The Synthesis of Azahomotryptophane Derivatives. The Transformation of N-Trifluoroacetyl-5-bromo-4-oxonorvaline Methyl Ester into 4-(Imidazo[1,2-a]azinyl-3)-4-oxohomoalanine Derivatives

Journal of Heterocyclic Chemistry

Volumn 34, Issue 3, 1997, Pages 853-856

  Škof, Marko ^a   Svete, Jurij ^a   Stanovnik, Branko ^a  

^a UNIVERSITY OF LJUBLJANA   (Slovenia)

Author keywords

[No Author keywords available]

Indexed keywords

TRYPTOPHAN DERIVATIVE;

AMINO ACID SUBSTITUTION; AMINO ACID TRANSPORT; ARTICLE; DERIVATIZATION; DRUG SYNTHESIS; DRUG TRANSFORMATION; NONHUMAN; REACTION ANALYSIS; STRUCTURE ANALYSIS;

EID: 0030831224     PISSN: 0022152X     EISSN: None     Source Type: Journal    
DOI: 10.1002/jhet.5570340323     Document Type: Article

References (10)

1. For a review see: E. W. Petrillo, Jr., and M. A. Ondetti, Med. Res. Rev., 2, 1 (1982).
2. I. Wagner and J. Musso, Angew. Chem., 95, 827 (1983).
3. G. C. Barrett, Synthesis of Amino Acids in Chemistry and Biochemistry of Amino Acids, G. C. Barrett, cd, Chapman and Hall, London, 1985, pp 246-296.
4. For a review see: B. Stanovnik, Methyl 2-Benzoylamino-3-dimethylaminopropenoate in the Synthesis of Heterocyclic Systems, Progress in Heterocyclic Chemistry, Vol 5, H. Suschitzky and E. F. V. Scriven, eds, Pergamon Press, Oxford 1993, pp 34-53.
5. J. Svete, B. Stanovnik, and M. Tišler, J. Heterocyclic Chem., 31, 1259 (1994), and references cited therein.
6. B. Stanovnik, A. Štimac, M. Tišler, and B. Verček, J. Heterocyclic. Chem., 19, 577 (1982), and references cited therein.
7. S. Podergajs, B. Stanovnik, and M. Tišler, Synthesis, 263 (1984).
8. Before trituration with water (see general procedure), the residue was first purified by flash chromatography (silica gel-Kieselgel 60, ethyl acetate as eluent).
9. Reaction was carried out at room temperature (see general procedure).
10. Hot water (20 ml, approximately 80°) was added to the residue which was obtained after evaporation of volatile components (see general procedure). While stirring, this mixture was allowed to cool to room temperature. The precipitate was collected by filtration to give 9.