Unconventional acceptor and donor functional groups linked by a captodative spacer

Tetrahedron

Volumn 52, Issue 48, 1996, Pages 15197-15208

  Alcalde, Ermitas ^a   Gisbert, Maria ^a   Pons, Josep M ^a   Pérez García, Lluïsa ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

1,2,4 TRIAZOLE DERIVATIVE; BENZIMIDAZOLE DERIVATIVE; IMIDAZOLE DERIVATIVE; PYRIDINIUM DERIVATIVE;

ARTICLE; DRUG STABILITY; DRUG STRUCTURE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OXIDATION; PRIORITY JOURNAL; STRUCTURE ACTIVITY RELATION;

EID: 0030602262     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(96)00968-4     Document Type: Article

References (45)

1. 1. Heterocyclic Betaines, 32. Part 31: Alcalde, E.; Gisbert, M.; Alvarez-Rúa, C.; García-Granda, S. Tetrahedron, 1996, in press.
2. 2. Kauffmann, T. Angew. Chem. Int. Ed. Engl. 1979, 18, 1.
3. 3b-c
4. b) Elguero, J. in Comprehensive Heterocyclic Chemistry; Katritzky, A. R.; Rees, C. W. eds.; vol 5, p. 158, 168, and 268; Pergamon Press: Oxford, 1984.
5. c) Marzin, C.; Peek, M. E.; Elguero, J.; Figey, H. P.; Defay, N. Heterocycles 1977, 6, 911.
6. 4. a) Viehe, H. G.; Janousek, Z.; Merényi, R. Acc. Chem. Res. 1985, 18, 148.
7. b) Viehe, H. G.; Merényi, R.; Janousek, Z. Pure & Appl. Chem. 1988, 60, 1635.
8. c) Sustmann, R.; Korth, H.-G. Adv. Phys. Org. Chem. 1990, 26, 131.
9. 4a,b
10. b) Dewar, J.S. J. Am. Chem. Soc. 1952, 74, 3353.
11. c) Baidock, R.W. Master of Sciences Thesis, University of East Anglia, 1965.
12. d) Baldock, R.W.; Hudson, P.; Katritzky, A.R.; Soti, F. Heterocycles 1973, 1, 67.
13. e) Baldock, R.W.; Hudson, P.; Katritzky, A.R.; Soti, F. J. Chem. Soc., Perkin Trans. I 1974, 1422.
14. f) Balaban, A.T. Rev. Rom. Chim. 1971, 16, 725.
15. g) Balaban, A.T.; Caproiu, M.T.; Negoita, N.; Baican, R. Tetrahedron 1977, 2249.
16. h) Viehe, H.G.; Merényi, R.; Stella, L.; Janousek, Z. Angew. Chem. Int. Ed. Engl. 1979, 18, 917.
17. 6. Alcalde, E.; Gisbert, M.; Pérez-García, L. Tetrahedron 1995, 51, 13365, and references cited therein.
18. 6
19. b) Barlin, G.B. J. Chem. Soc.(B) 1967, 641.
20. 9 see: a) Alcalde, E. Adv. Heterocycl. Chem. 1994, 60, 197.
21. b) Alcalde, E.; Dinarés, I.; Pérez-García, L. Il Farmaco, Ed. Sci. 1996, 51, 381.
22. 9b
23. b) Abe, J.; Shirai, Y. J. Am. Chem. Soc. 1996, 118, 4705.
24. 10. Alcalde, E.; Gisbert, M.; Pérez-García, L. Chem. Lett. 1995, 865.
25. 10b
26. b) Comprehensive Supramolecular Chemistry; Atwood, J.L.; Davies, J.E.D.; Macnicol, D.D.; Vögtle, F. eds.; vol 1 and 2; Elsevier: Oxford, 1996.
27. 6
28. 13. Kirk, K.L. J. Heterocycl. Chem. 1985, 22, 57.
29. 14a,b a) Turner, R.M.; Lindell, S.D.; Ley, S.V. J. Org. Chem. 1991, 56, 5739, and references cited therein.
30. b) Turner, R.M.; Ley, S.V.; Lindell, S.D. Synlett. 1993, 748, and references cited therein.
31. 15b
32. b) Katritzky, A.R.; Slawinski, J.J.; Brunner, F. J. Chem. Soc. Perkin Trans. I 1989, 1139.
33. 16. Alcalde, E.; Dinarés, I.; Pérez-García, L.; Roca, T. Synthesis 1992, 395.
34. 17. Doyle, M.P.; DeBruyn, D.J.; Kooistra, D.A. J. Am. Chem. Soc. 1972, 94, 3659.
35. 18. Verzele, M.; Acke, M.; Anteunis, M. J. Chem. Soc. 1963, 5598.
36. 19. a) Newkome, G.R.; Taylor, H.C.R.; Fronczek, F.R.; Delord, T.J. J. Org. Chem. 1984, 49, 2961.
37. b) Newkome, G.R.; Joo, Y.J.; Evans, D.W.; Fronczek, F.R.; Baker, G.R. J. Org. Chem. 1990, 55, 5714.
38. 20. a) Olah, G.A.; Narang, S.C.; Meidar, D.; Salem, G.F. Synthesis 1981, 282.
39. b) Olah, G.A.; Iyer, P.S.; Prakash, G.K.S. Synthesis 1986, 513.
40. c) Olah, G.A.; Yamato, T.; Iyer, P.S.; Prakash, G.K.S. J. Org. Chem. 1986, 57, 2826.
41. 21. Thurkauf, A.; Jacobson, A.E.; Rice, K.C. Synthesis 1988, 233.
42. 2SO was previously dried with an activated molecular sieve (3 Å) to reduce the presence of water in the solvent.
43. 23. a) Alcalde, E.; Dinarés, I.; Frigola, J.; Jaime, C.; Fayet, J.-P.; Vertut, M.-C.; Miravitlles, C.; Rius, J. J. Org. Chem. 1991, 56, 4223.
44. b) Alcalde, E; Pérez-García, L.; Frigola, J. Chem. Pharm. Bull. 1993, 41, 614.
45. c) Alcalde, E.; Dinarés, I.; Pons, J.M.; Roca, T. J. Org. Chem. 1994, 59, 639.