Paper
ALKYLATION OF METHYL 3-HYDROXYINDOLE-2-CARBOXYLATE USE IN PYRIMIDINE SYNTHESIS
Published Jan 1, 1995 · A. Bourlot, J. Mérour
Heterocyclic Communications
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Abstract
Three alkylation sites (O.C-2 or Ν atoms) are present on methyl 3-hydroxyindole-2-carboxylate 4a. Functionalized halides were used to study the regioselectivity of these alkylations. In order to illustrate this work, the pyrimidine 17 has been synthesized from the O-alkylated compound 13a. Introduction : 3-Hydroxyindole-2-carboxylic acid derivatives 1 represent well-known and readily available compounds (1). Compounds 1 are used as synthons for the preparation of indole-fused heterocycles, incorporating the 3hydroxy group in ring formation to give compounds of potential medicinal interest, e.g. 2 (anti-allergy and/or CNS activities) (2,3). Recently, Hirota et at. reported that some 4-alkylamino-6,7-dihydro-5H-pyrimido[5,4-c(][1]benzazepines 3a or 5,6-dihydro[1]benzoxepino[5,4-c(jpyrimidin-4(3H)-one 3b (6) show stronger inhibitory activity against collagen-induced aggregation of rabbit blood platelets than aspirin, which is an anti-platelet agent (6,7). Our goal was to replace the benzo part of compound 3b by an indole moiety.
This study demonstrates that methyl 3-hydroxyindole-2-carboxylate can be alkylated to produce pyrimidines with potential medicinal interest, such as anti-allergy and CNS activities.
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