Regioselective Inverse Electron Demand Diels-Alder Reactions of N-Acyl 6-Amino-3-(methylthio)-1,2,4,5-tetrazines

Journal of Organic Chemistry

Volumn 63, Issue 18, 1998, Pages 6329-6337

  Boger, Dale L ^a   Schaum, Robert P ^a   Garbaccio, Robert M ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001688605     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo980795g     Document Type: Article

References (38)

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23. Cioslowski, J.; Sauer, J.; Hetzenegger, J.; Karcher, T.; Hierstetter, T. J. Am. Chem. Soc. 1993, 115, 1353. Burg, B.; Dittmar, W.; Reim, H.; Steigel, A.; Sauer, J. Tetrahedron Lett. 1975, 2897. Mueller, K.; Sauer, J. Tetrahedron Lett. 1984, 25, 2541. Balcar, J.; Chrisam, G.; Huber, F. X.; Sauer, J. Tetrahedron Lett. 1983, 24, 1481. Meier, A.; Sauer, J. Tetrahedron Lett. 1990, 31, 6855. Meresz, O.; Foster-Verner, P. A. J. Chem. Soc., Chem. Commun. 1972, 950. Sauer, J.; Heldmann, D. K. Tetrahedron 1998, 54, 4297.
24. Cioslowski, J.; Sauer, J.; Hetzenegger, J.; Karcher, T.; Hierstetter, T. J. Am. Chem. Soc. 1993, 115, 1353. Burg, B.; Dittmar, W.; Reim, H.; Steigel, A.; Sauer, J. Tetrahedron Lett. 1975, 2897. Mueller, K.; Sauer, J. Tetrahedron Lett. 1984, 25, 2541. Balcar, J.; Chrisam, G.; Huber, F. X.; Sauer, J. Tetrahedron Lett. 1983, 24, 1481. Meier, A.; Sauer, J. Tetrahedron Lett. 1990, 31, 6855. Meresz, O.; Foster-Verner, P. A. J. Chem. Soc., Chem. Commun. 1972, 950. Sauer, J.; Heldmann, D. K. Tetrahedron 1998, 54, 4297.
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29. 2 requires 190.2607).
30. Boger, D. L.; Panek, J. S.; Patel, M. Org. Synth. 1991, 70, 79.
31. 2 substituents.
32. Details of the X-ray structure determination may be found in the Supporting Information and have been deposited in the Cambridge Crystallographic Data Centre.
33. 3-Amino-6-(methylthio)-1,2,4,5-tetrazme did not react even with enamine 7b at 100°C.
34. The half-life of 2 in dioxane at 120°C was 1 day.
35. Seitz, G.; Dietrich, S.; Görge, L.; Richter, J. Tetrahedron Lett. 1986, 27, 2747.
36. Benson, S. C.; Lee, L.; Snyder, J. K. Tetrahedron Lett. 1996, 37, 5061.
37. For examples of intramolecular Diels-Alder additions with other heteroatom-tethered alkynes, see: Sietz, G.; Gorge, L.; Dietrich, S. Tetrahedron Lett. 1985, 26, 4355.
38. 2iBu) in THF at -78°C.