On the tautomerism of 2,1,3-benzothiadiazinone S,S-dioxide and related compounds

Tetrahedron

Volumn 55, Issue 42, 1999, Pages 12405-12410

  Castro, Ana ^a   Gil, Carmen ^a   Martínez, Ana ^a  

^a INSTITUTO DE QUÍMICA MÉDICA   (Spain)

Author keywords

Benzothiazines; NMR; Tautomerism; Theoretical studies

Indexed keywords

BENZOTHIAZINE DERIVATIVE; HETEROCYCLIC COMPOUND;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL MODIFICATION; CHEMICAL STRUCTURE; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; SYNTHESIS;

EID: 0033570155     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(99)00723-1     Document Type: Article

References (19)

1. Alhambra, C.; Luque, F. J.; Estelrich, J.; Orozco, M. J. Org. Chem., 1995, 60, 969-976.
2. Luyten, I.; Pankiewicz, K. A.; Watanabe, K. A.; Chattopadhyaya, J. J. Org. Chem., 1998, 63, 1033-1040.
3. Ono, M.; Kawakami, M. J. Biochem., 1977, 81, 1247-1251.
4. Martinez, A.; Esteban, A. I.; De Clercq, E. Bioorg. Med. Chem. Lett., 1997, 7, 1031-1032.
5. Martinez, A.; Esteban, A. I.; Castro, A.; Gil, C.; Conde, S.; Andrei, G.; Snoeck, R.; Baizarini, J.; De Clercq, E. J. Med. Chem. 1999, 42, 1145-1150.
6. Goldman, R. C.; Klein, L. L. Ann. Rep. Med. Chem., 1994, 29, 155-164.
7. Elguero, J.; Marzin, C.; Katrizky, A. R.; Linda, P. The Tautomerism of Heterocycles; Academic Press: New York, 1986.
8. Castro, A.; Martinez, A. J. Chem. Soc., Perkin Trans. II, 1994, 1561-1564.
9. De la Cruz, A.; Elguero, J.; Goya, P. Martinez, A. Tetrahedron, 1992, 48, 6135-6150.
10. Elguero, J.; Goya, P.; Rozas, I.; Martinez, A. Chem. Ber., 1989, 122, 919-924.
11. Cohen, E.; Klarberg, B. J. Am. Chem. Soc., 1974, 84, 1994-2002.
12. Esteban, A. I.; Juanes, O.; Conde, S.; Martinez, A. Tetrahedron, 1994, 48, 13865-13870.
13. Elguero, J.; Jimeno, M. L.; Nieves, R.; Ochoa, C. J. Chem. Soc., Perkin Trans. II, 1988, 859-863.
14. Alkorta, I.; Garcia-Gomez, C.; Paéz, J.A.; Goya, P. J. Phys. Org. Chem., 1996, 9, 203-211.
15. Delley, B. J. Chem. Phys., 1991, 94, 7245-7250.
16. Gaussian 94, Revision B.3, Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. W.; Johnson, B. G.; Robb, M. A.; Cheeseman, J. R.; Keith, T.; Petersson, G. A.; Montgomery, J. A.; Raghavachari, K.; Al-Laham, M. A.; Zakrzewski, V. G.; Ortiz, J. V.; Foresman, J. B.; Peng, C. Y.; Ayala, P. Y.; Chen, W.; Wong, M. W.; Andres, J. L.; Replogle, E. S.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Binkley, J. S.; Defrees, D. J.; Baker, J.; Stewart, J. P.; Head-Gordon, M.; Gonzalez, C.; Pople, J. A. Gaussian, Inc., Pittsburgh PA, 1995.
17. Albert, A.; Serjeant, E.P. UV Determination of Ionization Constants; Chapman and Hall: London, 1971
18. Martinez, A.; Esteban, A. I.; Castro, A. Gil, C.; Conde, S.; Snoeck, R.; Andrei, G.; Balzarini, J.; De Clercq, E. Bioorg. Med. Chem., 1999, in press.
19. Martinez, A.; Castro, A.; Gil, C.; Segarra, V.; Miralpeix, M.; Domenech, T.; Beleta, J.; Ryder, H.; Palacios, J. M.; Miró, X.; Bonet, C.; Casacuberta, J. M.; Azorín, F.; Piña, B.; Puigdomenech, P. J. Med. Chem., 1999, submitted.