A NOVEL APPROACH TO THE 5YNTНESIS OF 3-АСYL SUBSTITUTED INDOLIZINES. THE SYNTHESIS OF 3-(INDOLIZINYL-2)ALANINE- АND 4-(INDOLIZINУL-3)НOМОАLАNINЕ DERIVATIVES

Authors

  • Lucija Jukić Faculty of Chemistry and Chemical Technology, University of Ljubljana, Ljubljana
  • Urška Bratušek Faculty of Chemistry and Chemical Technology, University of Ljubljana, Ljubljana
  • Marko Škof Faculty of Chemistry and Chemical Technology, University of Ljubljana, Ljubljana
  • Jurij Svete Faculty of Chemistry and Chemical Technology, University of Ljubljana, Ljubljana
  • Branko Stanovnik Faculty of Chemistry and Chemical Technology, University of Ljubljana, Ljubljana

Abstract

А novel approach to the synthesis of 3-aсуlindolizines and the transformations of some hetarylacetic acids into tryptophane analogues are described. Reaction of ethyl 2-pyridinylacetate and methyl 2-quinolinylаcetаte with N-tгifluoroaсetyl-5-brоmо-4-охonоrvaline methyl ester led to N-trifluoroаcetyl-3-(1-ethоxусarbonylindolizinуl-2)alаninе
methyl ester and N-tгifluoroacetуl-3-(3-methoхyсarbonуlpуrrolo[1,2-а]quinolinyl-2)-alanine methyl ester, respectively. Treatment of ethyl 2 -pугidinуlaсetаte and 2-pyridinylacetonitrile, first with N,N-dimethylformamide dimethyl acetal (DMFDMA) followed by reaction with phenacyl bromide, gave the corresponding 3-bеnzоуlindoliziпеs, while the reaction of ethyl 2-pyridinуlaсetate and 2-pyridinylaсetоnitгile with DMFDMA, followed by treatment with (S)-N-trifluoгoаcetуl-5-bromo-4-охonorvaline methyl ester, gave the corresponding N-trifluoroaсetyl-4-oхo-4-(indolizinyl-3)homoalаnine methyl
esters.

How to Cite
Jukić, L.; Bratušek, U.; Škof, M.; Svete, J.; Stanovnik, B. Chem. Heterocycl. Compd. 1996, 32, 1295. [Khim. Geterotsikl. Soedin. 1996, 1510.]

For this article in the English edition, see DOI https://doi.org/10.1007/BF01169960

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Published

1996-11-24

Issue

No. 11/12 (1996)

Section

Original Papers