FeCl3-NaI mediated reactions of aryl azides with 3,4-dihydro-2H-pyran: A convenient synthesis of pyranoquinolines

Tetrahedron Letters

Volumn 45, Issue 17, 2004, Pages 3507-3509

  Kamal, Ahmed ^a   Prasad, B Rajendra ^a   Ramana, A Venkata ^a   Babu, A Hari ^a   Reddy, K Srinivasa ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

Aryl azide; Ferric chloride; Pyranoquinolines; Reductive cyclization; Sodium iodide

Indexed keywords

3,4 DIHYDRO 2H PYRAN; AZIDE; FERRIC CHLORIDE; PYRAN DERIVATIVE; QUINOLINE DERIVATIVE; SODIUM IODIDE; TETRAHYDROQUINOLINE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CYCLIZATION;

EID: 1842788567     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.02.146     Document Type: Article

References (37)

1. (a) Ramesh M., Moham P.S., Shanmugam P. Tetrahedron. 40:1984;4041.
2. (b) Witherup, K. M.; Ransom, R. W.; Varga, S. L; Pitzenberger, S. M.; Lotti, V. J; Lumma, W. J. U.S. Patent US 5288725, 1994; Chem. Abstr. 1994, 121, 91779s
3. (c) Perry N.B., Blunt J.W., McCombs J.D., Munro M.H.G. J. Org. Chem. 51:1986;5476.
4. (d) Williamson N.M., March P.R., Ward A.D. Tetrahedron Lett. 36:1995;7721.
5. (e) Johnson J.V., Eauckman S., Baccanari P.D., Roth B. J. Med. Chem. 32:1989;1942.
6. (f) Biller, S. A.; Misra, R. N. U.S. Patent US 4843082, 1989; Chem. Abstr. 1989, 111, 232600j.
7. (g) Celing R.W., Leeson P.D., Moseley A.M., Baker R., Foster A.C., Grimwood S., Kemp J.A., Marshall G.R. J. Med. Chem. 35:1992;1942.
8. (h)Carling R.W., Leeson P.D., Moseley A.M., Smith J.D., Saywell K., Trickelbank M.D., Kemp J.A., Marshall G.R., Foster A.C., Grimwood S. Bioorg. Med. Chem. Lett. 3:1993;65.
9. (i) Cuny, G. D.; Hauske, J. D.; Hoemann, M. Z.; Rossi, R. F.; Xie, R. L. PCT Int. Appl. 1999, WO 9967238
10. Chem. Abstr. 132:1999;64182.
11. (j) Hanada, K.; Furuya, K.; Inoguchi, K.; Miyakawa, M.; Nagata, N. PCT Int. Appl. 2001, WO 0127086
12. Chem. Abstr. 134:2001;295752.
13. Mohamed E.A. Chem. Pap. 48:1994;261.
14. Chem. Abstr. 123:1995;9315.
15. Katritzky A.R., Rachwal S., Rachwal B. Tetrahedron. 12:1996;15031.
16. Povarov L.S. Russ. Chem. Rev. Engl. Transl. 36:1967;656.
17. Boger D.L., Weinreb S.M. Hetero Diels-Alder Methodology in Organic Synthesis. 1987;Academic, San Diego. Chapters 2 and 9.
18. (a) Crousse B., Begue J., Bonnet-Delpon D. J. Org. Chem. 65:2000;5009.
19. (b) Mendoza, J. S. PCT Int. Appl. 1998, WO 9827093
20. Chem. Abstr. 129:1998;95393.
21. (c) Makioka Y., Shindo T., Taniguchi Y., Takaki K., Fujiwara Y. Synthesis. 1995;801.
22. (d) Lucchini V., Prato M., Scorrano G., Stivanello M., Valle G. J. Chem. Soc., Perkin Trans. 2. 1992;259.
23. (e) Kametani T., Furuyama H., Fukuoka Y., Takeda H., Suzuki Y., Honda T. J. Heterocycl. Chem. 23:1986;185.
24. (f) Babu G., Perumal P.T. Tetrahedron Lett. 39:1998;3225.
25. Sundararajan G., Prabagaran N., Varghese B. Org. Lett. 3:2001;1973.
26. Ma Y., Qian C., Xie M., Sun J. J. Org. Chem. 64:1999;6462.
27. Kobayashi S., Komiyama S., Ishitanim H. Biotechnol. Bioeng. 61:1998;23.
28. Kobayashi S., Nagayama S. J. Am. Chem. Soc. 118:1996;8977.
29. Jianheng Z., Chao-Jun L. J. Org. Chem. 67:2002;3969.
30. Yadav J.S., Reddy B.V.S., Rao R.S., Kiran S.K., Kunwar A.C. Tetrahedron. 58:2002;7891.
31. Kamal A., Rao N.V., Laxman E. Tetrahedron Lett. 38:1997;6945.
32. Kamal A., Laxman E., Arifuddin M. Tetrahedron Lett. 41:2000;7743.
33. Kamal A., Reddy B.S.N. Chem. Lett. 1998;543.
34. Kamal A., Reddy P.S.M.M., Reddy D.R.S. Tetrahedron Lett. 43:2002;6629.
35. Kamal A., Ramana K.V., Ankati H.B., Ramana A.V. Tetrahedron Lett. 43:2002;6861.
36. 1H NMR, EIMS and IR.
37. 13C, 18.06, 22.42, 25.46, 32.30, 32.68, 35.59, 53.96, 55.99, 61.01, 62.42, 72.56, 112.03, 115.02, 115.68, 121.53, 139.34, 152.67.