One-pot synthesis of novel (2-Oxo-1,2-dihydropyridin-3-yl)-1,3,5- triazine derivatives from methyl 2-(N- triphenylphosphoranylidene)aminonicotinate, aryl isocyanates and primary amines: Sequential aza-wittig /cycloaddition / ring-transformation reactions

Tetrahedron

Volumn 53, Issue 47, 1997, Pages 16061-16082

  Okawa, Tomohiro ^a   Osakada, Naoto ^a   Eguchi, Shoji ^a   Kakehi, Akikazu ^b  

^a NAGOYA UNIVERSITY   (Japan)

^b SHINSHU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

(2 OXO 1,2 DIHYDROPYRIDIN 3 YL) 1,3,5 TRIAZINE DERIVATIVE; AMINE; ISOCYANIC ACID DERIVATIVE; METHYL 2 (N TRIPHENYLPHOSPHORANYLIDENE)AMINONICOTINIC ACID; NICOTINIC ACID DERIVATIVE; TRIAZINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; PRIORITY JOURNAL; REACTION ANALYSIS;

LIGUSTRUM VULGARE;

EID: 0030658062     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)10064-3     Document Type: Article

References (31)

1. Barluenga, F.; Palacios, F. Org. Prep. Proced. Int. 1991, 23, 1.
2. Eguchi, S.; Matsushita, Y. Yamashita, K. Org. Prep. Proced Int. 1992, 24, 209.
3. Molina, P.; Vilaplana, M. J. Synthesis 1994, 1197.
4. Wamhoff, H.; Rechardt, G.; Stölben, S. Advances in Heterocyclic Chemistry 1996, Vol. 64, 159.
5. Okawa, T.; Sugimori, T.; Eguchi, S.; Kakehi, A. Chem. Lett., 1996, 843 and references cited therein.
6. O'Neil, I. A.; Murray, C. L.; Potter, A. J.; Kalindjian, S. B. Tetrahedron Lett., 1997, 38, 3609.
7. Eguchi, S.; Yamashita, K.; Matsushita, Y.; Kakehi, A. J. Org. Chem. 1995, 60, 4006.
8. Molina, P.; Díaz, I.; Tárraga, A. Tetrahedron, 1995, 51, 5617.
9. Eguchi, S.; Suzuki, T.; Okawa, T.; Matsushita, Y.; Yashima, E.; Okamoto, Y. J. Org. Chem. 1996, 61, 7316.
10. Sugimori, T.; Okawa, T.; Eguchi, S.; Yashima, E.; Okamoto, Y. Chem. Lett. 1997, 869.
11. He, F.; Snider, B. B. Synlett, 1997, 483.
12. Peinador, C.; Moreira, M. J., Quintela, J. M. Tetrahedron 1994, 50, 6705.
13. Saito, T.; Tsuda, K. Tetrahedron Lett. 1996, 37, 9071.
14. Watanabe, M.; Okada, H.; Teshima, T.; Noguchi, M.; Kakehi, A. Tetrahedron 1996, 52, 2827.
15. Noguchi, M.; Okada, H.; Watanabe M.; Okuda, K.; Nakamura, O. Tetrahedron 1996, 52, 6581.
16. Jin, J.; Weinreb, S. M. J. Am. Chem. Soc. 1997, 119, 2050.
17. Nitta, M.; Iino, Y.; Mori, S.; Takayasu, T. J. Chem. Soc., Perkin Trans. 1 1995, 1001 and references cited therein.
18. Palacios, F.; Alonso, C.; Rubiales, G. J. Org. Chem. 1997, 62, 1146.
19. Okawa, T.; Eguchi, S. Synlett 1994, 555.
20. Okawa, T.; Eguchi, S.; Kakehi, A. J. Chem. Soc. Perkin Trans. 1 1996, 247.
21. Okawa, T.; Kawase, M.; Eguchi, S. Synthesis in press.
22. Okawa, T.; Eguchi, S.; Tetrahedron Lett. 1996, 37, 81.
23. Related reference: Taylor, E. C.; Dowling, J. E. J. Org. Chem. 1997, 62, 1599 and references cited therein.
24. Appel, R.; Halstenberg, M. In Organophosphorus Reagents in Organic Synthesis; Cadogan, J. I. G., Ed.; Academic Press: London, 1979; pp 378ff.
25. We thank Shiratori Parmaceutical Co., Ltd. for a gift of DMC.
26. Takuma, S.; Hamada, Y.; Shioiri, T. Chem. Pharm. Bull. 1982, 30, 3147 and reference cited therein.
27. Wamhoff, H.; Schmidt, A. J. Org. Chem. 1993, 58, 6976.
28. Molina, P.; Alajarn, M.; Vidal, A. Tetrahedron 1989, 45,4263.
29. Bödeker, J.; Courault, K.; Köckritz, A.; Köckritz, P. J. Pract. Chem., 1983, 463.
30. For example, pKa of pyrazine is 0.6 at 20 °C and pka of pyridine is 5.42 at 25 °C by Kagaku Binran.
31. 1/2] on the nitrogen of pyrazine having 3-ester and 2-carbodiimide functions was 0.253 and that on the nitogen of pyridine having same substituents was 0.485 by PM3 calculation.