Synthesis of ω-(1,1,3-trioxo-1,3-dihydrobenzo[d]isothiazol-2-yl)- alkanecarboxylic acids: Conventional versus microwave heating

Arkivoc

Volumn 2007, Issue 4, 2007, Pages 312-319

  Soler, Lucía ^a   Cerrada, Verónica ^a   Matía, M Paz ^a   Novella, J Luis ^a   Alvarez Builla, Julio ^a  

^a UNIVERSITY OF ALCALÁ   (Spain)

Author keywords

Microwaves; Saccharin alkylation; (1,1,3 trioxo 1,3 dihydrobenzo d isothiazol 2 yl) alkanecarboxylic acids

Indexed keywords

EID: 33846116103     PISSN: 1551-7012     EISSN: 14246376     Source Type: Journal    
DOI: 10.3998/ark.5550190.0008.428     Document Type: Article

References (29)

1. Remsen, I.; Fahlberg, C. Ber. 1879, 12, 469.
2. (b) Ager, D. J.; Pantaleone, D. P.; Henderson, S. A.; Katritzky, A. R.; Prakash, I.; Walters, D. E. Angew. Chem. Int. Ed. 1998, 37, 1802.
3. Dompert, W. U. Ger. Patent 3321969, 1984.
4. Berryman, K. A.; Bunker, A. M.; Doherty, A. M.; Edmunds, J. J. WO Patent, 96/26195, 1996
5. (a) Groutas, W. C.; Houser-Archield, N.; Chong, L. S.; Venkataraman, R. K.; Epp, J. B.; Huang H.; McClenahan J. J. J. Med. Chem. 1993, 36, 3178.
6. (b) Hlasta, D. J.; Subramanyan, C.; Bell, M. R.; Carabateas, P. M.; Court, J. J.; Desai, R. C.; Drozd, M. L.; Eickhoff, W. M.; Ferguson, E. W.; Gordon, R. J.; Johnson, J. A.; Kumar, V.; Maycock, A. L.; Mueller, K. R.; Pagani, E. D.; Robinson, D. T.; Saindane, M. T.; Silver, P. J.; Subramanian, S. J. Med. Chem. 1995, 38, 739.
7. Bazán, N. G.; Alvarez-Builla, J.; US Patent 5621110, 1997.
8. Achilles, K.; Schirmeister, T.; Otto, H. H. Arch. Pharm. 2000, 333, 243.
9. Sbovoda, J.; Palecek, J.; Dedek, V. Coll. Czech. Chem. Commun. 1986, 51, 1304.
10. Svoboda, J.; Palecek, J.; Dedek, V. Coll. Czech. Chem. Commun. 1986, 51, 1133.
11. (a) Lombardino, J. G. US Patent 4289879, 1981.
12. (b) Lombardino, J. G.; Wiseman, E. H.; McLamore, W. H. J. Med. Chem. 1971, 14, 1171.
13. (c) Zinnes, H.; Sircar, J. C.; Lindo, N. A.; Schwartz, M. L.; Fabian, A. C.; Shavel, J. Jr.; Kasulanis, C. F.; Genzer, J. D.; Lutomski, C.; DiPasquale, G. J. Med. Chem. 1982, 25, 12.
14. Zinnes, R. H.; Schwartz, G. M.; Shavel, M. J. DE Patent 2208351, 1972.
15. (b) Lombardino, J. G.; Wiseman, E. H. J. Med. Chem. 1971, 14, 973.
16. (a) Da Settimo, A.; Primofiore, G.; La Motta, C.; Da Settimo, F.; Simorini, F.; Boldrini, E.; Bianchini, P. Farmaco 1996, 51, 261.
17. (b) Primofiore, G.; Da Settimo, F.; La Motta, C.; Simorini, F.; Minutolo, A.; Boldrini, E. Farmaco 1997, 52, 583.
18. Park, M.-S.; Yun, M.-S.; Kim, M.-K.; Kwon, S.-K. Yakhak Hoechi 2001, 45, 570.
19. Ding, J.; Gu, H.; Wen, J.; Lin, C. Synth. Commun. 1994, 24, 301.
20. Caliendo, G.; Fiorino, F.; Perissutti, E.; Severino, B.; Scolaro, D.; Gessi, S.; Cattabriga, E.; Borea, P. A.; Santagada, V. Eur. J. Pharm. Sci. 2002, 16, 15.
21. (a) Hayes, B. L. Microwave Synthesis: Chemistry at the Speed of Light CEM: Matthews, 2002, p 33.
22. (b) Kappe, C. O., Stadler, A., Microwaves in Organic and Medicinal Chemistry, Wiley-VCH Verlag GmbH: Weinheim 2005, p 16.
23. Magidson, O. J.; Gorbachov, S. W. Ber. 1923, 56B, 1810.
24. Giam, C. S.; Lockhart, R. A. Org. Prep. Proc. Int. 1974, 6, 1.
25. Chapman, J. M.; Cocolas, G. H.; Hall, I. H. J. Med. Chem. 1983, 26, 243.
26. Abe, K.; Tsukamoto, Y.; Ishimura, A. Yakugaku Zasshi 1953, 73, 1319.
27. Svoboda, J.; Palecek, J.; Dedek, V. Coll. Czech. Chem. Commun. 1986, 51, 1304.
28. Reid, E. E.; Rice, L. M.; Grogan, C. H. J. Am. Chem. Soc. 1955, 77, 5628.
29. Blanco, M.; Perillo, I. A.; Schapira, C. B. J. Heterocyclic Chem. 1995, 32, 145.