Synthesis of 2,6-disubstituted pyrido[2,3-b][1,4]oxazines

Tetrahedron

Volumn 65, Issue 36, 2009, Pages 7403-7407

  Nishiwaki, Nagatoshi ^a   Hisaki, Masataka ^b   Ono, Masaki ^b   Ariga, Masahiro ^b  

^a ANAN NATIONAL COLLEGE OF TECHNOLOGY   (Japan)

^b OSAKA KYOIKU UNIVERSITY   (Japan)

Author keywords

3 Nitro 2 pyridone; O Alkylation; Pyridoxazine; Reductive cyclization; Ring transformation

Indexed keywords

3 METHYL 5 NITROPYRIMIDIN 4(3H) ONE; 3 NITRO 2 PYRIDONE; 4 METHYL 2 PENTANONE; 4 METHYLACETOPHENONE; ACETOPHENONE DERIVATIVE; CARBON; OXAZINE DERIVATIVE; PYRID[2,3 B][1,4]OXAZINE; PYRIDONE DERIVATIVE; PYRIMIDINONE DERIVATIVE; UNCLASSIFIED DRUG;

ACYLATION; ALKYLATION; ARTICLE; CHEMICAL REACTION; CYCLIZATION; O ALKYLATION; PRIORITY JOURNAL; RING TRANSFORMATION; SYNTHESIS;

EID: 67949105151     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2009.07.024     Document Type: Article

References (44)

1. Nishiwaki N., and Ariga M. In: Eguchi S. (Ed). Topics in Heterocyclic Chemistry (2007), Springer, Berlin 43-72
2. Gomorov S.P. Heterocycles 53 (2000) 1607
3. van der Plas H.C. In: Katritzky A.R. (Ed). Advances in Heterocyclic Chemistry Vol. 74 (1999), Academic, London
4. Nishiwaki N., Yamashita K., Azuma M., Adachi T., Tamura M., and Ariga M. Synthesis (2004) 1996
5. Nishiwaki N., Ohtomo H., Tamura M., Hori K., Tohda Y., and Ariga M. Heterocycles 55 (2001) 1581
6. Nishiwaki N., Adachi T., Matsuo K., Wang H.-P., Matsunaga T., Tohda Y., and Ariga M. J. Chem. Soc., Perkin Trans. 1 (2000) 27
7. Caliendo G., Perissutti E., Santagada V., Fiorino F., Severino B., Bianca R., d'Emmanuele di V., and LippSorrentino R. Bioorg. Med. Chem. 10 (2002) 2663
8. Macchiarulo A., Costantino G., Fringuelli D., Vecchiarelli A., Schiaffella F., and Fringuelli R. Bioorg. Med. Chem. 10 (2002) 3415
9. Matsumoto Y., Tsuzuki R., Matsuhisa A., Yoden T., Yamagiwa Y., Yanagisawa I., Shibanuma T., and Nohira H. Bioorg. Med. Chem. 8 (2000) 393
10. Belliotti T.R., Wustrow D.J., Brink W.A., Zoski K.T., Shih Y.-H., Whetzel S.Z., Georgic L.M., Corbin A.E., Akunne H.C., Heffner T.G., Pugsley T.A., and Wise L.D. J. Med. Chem. 42 (1999) 5181
11. Matsumoto Y., Tsuzuki R., Matsuhisa A., Masuda N., Yamagiwa Y., Yanagisawa I., Shibanuma T., and Nohira H. Chem. Pharm. Bull. 47 (1999) 971
12. Savelon L., Bizot-Espiard J.G., Caignard D.H., Pfeiffer B., Renard P., Viaud M.C., and Guillaumet G. Bioorg. Med. Chem. 6 (1998) 133
13. Buckman B., Mohan R., Koovakkat S., Liang A., Trinh L., and Morrissey M.M. Bioorg. Med. Chem. Lett. 8 (1998) 2235
14. Bartoloméa J.M., Alcázar J., Andrés J.I., De Bruyn M., Fernández J., Matesanz E., and Van Emelen K. Tetrahedron Lett. 44 (2003) 8545
15. Balko T.W., and Brinkmeyer R.S. J. Heterocycl. Chem. 24 (1987) 901
16. Heilmann D., and Sicker D. Chem.-Ztg. 115 (1991) 219
17. Heilmann D., and Sicker D. J. Prakt. Chem. 332 (1990) 265
18. Cho S.-D., Park Y.-D., Kim J.-J., Lee S.-G., Ma C., Song S.-Y., Joo W.H., Falck J.R., Shiro M., Shin D.-S., and Yoon Y.-J. J. Org. Chem. 68 (2003) 7918
19. Anderson W.K., and Dalvie D.K. J. Heterocycl. Chem. 30 (1993) 1533
20. Calvo, R.R.; Wing, C.S.; Player, M.R. PCT Int. Appl. WO 2006058338, 2006;
21. Chem. Abstr. 145 (2006) 8035
22. 6-Aryl PyOAs as partial structures of tetracyclic compounds having serotonin 5-HT2c activity: Fu, J.-M. PCT Int. Appl. WO 2003033497, 2003;
23. Chem. Abstr. 138 (2003) 314609
24. 6-Alkyl PyOAs as partial structures of tricyclic compounds having antiviral activity: Wathen, M.W.; Wathen, L.K. PCT Int. Appl. WO 2004019933, 2004;
25. Chem. Abstr. 140 (2004) 229445
26. Anderson, D.J.; Beauchamp, T.J.; Bundy, G.L.; Ciske, F.L.; Farrell, J.R.; Graber, D.R.; Genin, M.J.; Judge, T.M.; Moon, M.W.; Schnute, M.E.; Strohbach, J.W.; Thaisrivongs, S.; Thorarensen, A.; Turner, S.R.; Vaillancourt, V.A.; Wolf, A.J. PCT Int. Appl. WO 2002004445, 2002;
27. Chem. Abstr. 136 (2002) 118477
28. 6-Ethynyl and 6-carbamoyl PyOAs: O'Brien, P.M. PCT Int. Appl. WO 2004014389, 2004;
29. Chem. Abstr. 140 (2004) 175189
30. 6-Carbamoyl PyOAs: Takaishi, H.; Katsuhira, T.; Yamaguchi, H.; Kawabata, Y.; Harayama, H.; Oda, Y.; Murai, M. PCT Int. Appl. WO 2000006549, 2000;
31. Chem. Abstr. 132 (2000) 151835
32. Shusherina N.P., Likhomanova T.I., and Adamskaya E.V. Chem. Heterocycl. Compd. 14 (1978) 57
33. Aubert C., Betschmann P., Eichberg M.J., Gandon V., Heckrodt T.J., Lehmann J.L., Malacria M., Masjost B., Paredes E., Vollhardt K.P.C., and Whitener G.D. Chem.-Eur. J. 13 (2007) 7443
34. Dai W., Peterson J.L., and Wang K.K. Org. Lett. 8 (2006) 4665
35. Twin H., and Batey R.A. Org. Lett. 6 (2004) 4913
36. Ruda M.C., Bergman J., and Wu J. J. Comb. Chem. 4 (2002) 530
37. Liu H., Ko S.-B., Josien H., and Curran D.P. Tetrahedron Lett. 36 (1995) 8917
38. Volle J.-N., Mävers U., and Schlosser M. Eur. J. Org. Chem. (2008) 2430
39. Ukrainets I.V., Bereznyakova N.L., Parshiov V.A., and Turov A.V. Chem. Heterocycl. Compd. 43 (2007) 1269
40. Kainmüller E.K., Ollé E.P., and Bannwarth W. Chem. Commun. (2005) 5459
41. Lanni E.L., Bosscher M.A., Ooms B.D., Shandro C.A., Ellsworth B.A., and Anderson C.E. J. Org. Chem. 73 (2008) 6425
42. Matsumoto K., Ikemi Y., Suda M., Iida H., and Hamana H. Heterocycles 72 (2007) 187
43. Mukhopadhyay C., and Tapaswi P.K. Tetrahedron Lett. 49 (2008) 6237
44. Oliveria-Campos A.M.F., Salaheldin A.M., and Rodrigues L.M. Arkivoc xvi (2007) 92