Synthesis and reactions of haloazodienes. A new and general synthesis of substituted pyridazines

Journal of Organic Chemistry

Volumn 61, Issue 25, 1996, Pages 8921-8934

  South, Michael S ^a,b   Jakuboski, Terri L ^a,b   Westmeyer, Mark D ^a,b   Daniel, R ^a,b  

^a Dukesherer Ceregen Division of Monsanto Corporation   (United States)

^b PFIZER INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

PYRIDAZINE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030470880     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo960029e     Document Type: Article

References (25)

1. Clarke, S. J.; Gilchrist, T. L. J. Chem. Res., Synop. 1985, 310-311.
2. Clarke, S. J.; Davies, D. E.; Gilchrist, T. L. J. Chem. Soc., Perkin Trans, l 1983, 1803-1807.
3. Gilchrist, T. L.; Richards, P. Synthesis 1983, 153-154.
4. Faragher, R.; Gilchrist, T. L. J. Chem. Soc., Perkin Trans, l 1979, 249-257.
5. Sommer, S. Chem. Lett. 1977, 583-586.
6. Sommer, S. Tetrahedron Lett. 1977, 117-120.
7. Sommer, S. Angew. Chem. 1977, 89, 59-60.
8. Faragher, R.; Gilchrist, T. L. J. Chem. Soc., Chem. Commun. 1976, 581-582.
9. Attanasi, O. A.; Caglioti, L. Org. Prep. Proced. Int. 1986, 28, 299-327.
10. Several attempts have been made to aromatize a tetrahydropyridazine to a pyridazine, but none involve the use of a chloroazodiene as an intermediate (see also references 1 and 11). Vors, J. P. J. Heterocycl. Chem. 1990, 27, 579-582.
11. Cocco, M. T.; Congiu, C.; Maccioni, A.; Plumitallo, A. Gazz. Chim. Hal. 1988, 118, 187-191.
12. Attanasi, O. A.; Filippone, P.; Giovagnoli, D.; Mei, A. Synth. Commun. 1994, 24, 453-461.
13. Pyridazines exhibit "bleaching" herbicidal activity.
14. (a) South, M. S.; Miller, M. J. U.S. Patent Application Pending.
15. (b) South, M. S. U.S. Patent 5, 484, 761.
16. South, M. S.; Moedritzer, K. A. U.S. Patent 5, 536, 701.
17. South, M. S.; Jakuboski, T. L. U.S. Patent Application Pending.
18. Two reports of a cycloaddition reaction involving a chloroazodiene have appeared, but these products were not elaborated to pyridazines (see also reference 15). Gilchrist, T. L.; Sanchez Romero, O. A.; Wasson, R. C. J. Chem. Soc., Perkin Trans, l 1989, 353-359.
19. Gilchrist, T. L.; Stevens, J. A.; Parton, B. J. Chem. Soc., Perkin Trans, l 1985, 1741-1745.
20. A preliminary communication has appeared. South, M. S.; Jakuboski, T. L. Tetrahedron Lett. 1995, 5703-5706.
21. Mason, J. W. In Chemistry ofHeterocydic Compounds: a Series of Monographs, Vol. 28: Pyridazines; Castle, R. N., Ed.; Interscience: New York, 1973; p 407.
22. A preliminary communication has appeared. South, M. S.; Jakuboski, T. L.; Westmeyer, M. D.; Dukesherer, D. R. Tetrahedron Lett. 1996, 1351-1354.
23. Gilchrist, T. L.; Stevens, J. A.; Parton, B. J. Chem. Soc., Perkin Trans, l 1985, 1737-1740.
24. The electron rich olefms were synthesized by published procedures (see also the Experimental Section). March, J. Advanced Organic Chemistry: Reactions, Mechanisms, and Structures, 3rd ed.; John Wiley and Sons, Inc.: New York, 1985; pp 689, 796-8.
25. It is also possible that the pyridazines may also bo formed by a concerted mechanism.