.5 h under an atmosphere of oxygen, and the contents of the quinoline, the starting material, in the liquid were analyzed by gas chromatography internal standard method (nitrobenzene as internal standard) Content, The conversion and selectivity of the reaction were calculated. The conversion of tetrahydroquinoline was> 99% and the selectivity of the reaction was 78.3%

Molecular Weight:134.18
XLogP3:1.7
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:2
Exact Mass:134.084398327
Monoisotopic Mass:134.084398327
Topological Polar Surface Area:24.1
Heavy Atom Count:10
Complexity:99.8
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes