A novel double 'inverse electron-demand' Diels-Alder reaction of azolyldienamines and tetrazines

Tetrahedron Letters

Volumn 40, Issue 34, 1999, Pages 6313-6316

  Kotschy, András ^a   Novák, Zoltán ^a   Vincze, Zoltán ^a   Smith, David M ^b   Hajós, György ^c  

^a EÖTVÖS LORÁND UNIVERSITY   (Hungary)

^b UNIVERSITY OF ST ANDREWS   (United Kingdom)

^c CHEMICAL RESEARCH CENTER   (Hungary)

Author keywords

Dieis Alder reactions; Dienamines; Pyridazines; Tetrazines

Indexed keywords

PYRIDAZINE DERIVATIVE; TETRAZINE DERIVATIVE;

ARTICLE; MOLECULAR INTERACTION; NUCLEAR OVERHAUSER EFFECT; REACTION ANALYSIS; SYNTHESIS;

BETULACEAE;

EID: 0033588153     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01184-3     Document Type: Article

References (12)

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2. Kotschy, A.; Timári, G.; Hajós, Gy.; Messmer, A. J. Org. Chem. 1996, 61, 4423-4426.
3. Boger, D. L.; Panek, J. S.; Patel, M. Org. Synth. 1992, 70, 79-82.
4. Kotschy, A.; Smith, D. M.; Bényei, A. Cs. Tetrahedron Lett. 1998, 39, 1045-1048.
5. A similar reaction of 2,3-dimethyl-1,3-butadiene and 3,6-bis-trifluoromethyl-tetrazine has also been reported: Klindert, T.; von Hagel, P.; Baumann, L.; Seitz G. J. Prakt. Chem. 1997, 339, 623.
6. A similar reaction has been published where oxidation of the intermediate was postulated. Borthakur, D. R.; Prajapati, D.; Sandhu, J. S. Heterocycles 1987, 26, 337-341.
7. Brown, H. C; Cheng, M. T.; Parcell, L. J.; Pilipovich, D. J. Org. Chem. 1961, 26, 4407; Barlow, M. G.; Haszeldine, R. N.; Picket, J. A. J Chem. Soc., Perkin Trans. 1 1978, 363-366.
8. Brown, H. C; Cheng, M. T.; Parcell, L. J.; Pilipovich, D. J. Org. Chem. 1961, 26, 4407; Barlow, M. G.; Haszeldine, R. N.; Picket, J. A. J Chem. Soc., Perkin Trans. 1 1978, 363-366.
9. Geldard, J. F.; Lions, F. J. Org. Chem. 1965, 30, 318-320.
10. Hajós, Gy.; Kotschy, A. Acta Chim. Slov. 1998, 45, 285-354.
11. Hierstetter, T.; Tischler, B.; Sauer, J. Tetrahedron Lett. 1992, 33, 8019-8022.
12. z: 0.16, 0.22), respectively.