Novel method for synthesis of aryl hydrazones from α-diazo esters: scope and limitations of nucleophiles

Tetrahedron

Volumn 65, Issue 2, 2009, Pages 461-468

  Yasui, Eiko ^a   Wada, Masao ^a   Takamura, Norio ^a  

^a MUSASHINO UNIVERSITY   (Japan)

Author keywords

Diazo ester; Fischer indole synthesis; Hydrazone

Indexed keywords

ALCOHOL; ALPHA DIAZO ESTER DERIVATIVE; ARYL HYDRAZONE DERIVATIVE; BROMINE DERIVATIVE; CHLORIDE; ESTER DERIVATIVE; GRIGNARD REAGENT; HYDRAZONE DERIVATIVE; INDOLE DERIVATIVE; PYRIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; COLUMN CHROMATOGRAPHY; CYCLIZATION; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; SYNTHESIS;

EID: 56949099032     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.11.028     Document Type: Article

References (20)

1. Gribble G.W. J. Chem. Soc., Perkin Trans. 1 (2000) 1045-1075
2. Gilchrist T.L. J. Chem. Soc., Perkin Trans. 1 (2001) 2491-2515
3. Fischer E., and Jourdan F. Ber. 16 (1883) 2241-2245
4. Fischer E., and Hess O. Ber. 17 (1884) 559-568
5. Yasui E., Wada M., and Takamura N. Tetrahedron Lett. 47 (2006) 743-746
6. Yasui E., Wada M., and Takamura N. Chem. Pharm. Bull. 55 (2007) 1652-1654
7. Arata Y., Sakai M., and Yasuda S. Chem. Pharm. Bull. 20 (1972) 1745-1751
8. Przheval'skii N.M., Skvortsova N.S., and Magedov I.V. Chem. Heterocycl. Compd. 38 (2002) 1055-1061
9. Przheval'skii N.M., Skvortsova N.S., and Magedov I.V. Chem. Heterocycl. Compd. 39 (2003) 161-167
10. syn-Fydrazone 2a′ was prepared by heating anti-hydrazone 2a with DBU in toluene at 120 °C in a sealed tube. Most of 2a isomerized to 2a′ in 2 h and 2a′ was isolated in 75% yield.
11. Takamura N., Mizoguchi T., Koga K., and Yamada S. Tetrahedron Lett. 12 (1971) 4495-4498
12. Takamura N., Mizoguchi T., Koga K., and Yamada S. Tetrahedron 31 (1975) 227-230
13. Although the relative positions of the substituents of 2g are the same as those of other hydrazones, its configuration is syn because sulfur atom has higher priority than oxygen.
14. Maddirala S.J., Gokak V.S., Rajur S.B., and Basanagoudar L.D. Tetrahedron Lett. 44 (2003) 5665-5668
15. Phillips J.E., and Herber R.H. J. Organomet. Chem. 268 (1984) 39-47
16. Gaus P.L., Haim A., and Johnson F. J. Org. Chem. 42 (1977) 564-565
17. Gilman H., and Spatz S.M. J. Org. Chem. 16 (1951) 1485-1494
18. Song J.J., Reeves J.T., Gallou F., Tan Z., Yee N.K., and Senanayake C.H. Chem. Soc. Rev. 36 (2007) 1120-1132
19. Novel compounds are listed as follows: 2c, 2d, 2f, 2g, 2h, 3c, 3d, 3f, 3g, 4a, 4c, 4d, 4e, 4f, 4g, 5c, 5d, 5f, 5g, 6a, 6c, 6d, 7a, 8a, 8b, 8c, 8d, 9a, 9b, 9c, 9d, 10b, 10c, 10d, 11, and 12.
20. Gault H., and Weick R. Bull. Soc. Chim. Fr. 4 (1922) 867-892