Two novel 1,2,4,5-tetrazines that participate in inverse electron demand Diels-Alder reactions with an unexpected regioselectivity

Journal of Organic Chemistry

Volumn 71, Issue 1, 2006, Pages 185-193

  Hamasaki, Akiyuki ^a   Ducray, Richard ^a   Boger, Dale L ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ELECTROCHEMISTRY; SYNTHESIS (CHEMICAL);

DIELS-ALDER REACTIONS; ELECTRON DEMAND; REGIOSELECTIVITY;

ORGANIC COMPOUNDS;

1,2,4,5 TETRAZINE DERIVATIVE; 3 (BENZYLOXYCARBONYL)AMINO 6 METHYLSULFINYL 1,2,4,5 TETRAZINE; 3 METHYLSULFINYL 6 METHYLTHIO 1,2,4,5 TETRAZINE; SULFOXIDE; TETRAZINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CYCLOADDITION; DIELS ALDER REACTION; ELECTRON; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SYNTHESIS;

AZO COMPOUNDS; ELECTRONS; MOLECULAR STRUCTURE;

EID: 31144460318     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo051832o     Document Type: Article

References (33)

1. Boger, D. L.; Weinreb, S. M. Hetero Diels-Alder Methodology in Organic Synthesis; Academic Press: San Diego, CA, 1987.
2. Reviews: Boger, D. L. Tetrahedron 1983, 39, 2869.
3. Boger, D. L. Chan. Rev. 1986, 86, 781.
4. Boger, D. L. Chemtracts: Org. Chem. 1996, 9, 149.
5. Streptonigrin: Boger, D. L.; Panek, J. S.; Duff, S. R. J. Am. Chem. Soc. 1985, 107, 5745.
6. OMP: Boger, D. L.; Coleman, R. S.; Panek, J. S.; Yohannes, D. J. Org. Chem. 1984, 49, 4405.
7. Lavendamycin: Boger, D. L.; Duff, S. R.; Panek, J. S.; Yasuda, M. J. Org. Chem. 1985, 50, 5790.
8. PDE-I and PDE-II: Boger, D. L.; Coleman, R. S. J. Am. Chem. Soc. 1987, 109, 2717.
9. CC-1065: Boger, D. L.; Coleman, R. S. J. Am. Chem. Soc. 1988, 110, 1321, 4796.
10. Prodigiosin: Boger, D. L.; Patel, M. J. Org. Chem. 1988, 53, 1405.
11. Trikentrin A: Boger, D. L.; Zhang, M. J. Am. Chem. Soc. 1991, 113, 4230.
12. Isochrysohermidin: Boger, D. L.; Baldino, C. M. J. Am. Chem. Soc. 1993, 115, 11418.
13. Ningalin A, Lamellarin O, Lukianol A, and Storniamide A: Boger, D. L.; Boyce, C. W.; Labroli, M. A.; Sehon, C. A.; Jin, Q. J. Am. Chem. Soc. 1999, 121, 54.
14. Phomazarin: Boger, D. L.; Hong, J.; Hikota, M.; Ishida, M. J. Am. Chem. Soc. 1999, 121, 2471.
15. Ningalin B: Boger, D. L.; Soenen, D. R.; Boyce, C. W.; Hedrick, M. P.; Jin, Q. J. Org. Chem. 2000, 65, 2479.
16. Anhydrolycorinone and related alkaloids: Boger, D. L.; Wolkenberg, S. E. J. Org. Chem. 2000, 65, 9120.
17. Roseophilin: Boger, D. L.; Hong, J. J. Am. Chem. Soc. 2001, 123, 8515.
18. Ningalin D: Hamasaki, A.; Zimpleman, J. M.; Hwang, I.; Boger, D. L. J. Am. Chem. Soc. 2005, 127, 10767.
19. Dimethyl 1,2,4,5-tetrazine-3,6-dicarboxylate (1): Sauer, J.; Mielert, A.; Lang, D.; Peter, D. Chem. Ber. 1965, 98, 1435.
20. Boger, D. L.; Coleman, R. S.; Panek, J. S.; Huber, F. X.; Sauer, J. J. Org. Chem. 1985, 50, 5377.
21. Boger, D. L.; Panek, J. S.; Patel, M. Org. Synth. 1991, 70, 79.
22. 3,6-Bis(methylthio)-1,2,4,5-tetrazine (2): Sandström, J. Acta Chem. Scand. 1961, 15, 1575.
23. Boger, D. L.; Sakya, S. M. J. Org. Chem. 1988, 53, 1415.
24. 3,6-Bis(3,4-dimethoxybenzoyl)-1,2,4,5-tetrazine: Soenen, D. R.; Zimpleman, J. M.; Boger, D. L. J. Org. Chem. 2003, 68, 3593.
25. 3-Methoxy-6-methylthio-1,2,4,5-tetrazine: Sakya, S. M.; Groskopf, K. K.; Boger, D. L. Tetrahedron Lett. 1997, 38, 3805.
26. N-Acyl-6-amino-3-methylthio-1,2,4,5-tetrazine (e.g., 3): Boger, D. L.; Schaum, R. P.; Garbaccio, R. M. J. Org. Chem. 1998, 63, 6329.
27. Johnson, J. L.; Whitney, B.; Werbel, L. M. J. Heterocycl. Chem. 1980, 17, 501.
28. Seitz, G.; Dietrich, S.; Görge, L.; Richter, J. Tetrahedron Lett. 1986, 27, 2747.
29. Blair, L. K.; Baldwin, J.; Smith, W. C., Jr. J. Org. Chem. 1977, 42, 1817.
30. Atomic coordinates for 7c (CCDC 282318), 7f (CCDC 282319), 7g (CCDC 282321), and 9c (CCDC 282320) have been deposited with the Cambridge Crystallographic Data Centre.
31. Sega, T.; Pollak, A.; Stanovnik, B.; Tisler, M. J. Org. Chem. 1973, 38, 3307.
32. Cazeau, P.; Duboudin, F.; Moulines, F.; Babot, O.; Dunogues, J. Tetrahedron 1987, 43, 2075.
33. Stork, G.; Brizzolara, A.; Landesman, H.; Szmuszkovic, J.; Terrell, R. J. Am. Chem. Soc. 1963, 85, 207.