Synthesis of new mesomeric betaines containing a triazolopyridiniumolate system and their unexpected function as masked isocyanates

Heterocycles

Volumn 53, Issue 2, 2000, Pages 265-270

  Sakai, Norio ^a   Funabashi, Makoto ^a   Minakata, Satoshi ^a   Ryu, Ilhyong ^a   Komatsu, Mitsuo ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLENE DERIVATIVE; BETAINE DERIVATIVE; ISOCYANIC ACID DERIVATIVE; PYRIDINIUM DERIVATIVE;

ALKYLATION; ARTICLE; CHEMICAL ANALYSIS; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; SYNTHESIS;

EID: 0034141581     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/com-99-8760     Document Type: Article

References (21)

1. For selected reviews on mesomeric betaines, see; W. D. Ollis and S. P. Stanforth, Tetrahedron, 1985, 41, 2239; C. A. Ramsden, 'Advances in Heterocyclic Chemistry,' Vol. 26, ed. by A. R. Katritzky and A. J. Boulton, 1980, p. 1.
2. For selected reviews on mesomeric betaines, see; W. D. Ollis and S. P. Stanforth, Tetrahedron, 1985, 41, 2239; C. A. Ramsden, 'Advances in Heterocyclic Chemistry,' Vol. 26, ed. by A. R. Katritzky and A. J. Boulton, 1980, p. 1.
3. For selected reviews on 1,3-dipolar cycloadditions, see; A. Padwa, '1,3-Dipolar Cycloaddition Chemistry,' Vols. I and II, John Wiley & Sons, New York, 1984; B. M. Trost and I. Fleming, 'Comprehensive Organic Synthesis, ' Vol. 4, Pergamon Press, New York. 1991, pp. 1069-1168.
4. For selected reviews on 1,3-dipolar cycloadditions, see; A. Padwa, '1,3-Dipolar Cycloaddition Chemistry,' Vols. I and II, John Wiley & Sons, New York, 1984; B. M. Trost and I. Fleming, 'Comprehensive Organic Synthesis, ' Vol. 4, Pergamon Press, New York. 1991, pp. 1069-1168.
5. J. S. Glas by, 'Encyclopedia of the Alkaloids,' Vols. I and II, Plenum Press, New York, 1975.
6. For selected reviews on [1,2,4]triazolo[4,3-α]pyridines, see; S. W. Schneller, 'Comprehensive Heterocyclic Chemistry I,' Vol. 5, ed. by K. T. Potts, Pergamon Press, Oxford, 1984, pp. 847-903; G Jones and D. R. Sliskovic, 'Advances in Heterocyclic Chemistry,' Vol. 34, ed. by A. R. Katritzky, 1983, pp. 80-143.
7. For selected reviews on [1,2,4]triazolo[4,3-α]pyridines, see; S. W. Schneller, 'Comprehensive Heterocyclic Chemistry I,' Vol. 5, ed. by K. T. Potts, Pergamon Press, Oxford, 1984, pp. 847-903; G Jones and D. R. Sliskovic, 'Advances in Heterocyclic Chemistry,' Vol. 34, ed. by A. R. Katritzky, 1983, pp. 80-143.
8. S. W. Schneller, 'Comprehensive Heterocyclic Chemistry I,' Vol. 5, ed. by K. T. Potts, Pergamon Press, Oxford, 1984, pp. 903-904; D. R. Sliskovic, 'Comprehensive Heterocyclic Chemistry II,' Vol. 8, ed. by G. Jones, Pergamon Press, Oxford, 1996, pp. 385-388.
9. S. W. Schneller, 'Comprehensive Heterocyclic Chemistry I,' Vol. 5, ed. by K. T. Potts, Pergamon Press, Oxford, 1984, pp. 903-904; D. R. Sliskovic, 'Comprehensive Heterocyclic Chemistry II,' Vol. 8, ed. by G. Jones, Pergamon Press, Oxford, 1996, pp. 385-388.
10. B. C. Bishop, H. Marley, K. J. McCullough, P. N. Preston, and S. H. B. Wright, J. Chem. Soc., Perkin Trans. 1, 1993, 705; I. Ya. Postovskii, S. K. Kotovskaya, and A. V. Polonyankin, Chem. Abstr., 1980, 93, 46529; K. T. Potts and H. R. Burton, J. Org. Chem., 1966, 31, 251.
11. B. C. Bishop, H. Marley, K. J. McCullough, P. N. Preston, and S. H. B. Wright, J. Chem. Soc., Perkin Trans. 1, 1993, 705; I. Ya. Postovskii, S. K. Kotovskaya, and A. V. Polonyankin, Chem. Abstr., 1980, 93, 46529; K. T. Potts and H. R. Burton, J. Org. Chem., 1966, 31, 251.
12. B. C. Bishop, H. Marley, K. J. McCullough, P. N. Preston, and S. H. B. Wright, J. Chem. Soc., Perkin Trans. 1, 1993, 705; I. Ya. Postovskii, S. K. Kotovskaya, and A. V. Polonyankin, Chem. Abstr., 1980, 93, 46529; K. T. Potts and H. R. Burton, J. Org. Chem., 1966, 31, 251.
13. M. Komatsu, M. Kobayashi, S. Itoh, and Y. Ohshiro, J. Org. Chem., 1993, 58, 6620; N. Sakai, M. Funabashi, T. Hamada, S. Minakata, I. Ryu, and M. Komatsu, Tetrahedron, 1999, 55, 13703.
14. M. Komatsu, M. Kobayashi, S. Itoh, and Y. Ohshiro, J. Org. Chem., 1993, 58, 6620; N. Sakai, M. Funabashi, T. Hamada, S. Minakata, I. Ryu, and M. Komatsu, Tetrahedron, 1999, 55, 13703.
15. K. T. Potts, H. R. Burton, and S. K. Roy, J. Org. Chem., 1966, 31, 265.
16. 3O: 135.0433 Found: 135.0428.
17. 9: C, 58.94; H, 4.55; N, 8.25. Found: C, 59.10; H, 4.46; N, 8.22.
18. -1, graphite monochromated CuKα (λ = 1.54178 Å), T = 14 °C. Final discrepancy factor: R = 0.052 and Rw = 0.058.
19. H. Barnighausen, F. Jellinek, J. Munnik, and A. Vos, Acta. Crystallogr., 1963, 16, 471.
20. -1, graphite monochromated MoKα (λ = 0.71069 Å), T = 23 °C. Final discrepancy factor: R = 0.110 and Rw = 0.116.
21. 14. The structures of 4a and 6a were solved by the direct method (SHELEX-86).