Diheteroarylmethanes. 6. Probing the electron-withdrawing rank of heteroaryl groups by conformational studies of push-pull ethylenes. Isolation of NH-enamine tautomers of α,α-diheteroarylacetaldehydes (heteroaryl = 2-benzoxazolyl, 2-benzothiazolyl)

Journal of Organic Chemistry

Volumn 61, Issue 5, 1996, Pages 1770-1778

  Abbotto, Alessandro ^a   Bradamante, Silvia ^a   Capri, Natale ^a   Rzepa, Henry ^b   Williams, David J ^b   White, Andrew ^b  

^a UNIVERSITY OF MILAN   (Italy)

^b IMPERIAL COLLEGE LONDON   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000998809     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo951885d     Document Type: Article

References (38)

1. For part 5, see ref 2. For part 4, see ref 5.
2. Abbotto, A.; Bradamante, S.; Pagani, G. A. J. Org. Chem. 1996, 61, 1761-1769.
3. Abbotto, A.; Bradamante, S.; Pagani, G. Gazz. Chim. Ital. 1994, 124, 301-308.
4. (a) Abbotto, A.; Alanzo, V.; Bradamante, S.; Pagani, G. A. J. Chem. Soc., Perkin Trans. 2 1991, 481-488.
5. (b) Abbotto, A.; Bradamante, S.; Pagani, G. A. J. Org. Chem. 1993, 58, 444-448.
6. (c) Abbotto, A.; Bradamante, S.; Pagani, G.; Rzepa, H.; Stoppa, F. Heterocycles 1994, 40, 757-776.
7. (d) Bradamante, S.; Pagani G. A. Pure Appl. Chem. 1989, 61, 709-716.
8. (e) Barchiesi, E.; Bradamante, S.; Ferraccioli, R.; Pagani, G. A. J. Chem. Soc., Perkin Trans. 2 1990, 375-383.
9. (f) Abbotto, A.; Bradamante, S.; Pagani, G. A. J. Org. Chem. 1993, 58, 449-455.
10. Bradamante, S.; Facchetti, A.; Pagani, G. Gazz. Chim. Ital. In press.
11. (a) Sandstrom, J. In Topics in Stereochemistry; Allinger, N. L., Eliel, E. L., Wilen, S. H., Eds.; John Wiley and Sons: New York, 1983; Vol. 14.
12. (b) Kleinpeter, E.; Spitzner, R.; Schroth, W. Magn. Reson. Chem. 1987, 25, 688-695.
13. (c) Kleinpeter, E.; Spitzner, R.; Schroth, W.; Pihlaja, K. J. Prakt. Chem. 1990, 332, 841-844.
14. (d) Kleinpeter, E.; Schroth, W. Magn. Reson. Chem. 1991, 29, 223-230.
15. (e) Kleinpeter, E.; Thomas, S.; Uhlig, G.; Rudorf, W. D. Magn. Reson. Chem. 1993, 31, 714-721.
16. Abdulla, R. F ; Brinkmeyer, R. S. Tetrahedron 1979, 35, 1675-1735.
17. Breitmaier, E.; Voelter, W. Carbon-13 NMR Spectroscopy; VCH: Weinheim, 1987; p 247.
18. Budzelaar, P. H. M. geNMR, NMR Simulation Program, IvorySoft, Amsterdam, 1993.
19. Günther, H. NMR Spectroscopy. An Introduction; J. Wiley and Sons: Chichester, 1980; p 247.
20. Stewart, J J. P. MOPAC 6.0. 1990, QCPE Program 455.
21. Klamt, A.; Shuurmann, G. J. Chem. Soc., Perkin Trans. 2 1993, 799.
22. (a) Klingsberg, E. J. Org. Chem. 1966, 31, 3489-3493.
23. (b) Klingsberg, E. J. Heterocycl. Chem. 1966, 3, 243-243.
24. (c) Klingsberg, E. Chem. Ind. 1968, 51, 1813-1814.
25. (d) Stavaux, M.; Lozac'h, N. Bull. Soc. Chim. Fr. 1968, 10, 4273-4274.
26. (e) Stavaux, M. Bull. Soc. Chim. Fr. 1971, 12, 4429-4434.
27. (f) Klingsberg, E. J Org. Chem. 1972, 37, 3226-3229.
28. (g) Kristensen, R.; Sletten, J. Acta Chem. Scand. 1973, 27, 2517-2523.
29. Abbotto, A.; Alanzo, V.; Bradamante, S.; Pagani, G. A.; Rizzoli, C.; Calestani, G. Gazz. Chim. Ital. 1991, 121, 365-368.
30. Reference 6a, p 155.
31. (a) Ramos, M. T.; Avendan̄o, C.; Elguero, J.; Jimeno, M. L.; Bellanato, J.; Florencio, F.; Aparicio, J. S. Heterocycles 1989, 29, 165-181.
32. (b) Avendano, C.; Ramos, M T.; Elguero, J.; Jimeno, M. L.; Bellanato, J.; Florencio, F. Can. J. Chem. 1988, 66, 1467-1473.
33. Ramos, M. T.; Avendan̄o, C.; Elguero, J.; Jimeno, M. L. Bull. Soc. Chim. Belg. 1989, 98, 497-501.
34. (a) Mondelli, R.; Merlini, L. Tetrahedron 1966, 22, 3253-3273.
35. (b) More O'Ferrall, R. A.; Murray, B A. J. Chem. Soc., Perkin Trans. 2 1994, 2461-2470.
36. Rai, C.; Braunwarth, J. B. J. Org. Chem. 1961, 26, 3434.
37. Rai, C.; Braunwarth, J. B. U.S Patent 3,250,780; Chem. Abstr. 1966, 65, 7180g.
38. The author has deposited atomic coordinates for this structure with the Cambridge Crystallographic Data Centre. The coordinates can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road. Cambridge, CB2 1EZ, UK.