Intramolecular 1,3-dipolar cycloaddition at the periphery of heterocyclic systems. Part 3.1 A facile hydrazone-azomethine imine isomerization at the periphery of pyridine and pyrido[,2-a]pyrimidine systems

Tetrahedron

Volumn 52, Issue 3, 1996, Pages 901-914

  Sun, Bin ^a   Adachi, Kenji ^a   Noguchi, Michihiko ^a  

^a YAMAGUCHI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

PYRAZOLE DERIVATIVE; PYRIDINE DERIVATIVE; PYRIDO[1,2 A]PYRIMIDINE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; ENANTIOMER; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030038859     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(95)00949-3     Document Type: Article

References (43)

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12. As papers on acid-catalyzed hydrazone-azomethine imine isomerization and its 1,3-dipolar cycloaddiotion reaction: LeFevre, G.; Hamelin, J.; Tetrahedron Lett. 1979, 4503; LeFevre, G.; Sinbandhit, S.; Hamelin, J. Tetrahedron 1979, 35, 1821; LeFevere, G.; Hamelin, J. Tetrahedron 1980, 36, 887; Fouchet, B.; Houch, M.; Hamelin, J. Tetrahedron Lett. 1981, 22, 1333; Shimizu, T.; Hayashi, Y.; Miki, M.; Teramura, K. Bull. Chem Soc. Jpn. 1982, 55, 2456; Shimizu, T.; Hayashi, Y.; Nakano, M.; Teramura, K. Bull. Chem. Soc. Jpn. 1984, 57, 134; Norman, M. H., Heathcock, C. H. J. Org. Chem 1987, 52, 226; Shimizu, T.; Hayashi, Y.; Miki, M.; Teramura, K. J. Org. Chem. 1987, 52, 2277; Shimizu, T.; Hayashi, Y.; Miki, M.; Teramura, K. J. Heterocycl. Chem. 1990, 27, 1669; Katayama, H.; Takatsu, N.; Kitano, H.; Shimaya, Y. Chem. Pharm. Bull. 1990, 38, 1129. Also see ref. 4c) and 4d).
13. As papers on acid-catalyzed hydrazone-azomethine imine isomerization and its 1,3-dipolar cycloaddiotion reaction: LeFevre, G.; Hamelin, J.; Tetrahedron Lett. 1979, 4503; LeFevre, G.; Sinbandhit, S.; Hamelin, J. Tetrahedron 1979, 35, 1821; LeFevere, G.; Hamelin, J. Tetrahedron 1980, 36, 887; Fouchet, B.; Houch, M.; Hamelin, J. Tetrahedron Lett. 1981, 22, 1333; Shimizu, T.; Hayashi, Y.; Miki, M.; Teramura, K. Bull. Chem Soc. Jpn. 1982, 55, 2456; Shimizu, T.; Hayashi, Y.; Nakano, M.; Teramura, K. Bull. Chem. Soc. Jpn. 1984, 57, 134; Norman, M. H., Heathcock, C. H. J. Org. Chem 1987, 52, 226; Shimizu, T.; Hayashi, Y.; Miki, M.; Teramura, K. J. Org. Chem. 1987, 52, 2277; Shimizu, T.; Hayashi, Y.; Miki, M.; Teramura, K. J. Heterocycl. Chem. 1990, 27, 1669; Katayama, H.; Takatsu, N.; Kitano, H.; Shimaya, Y. Chem. Pharm. Bull. 1990, 38, 1129. Also see ref. 4c) and 4d).
14. As papers on acid-catalyzed hydrazone-azomethine imine isomerization and its 1,3-dipolar cycloaddiotion reaction: LeFevre, G.; Hamelin, J.; Tetrahedron Lett. 1979, 4503; LeFevre, G.; Sinbandhit, S.; Hamelin, J. Tetrahedron 1979, 35, 1821; LeFevere, G.; Hamelin, J. Tetrahedron 1980, 36, 887; Fouchet, B.; Houch, M.; Hamelin, J. Tetrahedron Lett. 1981, 22, 1333; Shimizu, T.; Hayashi, Y.; Miki, M.; Teramura, K. Bull. Chem Soc. Jpn. 1982, 55, 2456; Shimizu, T.; Hayashi, Y.; Nakano, M.; Teramura, K. Bull. Chem. Soc. Jpn. 1984, 57, 134; Norman, M. H., Heathcock, C. H. J. Org. Chem 1987, 52, 226; Shimizu, T.; Hayashi, Y.; Miki, M.; Teramura, K. J. Org. Chem. 1987, 52, 2277; Shimizu, T.; Hayashi, Y.; Miki, M.; Teramura, K. J. Heterocycl. Chem. 1990, 27, 1669; Katayama, H.; Takatsu, N.; Kitano, H.; Shimaya, Y. Chem. Pharm. Bull. 1990, 38, 1129. Also see ref. 4c) and 4d).
15. As papers on acid-catalyzed hydrazone-azomethine imine isomerization and its 1,3-dipolar cycloaddiotion reaction: LeFevre, G.; Hamelin, J.; Tetrahedron Lett. 1979, 4503; LeFevre, G.; Sinbandhit, S.; Hamelin, J. Tetrahedron 1979, 35, 1821; LeFevere, G.; Hamelin, J. Tetrahedron 1980, 36, 887; Fouchet, B.; Houch, M.; Hamelin, J. Tetrahedron Lett. 1981, 22, 1333; Shimizu, T.; Hayashi, Y.; Miki, M.; Teramura, K. Bull. Chem Soc. Jpn. 1982, 55, 2456; Shimizu, T.; Hayashi, Y.; Nakano, M.; Teramura, K. Bull. Chem. Soc. Jpn. 1984, 57, 134; Norman, M. H., Heathcock, C. H. J. Org. Chem 1987, 52, 226; Shimizu, T.; Hayashi, Y.; Miki, M.; Teramura, K. J. Org. Chem. 1987, 52, 2277; Shimizu, T.; Hayashi, Y.; Miki, M.; Teramura, K. J. Heterocycl. Chem. 1990, 27, 1669; Katayama, H.; Takatsu, N.; Kitano, H.; Shimaya, Y. Chem. Pharm. Bull. 1990, 38, 1129. Also see ref. 4c) and 4d).
16. As papers on acid-catalyzed hydrazone-azomethine imine isomerization and its 1,3-dipolar cycloaddiotion reaction: LeFevre, G.; Hamelin, J.; Tetrahedron Lett. 1979, 4503; LeFevre, G.; Sinbandhit, S.; Hamelin, J. Tetrahedron 1979, 35, 1821; LeFevere, G.; Hamelin, J. Tetrahedron 1980, 36, 887; Fouchet, B.; Houch, M.; Hamelin, J. Tetrahedron Lett. 1981, 22, 1333; Shimizu, T.; Hayashi, Y.; Miki, M.; Teramura, K. Bull. Chem Soc. Jpn. 1982, 55, 2456; Shimizu, T.; Hayashi, Y.; Nakano, M.; Teramura, K. Bull. Chem. Soc. Jpn. 1984, 57, 134; Norman, M. H., Heathcock, C. H. J. Org. Chem 1987, 52, 226; Shimizu, T.; Hayashi, Y.; Miki, M.; Teramura, K. J. Org. Chem. 1987, 52, 2277; Shimizu, T.; Hayashi, Y.; Miki, M.; Teramura, K. J. Heterocycl. Chem. 1990, 27, 1669; Katayama, H.; Takatsu, N.; Kitano, H.; Shimaya, Y. Chem. Pharm. Bull. 1990, 38, 1129. Also see ref. 4c) and 4d).
17. As papers on acid-catalyzed hydrazone-azomethine imine isomerization and its 1,3-dipolar cycloaddiotion reaction: LeFevre, G.; Hamelin, J.; Tetrahedron Lett. 1979, 4503; LeFevre, G.; Sinbandhit, S.; Hamelin, J. Tetrahedron 1979, 35, 1821; LeFevere, G.; Hamelin, J. Tetrahedron 1980, 36, 887; Fouchet, B.; Houch, M.; Hamelin, J. Tetrahedron Lett. 1981, 22, 1333; Shimizu, T.; Hayashi, Y.; Miki, M.; Teramura, K. Bull. Chem Soc. Jpn. 1982, 55, 2456; Shimizu, T.; Hayashi, Y.; Nakano, M.; Teramura, K. Bull. Chem. Soc. Jpn. 1984, 57, 134; Norman, M. H., Heathcock, C. H. J. Org. Chem 1987, 52, 226; Shimizu, T.; Hayashi, Y.; Miki, M.; Teramura, K. J. Org. Chem. 1987, 52, 2277; Shimizu, T.; Hayashi, Y.; Miki, M.; Teramura, K. J. Heterocycl. Chem. 1990, 27, 1669; Katayama, H.; Takatsu, N.; Kitano, H.; Shimaya, Y. Chem. Pharm. Bull. 1990, 38, 1129. Also see ref. 4c) and 4d).
18. As papers on acid-catalyzed hydrazone-azomethine imine isomerization and its 1,3-dipolar cycloaddiotion reaction: LeFevre, G.; Hamelin, J.; Tetrahedron Lett. 1979, 4503; LeFevre, G.; Sinbandhit, S.; Hamelin, J. Tetrahedron 1979, 35, 1821; LeFevere, G.; Hamelin, J. Tetrahedron 1980, 36, 887; Fouchet, B.; Houch, M.; Hamelin, J. Tetrahedron Lett. 1981, 22, 1333; Shimizu, T.; Hayashi, Y.; Miki, M.; Teramura, K. Bull. Chem Soc. Jpn. 1982, 55, 2456; Shimizu, T.; Hayashi, Y.; Nakano, M.; Teramura, K. Bull. Chem. Soc. Jpn. 1984, 57, 134; Norman, M. H., Heathcock, C. H. J. Org. Chem 1987, 52, 226; Shimizu, T.; Hayashi, Y.; Miki, M.; Teramura, K. J. Org. Chem. 1987, 52, 2277; Shimizu, T.; Hayashi, Y.; Miki, M.; Teramura, K. J. Heterocycl. Chem. 1990, 27, 1669; Katayama, H.; Takatsu, N.; Kitano, H.; Shimaya, Y. Chem. Pharm. Bull. 1990, 38, 1129. Also see ref. 4c) and 4d).
19. As papers on acid-catalyzed hydrazone-azomethine imine isomerization and its 1,3-dipolar cycloaddiotion reaction: LeFevre, G.; Hamelin, J.; Tetrahedron Lett. 1979, 4503; LeFevre, G.; Sinbandhit, S.; Hamelin, J. Tetrahedron 1979, 35, 1821; LeFevere, G.; Hamelin, J. Tetrahedron 1980, 36, 887; Fouchet, B.; Houch, M.; Hamelin, J. Tetrahedron Lett. 1981, 22, 1333; Shimizu, T.; Hayashi, Y.; Miki, M.; Teramura, K. Bull. Chem Soc. Jpn. 1982, 55, 2456; Shimizu, T.; Hayashi, Y.; Nakano, M.; Teramura, K. Bull. Chem. Soc. Jpn. 1984, 57, 134; Norman, M. H., Heathcock, C. H. J. Org. Chem 1987, 52, 226; Shimizu, T.; Hayashi, Y.; Miki, M.; Teramura, K. J. Org. Chem. 1987, 52, 2277; Shimizu, T.; Hayashi, Y.; Miki, M.; Teramura, K. J. Heterocycl. Chem. 1990, 27, 1669; Katayama, H.; Takatsu, N.; Kitano, H.; Shimaya, Y. Chem. Pharm. Bull. 1990, 38, 1129. Also see ref. 4c) and 4d).
20. As papers on acid-catalyzed hydrazone-azomethine imine isomerization and its 1,3-dipolar cycloaddiotion reaction: LeFevre, G.; Hamelin, J.; Tetrahedron Lett. 1979, 4503; LeFevre, G.; Sinbandhit, S.; Hamelin, J. Tetrahedron 1979, 35, 1821; LeFevere, G.; Hamelin, J. Tetrahedron 1980, 36, 887; Fouchet, B.; Houch, M.; Hamelin, J. Tetrahedron Lett. 1981, 22, 1333; Shimizu, T.; Hayashi, Y.; Miki, M.; Teramura, K. Bull. Chem Soc. Jpn. 1982, 55, 2456; Shimizu, T.; Hayashi, Y.; Nakano, M.; Teramura, K. Bull. Chem. Soc. Jpn. 1984, 57, 134; Norman, M. H., Heathcock, C. H. J. Org. Chem 1987, 52, 226; Shimizu, T.; Hayashi, Y.; Miki, M.; Teramura, K. J. Org. Chem. 1987, 52, 2277; Shimizu, T.; Hayashi, Y.; Miki, M.; Teramura, K. J. Heterocycl. Chem. 1990, 27, 1669; Katayama, H.; Takatsu, N.; Kitano, H.; Shimaya, Y. Chem. Pharm. Bull. 1990, 38, 1129. Also see ref. 4c) and 4d).
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22. + + 2] cycloaddition.
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