Tytuł artykułu
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Języki publikacji
Abstrakty
A practical procedure for synthesis of 6-aminoazulene (3) via Vicarious Nucleophilic Substitution of Hydrogen (VNS) amination of azulene with 4-amino-1,2,4-triazole is reported. Amination with use of N,N,N-trimethylhydrazinium iodide (TMHI) of more electrophilic azulene derivatives, substituted at position 1- with CN or COPh group, afforded a mixture of 4-, 6-, and 8-aminoazulenes. Attempts to convert 6-aminoazulene (3) into diazonium salt failed, only formation of small quantities of the "auto-coupling" product, 1-(azulen-6-ylazo)-azulen-6-yl-amine, was observed.
Wydawca
Czasopismo
Rocznik
Tom
Strony
275--281
Opis fizyczny
Bibliogr. 18 poz., rys.
Twórcy
autor
- Institute of Organic Chemistry, Polish Academy of Sciences, ul. Kasprzaka 44/52, PL-01-224 Warszawa, Poland
autor
- Institute of Organic Chemistry, Polish Academy of Sciences, ul. Kasprzaka 44/52, PL-01-224 Warszawa, Poland
autor
- Institute of Organic Chemistry, Polish Academy of Sciences, ul. Kasprzaka 44/52, PL-01-224 Warszawa, Poland
Bibliografia
- 1. Anderson Jr. A. G., Gale D. J., McDonald R. N., Andreson R.G. and Rhodes R .C., J. Org. Chem.,29,1373 (1964).
- 2. Mąkosza M. and Wojciechowski K., Liebigs Ann./Recueil., 1805 (1997).
- 3. a) Podraża R., PhD Thesis, Institute of Organic Chemistry, Polish Academy of Sciences, Warszawa, 1998. b) Mąkosza M. and Podraża R., Eur. J. Org. Chem., 193 (2000).
- 4. Mąkosza M. and Białecki M., J. Org. Chem., 63, 4878 (1998).
- 5. Seko S. and Kawamura N., J. Org. Chem., 61,442 (1996).
- 6. Pagoria P.F., Mitchell A.R. and Schmidt R.D., J. Org. Chem., 61, 2934 (1996).
- 7. Katritzky A.R. and Laurenzo K.S., J. Org. Chem., 51, 5039 (1986); 53, 3978 (1988).
- 8. Suwiński J., Świerczek K. and Glowiak T., Tetrahedron, 49, 5339 (1993).
- 9. Mąkosza M. and Staliński K., Chem. Eur. J., 3, 2025 (1997).
- 10. Nozoe T., Seto S., Matsumura S. and Murase Y., Bull. Chem. Soc. Jpn, 35, 1179 (1962).
- 11. Nozoe T., Takase K. and Tada M., Bull. Chem. Soc. Jpn, 36, 1006(1963).
- 12. Le V.P. and Wells P.R., Aust.J. Chem., 50, 1119 (1997).
- 13. McDonald R.N. and Richmond I. M., J. Chem. Soc., Chem. Commun., 605 (1973).
- 14. Kazennova N.B., Kazitsyna L.A. and Nefedov V.A., Zh. Org. Khim., 14, 1117 (1978).
- 15. Kon H., Science Repts. Töhoku Univ., First Ser., 38, 67 (1954); CA, 49: 10046e (1955).
- 16. Lacroix P.G., Molfant I., Iftime G., Razus A.C., Nakatani K. and Delaire J.A., Chem. Eur. 7, 6, 2599 (2000).
- 17. a) Cadogan J.I.G. and Molina G.A.,7 Chem. Soc., Perkin Trans. 1,541 (1973). b) Doyle M.P., Dellaria Jr. J.F., Siegfried B. and Bishop S.W., J. Org. Chem., 42, 3494 (1977).
- 18. Vogel A.I., A Text-Book of Practical Organic Chemistry Including Qualitative Organic Analysis, Longmans Green, NY, 1956.
Typ dokumentu
Bibliografia
Identyfikator YADDA
bwmeta1.element.baztech-article-BUJ1-0016-0080