Cycloaddition reactions of phthalimide substituted cyclic polyenes with heteroatom dienophiles

Journal of Heterocyclic Chemistry

Volumn 44, Issue 3, 2007, Pages 719-723

  Templin, Stephen S ^a   Wallock, Nathaniel J ^b   Bennett, Dennis W ^c   Siddiquee, Tasneem ^c   Haworth, Daniel T ^b   Donaldson, William A ^b  

^a CARDINAL STRITCH UNIVERSITY   (United States)

^b Marquette University   (United States)

^c UNIVERSITY OF WISCONSIN MILWAUKEE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

4 PHENYL 1,2,4 TRIAZOLINE 3,5 DIONE; 5 PHTHALIMIDO 8 PHENYL 8 AZA 7 OXATRICYCLO[4.2.2.0 2,4]DEC 9 ENE; 6 PHTHALIMIDOBICYCLO[5.1.0]OCTA 2,4 DIENE; 7 PHTHALIMIDO 1,3,5 CYCLOHEPTATRIENE; ALKADIENE; ALKENE DERIVATIVE; DIENOPHILE; HETEROCYCLIC COMPOUND; NITROSOBENZENE; OXYGEN; PHENYL GROUP; PHTHALIMIDE; PHTHALIMIDE DERIVATIVE; POLYENE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLOADDITION; PROTON NUCLEAR MAGNETIC RESONANCE; REGIOCHEMISTRY; STEREOCHEMISTRY; SUBSTITUTION REACTION; X RAY CRYSTALLOGRAPHY;

EID: 38949174024     PISSN: 0022152X     EISSN: None     Source Type: Journal    
DOI: 10.1002/jhet.5570440334     Document Type: Article

References (44)

1. Cookson, R. C.; Gilani, S. S. H.; Stevens, I. D. R. Tetrahedron Lett. 1962, 615.
2. Wichterle, O. Collect. Czech. Chem. Commun. 1947, 12, 292.
3. Vogt, P. F.; Miller, M. J. Tetrahedron 1998, 54, 1317.
4. (a) Surman, M. J.; Miller, M. J. J. Org. Chem. 2001, 66, 2466.
5. (b) Surman, M. J.; Mulvihill, M. J.; Miller, M. J. J. Org. Chem. 2002, 67, 4115.
6. (a) Shireman, B. T.; Miller, M. J. J. Org. Chem. 2001, 66, 4809.
7. (b) Lee, W.; Miller, M. J. J. Org. Chem. 2004, 69, 4516.
8. (c) Li, F.; Brogan, J. B.; Gage, J. L.; Zhang, D.; Miller, M. J. J. Org. Chem. 2004, 69, 4538.
9. (d) Li, F.; Warshakoon, N. C.; Miller, M. J. J. Org. Chem. 2004, 69, 8836.
10. (a) Yao, M.-L.; Adiwidjaja, G.; Kaufmann, D. E. Angew. Chem., Int. Ed. 2002, 41, 3375.
11. (b) Pineschi, M.; Del Moro, F.; Crotti, P.; Macchia, F. Org. Lett. 2005, 7, 3605.
12. (a) Hart, H.; Ramaswami, S. K.; Willer, R. J. Org. Chem. 1979, 44, 1.
13. (b) Becker, Y.; Eisenstadt, A.; Shvo, Y. J. Organomet. Chem. 1978, 155, 63.
14. (c) Gresze, G.; Schulz, G. Tetrahedron 1961, 12, 7.
15. Ren, H.; Grady, S.; Gamenara, D.; Heinzen, H.; Moyna, P.; Croft, S. L.; Kendrick, H.; Yardley, V.; Moyna, G. Bioorg. Med. Chem. Lett. 2001, 11, 1851.
16. (a) Sander, M.; Dehmlow, E. V. Eur. J. Org. Chem. 2001, 399.
17. (b) Banwell, M. G.; Corbett, M.; Gulbis, J.; Mackay, M. F.; Reum, M. E. J. Chem. Soc., Perkin Trans. 1, 1993, 945.
18. (c) Schuster, D. I.; Wang, L.; Van der Veen, J. M. J. Am. Chem. Soc. 1985, 107, 7045.
19. (d) Oda, M.; Morita, N.; Asao, T. Tetrahedron Lett. 1980, 21, 471.
20. (e) Adam, W.; Erden, I.; Cox, O. J. Org. Chem. 1979, 44, 861.
21. (a) Oda, M.; Okawa, K.; Tsuri, H.; Kuroda, S. Tetrahedron 2003, 59, 795.
22. (b) Brecht, R.; Haenel, F.; Seitz, G.; Frenzen, G.; Pilz, A.; Massa, W.; Wocadlo, S. Liebigs Ann. 1997, 851.
23. (c) Adam, W.; Grabowski, S.; Hinz, R. F.; Lucchini, V.; Peters, E. M.; Peters, K.; Rebollo, H.; Von Schnering, H. G. Chem. Ber. 1987, 120, 2075.
24. (d) Balci, M.; Atasoy, B. Tetrahedron Lett. 1984, 25, 4033.
25. (e) Welt, G.; Wolf, E.; Fischer, P.; Foehlisch, B. Chem. Ber. 1982, 115, 3427.
26. (f) Adam, W.; Cueto, O.; De Lucchi, O. Chem. Ber. 1982, 115, 1170.
27. (g) Adam, W.; Balci, M.; Pietrzak, B. J. Am. Chem. Soc. 1979, 101, 6285.
28. (h) Betz, W.; Daub, J.; Rapp, K. M. Liebigs Ann. 1975, 2089.
29. (a) Wallock, N. J.; Donaldson, W. A. J. Org. Chem. 2004, 69, 2997.
30. (b) Yun, Y. K.; Godula, K.; Cao, Y.; Donaldson, W. A. J. Org. Chem. 2003, 68, 901.
31. Nedra, W. S.; Elliott, I. W. J. Org. Chem. 1962, 27, 1445.
32. (a) Yamamoto, Y.; Momiyama, N.; Yamamoto, H. J. Am. Chem. Soc. 2004, 126, 5962.
33. (b) Anson, C. E.; Hartmann, S.; Kelsey, R. D.; Stephenson, G. R. Polyhedron 2000, 19, 569.
34. (c) Russi, S.; Pardo, H.; Heinzen, H.; Dias, E.; Moyna, P.; Mariezcurrena, R. A.; Suescun, L.; Mombru, A. W. Acta Cryst. Sec. C 2000, C56, 672.
35. (d) Russi, S.; Mombru, A. W.; Gamenara, D.; Dias, E.; Heinzen, H.; Moyna, P.; Faccio, R.; Suescun, L.; Mariezcurrena, R. A. Acta Cryst. Sec. E 2001, E57, o444.
36. 1H NMR spectrum of 8b at 23°C consisted of broad signals due to slow rotation about the benzamide bond; at 60°C the spectrum was considerably sharper.
37. Signal assignments were facilitated by COSY correlations.
38. (a) Kresze, G.; Firl, J. Tetrahedron Lett. 1965, 1163.
39. (b) Streith, J.; Augelmann, G.; Fritz, H.; Strub, H. Tetrahedron Lett. 1982, 23, 1909.
40. For the X-ray crystal structure of 6 see: Bennett, D. W.; Siddiquee, T. A.; Haworth, D. T.; Wallock, N. J.; Donaldson, W. A. J. Chem. Cryst. 2003, 33, 209.
41. (a) Reich, H. J.; Ciganek, E.; Roberts, J. D. J. Am. Chem. Soc. 1970, 92, 5166.
42. (b) Hall, G. E.; Roberts, J. D. J. Am. Chem. Soc. 1971, 93, 2203.
43. (c) Klump, K. N.; Chesick, J. P. J. Am. Chem. Soc. 1963, 85, 130.
44. (d) Gorlitz, M.; Gunther, H. Tetrahedron 1969, 25, 4467.