Contents General Information General procedure for the dehydrogenation of N-heterocyclic amines Spectrometric data of the products References General Information All the chemicals were purchased from Aldrich or Alfa. Unless otherwise specified, reagents and solvents were used as received. Substituted 1,2,3,4-tetrohydroquinolines were prepared by the reduction of corresponding quinolines according to the literature method using NaBH 4 as the reductant, 1 and 1,2,3,4-tetrahydroquinoxaline derivatives were also obtained from the corresponding quinoxalines by the same method. 3-Methyl-1,2,3,4tetrahydrobenzo[f]quinoline was prepared according to the literature method using triethylamine/formic acid azeotrope as the hydrogen source. 2 Melting points were measured on a Gallenkamp melting point apparatus. NMR spectra were recorded at 25 ℃ on an Bruker 400-NMR spectrometer at 400 MHz for 1 H and 100 MHz for 13 C, using CDCl 3 as solvent with TMS as the internal standard. High-resolution mass spectra were obtained by means of a Agilent QTOF 7200 instrument. Thin-layer chromatography was performed on silica gel 60 F254 (Merck) thin-layer chromatography plates using hexane/ethyl acetate (10:1 v/v) as the mobile phase. General procedure for the dehydrogenation of N-heterocyclic amines N-Heterocyclic amine (0.50 mmol), FeCl 2 (1.9 mg, 1.5x10-2 mmol) and DMSO (31.2 mg, 0.4 mmol) were dissolved in p-xylene (1 mL) in a carousel reaction tube. The reaction mixture was stirred at 110 ℃ under an oxygen atmosphere using a balloon and monitored by TLC. After the reaction, the mixture was 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.
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