A facile synthesis of fulgenic acid via base induced 1,4- dehydrobromination of (bromomethyl)methylmaleic anhydride

Synthesis

Volumn , Issue 8, 1999, Pages 1306-1308

  Deshpande, Sachin G ^a   Argade, Narshinha P ^a  

^a NATIONAL CHEMICAL LABORATORY   (India)

Author keywords

(bromomethyl)methylmaleic anhydride; 1,4 elimination; Base; Fulgenic acid

Indexed keywords

ACID ANHYDRIDE; BASE; METHYL BROMIDE; POTASSIUM HYDROXIDE;

AQUEOUS SOLUTION; ARTICLE; BROMINATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; NONHUMAN; REACTION ANALYSIS; SYNTHESIS;

EID: 0032870836     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-3558     Document Type: Article

References (32)

1. NCL Communication No. 6458.
2. (a) Dowd, P.; Trivedi, B. K.; Shapiro, M.; Marwaha, L. K. J. Chem. Soc., Perkin Trans. 2 1985, 413.
3. (b) Dowd, P.; Shapiro, M.; Kang, J. Tetrahedron 1984, 40, 3069.
4. (c) Grate, J. W.; Schrauzer, G. N. Z. Naturforsch 1984, 39B, 821.
5. (d) Dowd, P.; Trivedi, B. K.; Shapiro, M.; Marwaha, L. K. J. Am. Chem. Soc. 1976, 98, 7875.
6. (e) Dowd, P.; Shapiro, M.; Kang, K. J. Am. Chem. Soc. 1975, 97, 4754, and refs cited therein.
7. Zahorszky, U. I.; Musso, H. Justus Liebigs Ann. Chem. 1973, 1777.
8. Muramatsu, H.; Kawano, H.; Ishii, Y.; Saburi, M.; Uchida, Y. J. Chem. Soc., Chem. Commun. 1989, 769.
9. (a) Akimov, D. A.; Zheltikov, A. M.; Koroteev, N. I.; Naumov, A. N.; Sidorov-Biryukov, D. A.; Fedotov, A. B. Kvantovaya Elektron, (Moscow), 1996, 23, 871; Chem. Abstr. 1997, 126, 178 925.
10. (a) Akimov, D. A.; Zheltikov, A. M.; Koroteev, N. I.; Naumov, A. N.; Sidorov-Biryukov, D. A.; Fedotov, A. B. Kvantovaya Elektron, (Moscow), 1996, 23, 871; Chem. Abstr. 1997, 126, 178 925.
11. (b) Akimov, D. A.; Fedotov, A. B.; Koroteev, N. I.; Magnitskii, S. A.; Naumov, A. N.; Sidorv-Biryukov, D. A.; Zheltikov, A. M. Jpn. J. Appl. Phys. Part 1 1997, 36(IB), 426.
12. (c) Niikura, H. Jpn. Kokai Tokkyo Koho JP 09 269 402, 1996; Chem. Abstr. 1997, 127, 364005j.
13. (d) Perrott, C. M.; Pidgeon, K. J. PCT Int. Appl. WO 9618 927, 1996; Chem. Abstr. 1996, 125, 93652.
14. (e) Nakamura, K. Jpn. Kokai Tokkyo Koho JP 07 319 108, 1995; Chem. Abstr. 1996, 124, 160516.
15. (f) Willner, I.; Dagan, A.; Rubin, S.; Blonder, R.; Riklin, A.; Cohen, Y. Eur. Pat. Appl. EP 668 502, 1995; Chem. Abstr. 1995, 123, 222307.
16. (g) Kawahara, M.; Sayo, K.; Goto, K.; Noguchi, T.; Yamaguchi, Y.; Deki, S. US Pat. 5 371 122, 1994; Chem. Abstr. 1995, 122, 292396.
17. (h) Sugai, A. Jpn. Kokai Tokkyo Koho JP 06 130 546, 1994; Chem. Abstr. 1995, 122, 20648.
18. (i) Malcolm, L. R. Jpn. Kokai Tokkyo Koho JP 01 103 915, 1989; Chem. Abstr. 1990, 112, 45740.
19. Barney, A. L.; Stevenson, H. B. US Patent 2 870 196, 1959; Chem. Abstr. 1959, 53, 11237.
20. Bailey, W. J.; Hudson, R. L.; Yates, E. T. J. Org. Chem. 1963, 28, 828.
21. (a) Dowd, P.; Kang, K. Synth. Commun. 1974, 4, 151.
22. (b) Bellus, D., Bredow, K.; Sauter, H.; Weis, C. D. Helv. Chim. Acta 1973, 56, 3004.
23. (a) Dowd, P.; Hershline, R. J. Chem. Soc., Chem. Commun. 1986, 1409.
24. (b) Dowd, P.; Hershline, R. J. Chem. Soc., Perkin Trans. 2 1988, 61.
25. Deshpande, A. M.; Natu, A. A.; Argade, N. P. J. Org. Chem. 1998, 63, 9557.
26. (a) Garman, A. J.; Kalindjian, S. B. Fed. Eur. Biochem. Soc. Lett. 1987, 223, 361.
27. (b) Baumann, M. E.; Bosshard, H. Helv. Chim. Acta 1978, 61, 2751.
28. (a) Leung, M.; Trahanovsky, W. S. J. Am. Chem. Soc. 1995, 117, 841.
29. (b) Rabasco, J. J.; Kass, S. R. Tetrahedron Lett. 1993, 34, 765.
30. (c) Thibblin, A. J. Chem. Soc., Perkin Trans. 2 1986, 321.
31. (d) Moss, R J.; Rickborn, B. J. Org. Chem. 1986, 51, 1992.
32. (e) Hill, R. K.; Bock, M. G. J. Am. Chem. Soc. 1978, 100, 637, and refs cited therein.