SYNTHESIS AND TRANSFORMATIONS OF ETHYL (<i>Z</i>)-2-(2,3-DIHYDRO-1,3-DIOXO-1H-ISOINDOL-2-YL)-3-(DIMETHYLAMINO)PROPENOATE

Authors

  • D. Bevk Faculty of Chemistry and Chemical Technology, University of Ljubljana, P.O.B. 537, Askerceva 5, 1001 Ljubljana
  • M. Kmetič Faculty of Chemistry and Chemical Technology, University of Ljubljana, P.O.B. 537, Askerceva 5, 1001 Ljubljana
  • S. Rečnik Faculty of Chemistry and Chemical Technology, University of Ljubljana, P.O.B. 537, Askerceva 5, 1001 Ljubljana
  • J. Svete Faculty of Chemistry and Chemical Technology, University of Ljubljana, P.O.B. 537, Askerceva 5, 1001 Ljubljana
  • L. Golič Faculty of Chemistry and Chemical Technology, University of Ljubljana, P.O.B. 537, Askerceva 5, 1001 Ljubljana
  • А. Golobič Faculty of Chemistry and Chemical Technology, University of Ljubljana, P.O.B. 537, Askerceva 5, 1001 Ljubljana
  • B. Stanovnik Faculty of Chemistry and Chemical Technology, University of Ljubljana, P.O.B. 537, Askerceva 5, 1001 Ljubljana

Keywords:

amines, enaminones, isoindole, pyranones, pyrimidinones, quinolizinones, cyclizations

Abstract

Ethyl (2)-2-(2,3-dihydrо-1,3-dioxo-1H-isoindol-2-уl)-3-(dimethylamino)propе-noate was prepared in one step from ethyl (2,3-dihydro-1,3-dioxо-1Н-isоindol-2-yl)acetate and bis(dimethylamino)-tert-butoxymethane and treated with various amines and hydrazines to afford the corresponding amino substituted products. Reactions of titled compound with N,N'-, C,N-, and C,O'-ambident nucleophiles in refluxing acetic acid furnished corresponding fused pyrimidinones, quinoli-zinones, and pyranones.

How to Cite
Bevk, D.; Kmetič, M.; Rečnik,S.; Svete, J.; Golič, L.; Golobič, А.; Stanovnik, B. Chem. Heterocycl. Compd. 2001, 37, 1498. [Khim. Geterotsikl. Soedin. 2001, 1651.]

For this article in the English edition, see DOI https://doi.org/10.1023/A:1014505209422

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Published

2001-12-25

Issue

No. 12 (2001)

Section

Original Papers