Facile synthesis of carboxylic anhydrides using 4,5-dichloro-2-[(4-nitrophenyl)sulfonyl]pyridazin-3(2H)-one

Synthesis

Volumn , Issue 10, 2003, Pages 1517-1520

  Kim, Jeum Jong ^a   Park, Yong Dae ^a   Song Lee, Woo ^b   Cho, Su Dong ^a   Yoon, Yong Jin ^a  

^a Gyeongsang National University   (South Korea)

^b Korea Research Institute of Bioscience and Biotechnology (KRIBB)   (South Korea)

Author keywords

4,5 dichloro 2 4 nitrophenyl)sulfonyl pyridazin 3(2H) one; Carboxylic anhydride; Sulfonyl transfer

Indexed keywords

AROMATIC COMPOUNDS; HYDRIDES; ORGANIC SOLVENTS; SYNTHESIS (CHEMICAL);

ANHYDRIDES;

CARBOXYLIC ACIDS;

4,5 DICHLORO 2 [(4 NITROPHENYL)SULFONYL]PYRIDAZIN 3(2H) ONE; ACID ANHYDRIDE; ALIPHATIC COMPOUND; AROMATIC COMPOUND; CARBOXYLIC ACID; CARBOXYLIC ANHYDRIDE; ORGANIC SOLVENT; PYRIDAZINE DERIVATIVE; UNCLASSIFIED DRUG;

ACYLATION; ARTICLE; CHEMICAL REACTION; REACTION ANALYSIS; SYNTHESIS; TEMPERATURE;

EID: 0042244167     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-40512     Document Type: Article

References (37)

1. (a) Ogliaruso, M. A.; Wolfe, J. F. Synthesis of Carboxylic Acids, Esters and Their Derivatives; Wiley: New York, 1991, 198-217.
2. (b) Mariella, R. P.; Brown, K. H. Can. J. Chem. 1971, 49, 3348.
3. (c) Shambhu, M. B.; Digenis, G. A. J. Chem. Soc., Chem. Commun. 1974, 619.
4. (d) Tamura, Y.; Kirihara, M.; Sasho, M.; Akai, S.; Sekihachi, J.; Okunaka, R.; Kita, Y. J. Chem. Soc., Chem. Commun. 1987, 1474.
5. (e) Holzapfel, C. W.; Pettit, G. R. J. Org. Chem. 1985, 50, 2323.
6. (f) Fukuoka, S.; Takimoto, S.; Katsuki, T.; Yamaguchi, M. Tetrahedron Lett. 1987, 28, 4711.
7. (g) Tamura, Y.; Kirihara, M.; Sekihachi, J.; Okunaka, R.; Mohri, S.; Tsugoshi, T.; Akai, S.; Sasho, M.; Kita, Y. Tetrahedron Lett. 1987, 28, 3971.
8. (h) Bryson, T. A.; Roth, G. A. Tetrahedron Lett. 1986, 27, 3689.
9. Fife, W. K.; Zhang, Z. Tetrahedron Lett. 1986, 27, 4937.
10. Adduci, J. M.; Ramirez, R. S. Org. Prep. Proced. Int. 1970, 2, 321.
11. (a) Rinderknecht, H.; Ma, V. Helv. Chim. Acta 1964, 47, 162.
12. (b) Rinderknecht, H.; Gutein, M. Org. Syn. Coll. 5; Wiley: New York, 1973, 822.
13. (c) Remigiusz, K.; Juliatiek, R.; Shahriar, M. J. Org. Chem. 1994, 59, 2913.
14. (a) Mestres, R.; Palomo, C. Synthesis 1981, 218.
15. (b) Burton, S. G.; Kaye, P. T. Synth. Commun. 1989, 19, 3331.
16. Keshavamurthy, K. S.; Vankar, Y. D.; Dhar, D. N. Synthesis 1982, 506.
17. (a) Hata, T.; Tajima, K.; Mukaiyama, T. Bull. Chem. Soc. Jpn. 1968, 41, 2746.
18. (b) Chen, F. M. F.; Benoiton, N. L. Synthesis 1979, 710.
19. (a) Eglinton, G.; Jones, E. R. H.; Shaw, B. L.; Whiting, M. C. J. Chem. Soc. 1954, 1860.
20. (b) Edman, J. R.; Simmons, H. E. J. Org. Chem. 1968, 33, 3808.
21. (c) Newman, M. S.; Togue, M. W. J. Org. Chem. 1971, 36, 1398.
22. (d) Kita, Y.; Akai, S.; Yoshigi, M.; Nakajima, Y.; Yasuda, H.; Tamura, Y. Tetrahedron Lett. 1984, 25, 6027.
23. (e) Kita, Y.; Akai, S.; Ajimura, N.; Yoshigi, M.; Tsugoshi, T.; Yasuda, H.; Tamura, Y. J. Org. Chem. 1986, 51, 4150.
24. Rambacher, P.; Make, S. Angew. Chem. 1968, 80, 487.
25. Sandler, S. R.; Karo, W. Organic Functional Group Preparations, Vol. 12; Academic Press: New York, 1972, Chap. III.
26. Blankemeyer-Menge, B.; Nimtz, M.; Frank, R. Tetrahedron Lett. 1990, 31, 1701.
27. Jorba, X.; Albericio, F.; Grandas, A.; Bannwarth, W.; Giralt, E. Tetrahedron Lett. 1990, 31, 1915.
28. (a) Katritzky, A. R.; Shobana, N.; Pernak, J.; Afridi, A. S.; Fan, W.-Q. Tetrahedron 1992, 48, 7817.
29. (b) Wakasugi, K.; Nakamura, A.; Tanabe, Y. Tetrahedron Lett. 2001, 42, 7427.
30. (c) Katritzky, A. R.; He, A. Y.; Suzuki, K. J. Org. Chem. 2000, 65, 8210.
31. Kweon, D. H.; Kim, H. K.; Kim, J. J.; Chung, H.-A.; Lee, W. S.; Kim, S. K.; Yoon, Y. J. J. Heterocycl. Chem. 2002, 39, 203.
32. Kang, Y. J.; Chung, H.-A.; Kim, J. J.; Yoon, Y. J. Synthesis 2002, 733.
33. 14
34. The Merck Index; Merck & Co., Inc.: New Jersey, 1983, 10th ed., 156.
35. Katritzky, A. R.; Shobana, N.; Pernak, J.; Afridi, A. S.; Fan, W.-Q. Tetrahedron 1992, 48, 7817.
36. Pollock, J. A. R.; Stevens, R. Dictionary of Organic Compounds, Vol. 3; Oxford University Press: Oxford, 1965, 1592.
37. Kita, Y.; Akai, S.; Yoshigi, M.; Nagajima, Y.; Yasuda, H.; Tamura, Y. Tetrahedron Lett. 1984, 25, 6027.