Facile preparation of hydrazones by the treatment of azides with hydrazines catalyzed by FeCl3·6H2O

Journal of Organic Chemistry

Volumn 65, Issue 19, 2000, Pages 6268-6269

  Barrett, Ian C ^b   Langille, Jonathan D ^a,b   Kerr, Michael A ^b  

^a GENZYME CORPORATION   (United States)

^b UNIVERSITY OF WESTERN ONTARIO   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

AZIDE; HYDRAZINE DERIVATIVE; HYDRAZONE DERIVATIVE;

CHEMICAL ANALYSIS; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; NOTE; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0034703196     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo000708w     Document Type: Note

References (17)

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3. (b) Kamal, A.; Reddy, B. S. N.; Reddy, B. S. P. Bioorg. Med. Chem. Lett. 1997, 7, 1825-1828.
4. There are differences between our optimized reaction conditions and those of Kamal (acetonitrile rather than methanol as solvent, the presence of charcoal in their case). However, using the exact conditions (and substrates) of Kamal, we observed no reduction to the amines. The substrates remained unchanged for the most part; however, phenyl azide produced a small amount of aniline along with several other unidentified products when reacted for prolonged periods. While we do not dispute the findings of Kamal, we can offer no explanation at this time for this discrepancy.
5. Wuts, P. G. M.; Greene, T. W. Protective Groups in Organic Synthesis; Wiley: New York, 1991.
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8. 13C NMR, and MS). In addition, several hydrazones (Table 1, entries 1 and 11) were synthesized for comparison from the aldehydes using known procedures.
9. For published data on the N,N-dimethylhydrazones in Table 1, see: (a) (benzaldehyde, cinnamaldehyde, acetophenone) Sharma, S. D.; Pandhi, S. B. J. Org. Chem. 1990, 55, 2196-2200.
10. (b) (p-bromobenzaldehyde) Said, S. B.; Skarzewski, J. M.; Mlochowski, J. Synthesis 1989, 223-224.
11. (c) (p-nitrobenzaldehyde, phenylacetaldehyde) Clark, L. F.; O'Sullivan, F.; Hegarty, A. F. J. Chem. Soc., Perkin Trans. 2 1991, 1649-1652.
12. (d) (p-methoxybenzaldehyde) Smith, R. F., Albright, J. A.; Waring, A. M. J. Org. Chem. 1966, 31, 4100-4102.
13. (e) (m-methoxybenzaldehyde) Hwu, J. R.; Wang, N. Tetrahedron 1988, 44, 4181-4196.
14. (f) (o-methoxybenzaldehyde, octanal) Wiley, R. H.; Slaymaker, S. C.; Kraus, H. J. Org. Chem. 1957, 22, 204-207.
15. (g) (2-octanone) Yamashita, M.; Matsumiya, K.; Hiroko, M.; Rikisaku, S. Bull. Chem. Soc. Jpn. 1989, 62, 1668-1670.
16. At this time we offer this only as a plausible explanation. We are currently exploring ways to elucidate the mechanistic nature of this reaction.
17. Robinson, B. The Fischer Indole Synthesis; John Wiley and Sons: Chichester, 1982.