Direct conversion of heteroaromatic esters to methyl ketones with trimethylaluminum: Nonsymmetrically disubstituted 1,2,4,5-tetrazines

Journal of Organic Chemistry

Volumn 63, Issue 26, 1998, Pages 10063-10068

  Girardot, Marc ^a   Nomak, Rana ^a   Snyder, John K ^a  

^a Boston University   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETONE; ALUMINUM DERIVATIVE; ESTER; TETRAZINE DERIVATIVE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; NUCLEAR OVERHAUSER EFFECT; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 0032567304     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9815352     Document Type: Article

References (62)

1. (a) Benson, S. C.; Palabrica, C. A.; Snyder, J. K. J. Org. Chem. 1987, 52, 4610-4614. For other reports of inverse electron demand Diels-Alder reactions of indole with 1,2,4,5-tetrazines
2. (b) Seitzj G.; Kaempchen, T. Arch. Pharm. (Weinheim, Ger.) 1976, 309, 679-681.
3. Takahashi, M.; Ishida, H.; Kohmoto, M. Bull. Chem. Soc. Jpn. 1976, 49, 1725-1726.
4. Seitz, G.; Mohr, R. Chem. Zeit. 1987, 111, 81-82.
5. (e) Pindur, U.; Kim, M.-H. Tetrahedron Lett. 1988, 29, 3927-3928.
6. (f) Pindur, U.; Pfeufier, L.; Km, M.-H. Helv. Chim. Acta 1989, 72, 65-72.
7. (g) Haider, N.; Wanko, R. Heterocydes 1994, 38, 1805-1811.
8. (h) Haider, N. Acta Chim Slav. 1994,41, 205-217.
9. Benson, S. C.; Lee, L.; Snyder, J. K. Tetrahedron Lett. 1996, 37, 5061-5064.
10. (a) Basha, A.; Lipton, M. F.; Weinreb, S. M. Tetrahedron Lett. 1977, 4171-4174.
11. (b) Lipton, M. F.; Weinreb, S. M. In Org. Synth., Collect Vol. VI.; Noland, W. E., Ed.; John Wiley & Sons: New York, 1988; pp 492-495.
12. Sidler, D. R.; Lovelace, T. C.; McNamara, J. M.; Reider, P. J. J. Org. Chem. 1994, 59, 1231-1233.
13. For reviews of 1,2,4,5-tetfazine preparations: (a) Wiley, P. F. In Chemistry of 1,2,3-Triazines, and 1,2,4-Triazines, Tetrazines, and Pentazines. Wiley, P. F.; Neunhoefier, H. Chemistry of Heterocyclic Compounds Monograph 33; Weissberger, A., Taylor, E. C., Eds.; WileyInterscience: New York, 1978; pp 1077-1083.
14. (b) Neunhoefler, H. In Comprehensive Heterocyclic Chemistry; Boulton, A. J., McKillop, A., Eds.; Pérgamon: Oxford, 1984; Vol. 3, pp 555-572. For some examples of unsymmetrically disubstituted 1,2,4,5-tetrazine preparations since these reviews, see
15. Mueller, K.; Sauer, J. Tetrahedron Lett. 1984, 25, 2541-2544.
16. Seitz, G.; Goegre, L.; Dietrich, S. Tetrahedron Lett. 1985,26,4355-4358.
17. (e) Gleiter, R.; Schehlmann, V.; Spanget-Larson, J.; Fischer, H.; Neugebauer, F. A. J. Org. Chem. 1988,53, 5756-5762.
18. (f) Fields, S. C.; Parker, M. H.; Erickson, W. R. J. Org. Chem. 1994, 59, 8284-8287.
19. (g) Panek, J. S.; Zhu, B. Tetrahedron Lett. 1996, 37, 8151-8154.
20. (h) Sakya, S.; Groskopf, K K.; Boger, D. L. Tetrahedron Lett. 1997, 38, 3805-3808.
21. Boger, D. L.; Schaum, R. P.; Garbaccio, R. M. J. Org. Chem. 1998, 63, 6329-6337.
22. (j) Sauer, J.; Heldmann, D. K. Tetrahedron 1998, 54, 4297-4312.
23. For reviews of inverse electron demand Diels-Alder reactions, see: (a) Boger, D. L. Tetrahedron 1983, 39, 2869-2939.
24. (b) Boger, D. L. Chem. Rev. 1986, 86, 781-793.
25. Boger, D. L.; Weinreb, S. M. Hetero Diels-Alder Methodology in Organic Synthesis; Organic Chemistry Monograph 47; Academic: New York, 1987; Chapter 10. Recent overview
26. Boger, D. L. J. Heterocycl. Chem. 1996,33, 1519-1531.
27. Some examples, (a) streptonegrin synthesis: Boger, D. L.; Panek, J. P. J. Am. Chem. Soc. 1985, 707, 5745-5754.
28. (b) Prodigiosin synthesis: Boger, D. L.; Patel, M. Tetrahedron Lett. 1987, 28, 2499-2402;
29. Boger, D. L.; Patel, M. J. Org. Chem. 1988, 53, 1405-1415.
30. PDE-I and -II synthesis: Boger, D. L.; Coleman, R. S. J. Org. Chem. 1986,51, 3250-3252.
31. Boger, D. L.; Coleman, R. S. J. Am. Chem. Soc. 1987, 709, 2717-2727.
32. Daly, K.; Nomak, R.; Snyder, J. K. Tetrahedron Lett. 1997, 38, 8611-8614.
33. We have used analogous NOE's in the past to assign regioisomers of heterocycles derived from indole cycloadditions, ref 6, also: Benson, S. C.; Gross, J. L.; Snyder, J. K J. Org. Chem. 1990, 55, 3257-3269.
34. For the use of trialkylaluminum reagents to alkylate ketones and aldehydes: (a) Meisters, A.; Mole, T. Aust. J. Chem. 1974, 27, 1655-1663.
35. (b) Starowieyski, K. B.; Becalska, A.; Okninski, A. J. Organomet. Chem. 1985,293, 7-17.
36. Teague, S. J. Tetrahedron Lett. 1996, 37, 5751-5754.
37. (a) Boger, D. L.; Coleman, R. S.; Panek, J. S.; Huber, F. X.; Sauer, J. J. Org. Chem. 1985,50, 5377-5379.
38. (b) Boger, D. L.; Panek, J. S.; Patel, M. Org. Synth. 1991, 70, 79-92.
39. Dewar, M. J. S.; Olivella, S.; Stewart, J. J. P. J. Am. Chem. Soc. 1986,108, 5771-5779.
40. Rubottom, G. M.; Kim, C.-w. J. Org. Chem. 1983, 48, 1550-1552, and references therein.
41. (a) Takai, K.; Oshima, K.; Nozaki, H. Bull. Chem. Soc. Jpn. 1981, 54, 1281-1282.
42. (b) Wakamatsu, K.; Okuda, Y.; Oshima, K.; Nozaki, H. Bull. Chem. Soc. Jpn. 1985,58, 2425-2426.
43. Ishibashi, H.; Takamuro, I.; Mizukami, Y.; Irie, M.; Ikeda, M. Synth. Commun. 1989, 79, 443-452.
44. Arisawa, M.; Torisawa, Y.; Nakagawa, M. Synthesis 1995,1371-1372.
45. (e) Arisawa, M.; Torisawa, Y.; Kawahara, M.; Yamanaka, M.; Nishida, A.; Nakagawa, M. J. Org. Chem. 1997, 62, 4327-4329.
46. Nahm, S.; Weinreb, S. M. Tetrahedron Lett. 1981, 22, 3815-3818.
47. (a) Tolstikov, G. A.; Valitov, F. Kh.; Kuchin, A. V. Dokl. Chem. (Engl. Trans.) 1982, 265, 1406-1410.
48. (b) Shimizu, M.; Kume, K.; Fujisawa, T. Tetrahedron Lett. 1995, 36, 5227-5230.
49. (a) Pasynkiewicz, S.; Kozerski, L.; Grabowski, B. J. Organomet. Chem. 1967,8, 233-238.
50. (b) Kikkawa, L; Yorifuji, T. Synthesis 1980, 877.
51. Tolstikov, G. A.; Valitov, F. Kh.; Kuchin, A. V. J. Gen. Chem. USSR (Engl. Transi.) 1982, 52, 1170-1175 and references therein
52. Boger, D. L.; Hong, J. J. Am. Chem. Soc. 1998, 120, 1218-1222.
53. (a) Baba, Y. Bull. Chem. Soc. Jpn. 1968, 41, 1022-1023.
54. (b) Allen, P. E. M.; Bateup, B. O.; Casey, B. A. J. Organomet. Chem. 1971, 29,185-193.
55. Starowieyski, K. B.; Pasynkiewicz, S.; Sporzynski, A.; Wisniewska, K. J. Organomet. Chem. 1976,117, Cl - C3. 'Exhaustive alkylation of carboxylic acids with trialkylaluminum reagents
56. Meisters, A.; Mole, T. Aust. J. Chem. 1974,27, 1665-1672.
57. Previous synthesis: (a) Konno, S.; Fujimura, S.; Yamanaka, H. Heterocycles 1984, 22, 2245-2248.
58. (b) Ohba, S.; Konno, S.; Fujimura, S.; Yamanaka Chem. Pharm. Bull. 1991, 39, 486-488.
59. (a) Schmidt, D.; Druey, J. Helv. Chim. Acta 1955, 38, 1560-1564.
60. (b) Elix, J. A.; Wilson, W. S.; Warrener, R. N.; Calder, l.Aust. J. Chem. 1972, 55, 865-874.
61. Reimann, E.; Zeigen, H.-L. Liebigs Ann. Chem. 1976, 1351-1356.
62. Stork, G.; Brizzolara, A.; Landesman, H.; Szrauszkovic, J.; Terrell, R. J. Am. Chem. Soc. 1963, 55, 207-222.