Microwave-assisted simple synthesis of quinolines from anilines and alkyl vinyl ketones on the surface of silica gel in the presence of indium(III) chloride

Tetrahedron Letters

Volumn 41, Issue 4, 2000, Pages 531-533

  Ranu, Brindaban C ^a   Hajra, Alakananda ^a   Jana, Umasish ^a  

^a DEPARTMENT OF MATERIALS SCIENCE   (India)

Author keywords

Chloride; Indium(III); Microwave heating; Quinolines; Silica gel

Indexed keywords

ANILINE DERIVATIVE; INDIUM CHLORIDE IN 111; KETONE DERIVATIVE; QUINOLINE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; MICROWAVE IRRADIATION; REACTION ANALYSIS; SYNTHESIS;

EID: 0034700808     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)02111-5     Document Type: Article

References (17)

1. (a) Morimoto, Y.; Matsuda, F.; Shirahama, H. Synlett 1991, 202.
2. (b) Isobe, M.; Nishikawa, T.; Yamamoto, N.; Tsukiyama, T.; Ino, A.; Okita, T. J. Heterocycl. Chem. 1992, 29, 619.
3. (c) Michael, J. P. Nat. Prod. Rep. 1997, 14, 605, and references cited therein.
4. (a) Markees, D. G.; Dewey, V. C.; Kidder, G. W. J. Med. Chem. 1970, 13, 324.
5. (b) Alhaider, A. A.; Abdelkader, M. A.; Lien, E. J. J. Med. Chem. 1985, 28, 1398.
6. (c) Campbell, S. F.; Hardstone, J. D.; Palmer, M. J. J. Med. Chem. 1988, 31, 1031.
7. Manske, R. H. F.; Kulka, M. In Organic Reactions; Adams, R., Ed.; Wiley: New York, 1953; Vol. 7, p. 59.
8. (a) Cho, C. S.; Oh, B. H.; Shim, S. C. Tetrahedron Lett. 1999, 40, 1499.
9. (b) Zhou, L.; Zhang, Y. J. Chem. Soc., Perkin Trans. 1 1998, 2899.
10. (c) Larock, R. C.; Kero, M.-Y. Tetrahedron Lett. 1991, 32, 569.
11. (d) Zhou, L.; Tu, S.; Shi, D.; Dai, G.; Chen, W. Synthesis 1988, 851.
12. (e) Larock, R. C.; Babu, S. Tetrahedron Lett. 1987, 28, 5291.
13. (f) Ozawa, F.; Yanagihara, H.; Yamamoto, A. J. Org. Chem. 1986, 51, 415.
14. (g) Tsuji, Y.; Hu, K.-T.; Watanabe, Y. J. Org. Chem. 1987, 52, 1673, and references cited therein.
15. 3 (0.3 mmol) in THF (1 ml) followed by complete evaporation of solvent under reduced pressure.
16. Loh, T.-P.; Wei, L.-L. Synlett 1998, 975.
17. 3. This type of oxidative aromatization in the presence of Lewis acid and air is well documented in the literature: Ogata, Y.; Kawaski, A.; Suyama, S. Tetrahedron 1969, 25, 1369.