Extraordinary formation of a novel butadiene derivative, (Z,E)-1-(2-naphthylmethyloxycarbonyl-amino) -2,4-bis (4-nitrophenyl)butadiene, and subsequent isomerization into the corresponding (E,E)-isomer

Journal of Organic Chemistry

Volumn 63, Issue 21, 1998, Pages 7516-7519

  Li, Min ^a,c   Kar, Leela ^b   Johnson, Michael E ^a  

^a Center for Pharmaceutical Biotechnology   (United States)

^b UNIVERSITY OF ILLINOIS AT CHICAGO   (United States)

^c MERCK RESEARCH LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000351318     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9802426     Document Type: Article

References (13)

1. Fastrez, J.; Jespers, L.; Lison, D.; Renard, M.; Sonveaux, E. Tetrahedron Lett. 1989, 30, 6861-6864.
2. Cheng, L.; Goodwin, C. A. Tetrahedron Lett. 1991, 32, 7333-7336.
3. Wang, C.-L. J.; Taylor, T. L.; Mical, A. J.; Spitz, S.; Reilly, T. M. Tetrahedron Lett. 1992, 33, 7667-7670.
4. Oleksyszyn, J.; Boduszek, B.; Kam, C.-M.; Powers, J. C. J. Med. Chem. 1994, 37, 226-231.
5. Chen, R.-Y.; Dan, S.-C. Phosphorus, Sulfur, Silicon 1991, 56, 39-48.
6. Lethbridge, A.; Norman, R. O. C.; Thomas, C. B. J. Chem. Soc., Perkin 1 1973, 35-38.
7. The 2D COSY and ROESY experimental parameters and results (Figures 3-5) are included in the Supporting Information for this paper. However, some key ROESY cross-peaks observed in a mixture of 4 and 5 are summarized in Table 1.
8. 8b
9. (a) Mitchell, J. B.; Nandi, C. L.; McDonald, I. K.; Thornton, J. M.; Price, S. L. J. Mol. Biol 1994,239,315-331.
10. (b) Levitt, M.; Perutz, M. F. J. Mol. Biol. 1988, 201, 751-754.
11. Li, M.; Johnson, M. E. Synth. Commun. 1995, 25, 533-537.
12. Loev, B.; Kormendy, M. F.; Goodman, M. M. Organic Syntheses; Wiley and Sons: New York, 1973; Collect. Vol. V, pp 162-166.
13. Strassburg, R. W.; Gregg, R. A.; Walling, C. J. Am. Chem. Soc. 1947, 69, 2141-2143.