The azaphilic addition of organometallic reagents on tetrazines: Scope and limitations

Tetrahedron

Volumn 60, Issue 9, 2004, Pages 1991-1996

  Faragó, János ^a   Novák, Zoltán ^a   Schlosser, Gitta ^b   Csámpai, Antal ^a   Kotschy, András ^a  

^a EÖTVÖS LORÁND UNIVERSITY   (Hungary)

^b CHEMICAL RESEARCH CENTER   (Hungary)

Author keywords

Aromatic nucleophilic substitution; Azaphilic addition; Reduction; Tetrazines

Indexed keywords

ORGANOMETALLIC COMPOUND; TETRAZINE DERIVATIVE;

ADDITION REACTION; ARTICLE; COMPLEX FORMATION; MOLECULAR STABILITY; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; REDUCTION;

EID: 1042287057     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2004.01.013     Document Type: Article

References (35)

1. Sauer J. Boulton A.J., Katritzky A.R., Rees C.W., Scriven E.F. 1,2,4,5-tetrazines in comprehensive heterocyclic chemistry II. 1996;901-955 Pergamon, New York.
2. Boger D.L., Weinreb S.M. Hetero Diels-Alder methodology in organic synthesis. 1997;Academic, New York.
3. Schirmer, U.; Wuerzer, B.; Meyer, N.; Neugebauer; F. A., Fischer, H. DE Patent No. 3508214, 1986; Chem. Abstr. 1987, 106, 45718.
4. Zambach, W.; Naef, R.; Trah, S.; Jeanguenat, A.; Eberle, M.; Steiger, A. WO Patent Appl. 0078739, 2000; Chem. Abstr. 2001, 134, 71613.
5. Chavez D.E., Hiskey M.A. J. Energ. Mater. 174:1999;357-377.
6. Panek J.S., Zhu B. Tetrahedron Lett. 37:1996;8151-8154.
7. Sauer J., Pabst G.R., Holland U., Kim H.-S., Loebbecke S. Eur. J. Org. Chem. 2001;697-706.
8. Stehl A., Seitz G., Schulz K. Tetrahedron. 58:2002;1343-1354.
9. Boger D.L., Wolkenberg S.E. J. Org. Chem. 65:2000;9120-9124.
10. Boger D.L., Hong J. J. Am. Chem. Soc. 123:2001;8515-8519.
11. Nomak R., Snyder J.K. Tetrahedron Lett. 42:2001;7929-7933.
12. Kotschy A., Bényei A.C., Smith D.M. Tetrahedron Lett. 39:1998;1045-1048.
13. Counotte-Potman A., van der Plas H.C., van Veldhuizen B. J. Org. Chem. 46:1981;2138-2141. and references cited therein.
14. Novák Z., Bostai B., Csékei M., Lorincz K., Kotschy A. Heterocycles. 2004;. in press.
15. Benson S.C., Lee L., Yang L., Snyder J.K. Tetrahedron. 56:2000;1165-1180.
16. Yang X., Seitz G. Arch. Pharm. (Weinheim). 325:1992;563-564.
17. Sakya S.M., Groskopf K.K., Boger D.L. Tetrahedron Lett. 38:1997;3805-3808. and references therein.
18. Glidewell C., Lighfoot P., Royles B.J.L., Smith D.M. J. Chem. Soc., Perkin Trans. 2. 1997;1167. and references therein.
19. Latosh N.I., Rusinov G.L., Ganebnykh I.N., Chupakin O.N. Russ. J. Org. Chem. 35:1999;1363-1371.
20. Mangia A., Bartesi F., Amendola U. J. Heterocycl. Chem. 14:1977;587-590.
21. Yamanaka H., Ohba S. Heterocycles. 31:1990;895-909.
22. Novák Z., Kotschy A. Org. Lett. 5:2003;3495-3497.
23. Wilkes M.C. J. Heterocycl. Chem. 28:1991;1163-1164.
24. Neugebauer F.A., Krieger C., Fischer H., Siegel R. Chem. Ber. 116:1983;2261-2274.
25. Hunter D., Neilson D.G. J. Chem. Soc., Perkin Trans. 1. 1984;2779-2783.
26. Neugebauer F.A., Siegel R. Chem. Ber. 118:1985;2157-2163.
27. Hunter D., Neilson D.G., Weakley T.J.R. J. Chem. Soc., Perkin Trans. 1. 1985;2709-2712.
28. Coburn M.D., Buntain G.A., Harris B.W., Hiskey M.A., Lee K.-Y., Ott D.G. J. Heterocycl. Chem. 28:1991;2049-2050.
29. Tetrazines that bear a substituent enabling them to act as bidentate ligands are known to be good complex forming agents. For example: Constable E.C., Housecroft C.E., Kariuki B.M., Kelly N., Smith C.B. Inorg. Chem. Commun. 5:2002;199-202.
30. Canac Y., Levoirier E., Lubineau A. J. Org. Chem. 66:2001;3206-3210.
31. Bailey W.J., Marktscheffel F. J. Org. Chem. 25:1960;1797-1800.
32. Krisnamurthy S., Brown H.C. J. Org. Chem. 44:1979;3678-3682.
33. Sneeden R.P.A., Zeiss H.H. J. Organomet. Chem. 22:1970;713-722.
34. Although careful reinvestigation of the analogous reaction of 1 with butyllithium revealed that minor amounts (<2%) of 12 are also formed in the process demonstrating the presence of the same chemistry, we believe that the formation of significant amounts of 12 in entries 22-25 and the transformation of 8a into 13a occur by different mechanism.
35. Bowie R.A., Gardner M.D., Neilson D.G., Watson K.M., Mahmood S., Ridd V. J. Chem. Soc., Perkin Trans. 1. 1972;2395-2399.