Dehydrogenation of 1,2,3,4-tetrahydroquinoline and its related compounds: Comparison of Pd/C-ethylene system and activated carbon-O2 system

Tetrahedron Letters

Volumn 51, Issue 35, 2010, Pages 4633-4635

  Tanaka, Takanori ^a   Okunaga, Ken Ichi ^a   Hayashi, Masahiko ^a  

^a KOBE UNIVERSITY   (Japan)

Author keywords

Activated carbon; Heteroaromatic compounds; Oxidation

Indexed keywords

1,2,3,4 TETRAHYDROCARBAZOLE DERIVATIVE; 1,2,3,4 TETRAHYDROQUINOLINE DERIVATIVE; ACTIVATED CARBON; AROMATIC COMPOUND; ETHYLENE; OXYGEN; PALLADIUM; TETRAHYDROISOQUINOLINE DERIVATIVE;

AROMATIZATION; ARTICLE; COMPARATIVE STUDY; DEHYDROGENATION; OXIDATION; QUANTUM YIELD; REACTION ANALYSIS;

EID: 77955654724     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.06.118     Document Type: Article

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14. 3): δ 8.92 (d, J = 4.0 Hz, 1H), 8.15 (d, J = 8.0 Hz, 1H), 8.11 (d, J = 8.8 Hz, 1H), 7.82 (d, J = 7.6 Hz, 1H), 7.73 (t, J = 7.2 Hz, 1H), 7.56 (d, J = 7.2 Hz, 1H), 7.40 (dd, J = 4.4, 4.4 Hz, 1H).
15. 2 system: Synthesis of quinoline (7). A mixture of 1,2,3,4-tetrahydroquinoline (133.2 mg, 1 mmol), 100 wt % of activated carbon (Charcoal Activated, TOKYO CHEMICAL INDUSTRY CO., LTD (TCI)), and anhydrous xylene (5 mL) was placed in a three-necked flask under an oxygen atmosphere using a balloon. The whole was heated to 120°C and stirred for 24 h at this temperature. After confirmation of the completion of the reaction by TLC analysis (hexane/ethyl acetate = 1:2), activated carbon was filtered off using Celite. After washing with ethyl acetate, the filtrate was evaporated and the resulting liquid was purified by silica gel column chromatography. Quinoline was obtained in 111.1 mg (86% yield).
16. 3): δ 9.20 (s, 1H), 8.52 (d, J = 6.0 Hz, 1H), 7.96 (d, J = 8.4 Hz, 1H), 7.81 (d, J = 8.4 Hz, 1H), 7.7-7.6 (m, 3H).
17. 3): δ 11.3 (br s, 1H), 8.10 (d, J = 7.6 Hz, 2H), 7.47 (d, J = 8.0 Hz, 2H), 7.38 (t, J = 8.0 Hz, 2H), 7.15 (t, J = 7.6 Hz, 1H).
18. 1H NMR spectra were identified with authentic compounds.
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