J. Jumina
Jun 15, 2010
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Journal
Indonesian Journal of Chemistry
Abstract
Alkylation of 3-aryl-4,6-dimethoxyindole 3a and 3b with methyl and ethyl -bromoacetates afforded good yields of indol-1-ylacetates 4. Treatment of these indoles 4 with the Vilsmeier formylation reagent gave formylindoles 5 in 54-81 % yield. These formylindole 5 underwent intramolecular aldol condensation when treated with sodium hydride in tetrahydrofuran to give pyrroloindole-4-carboxylates 6 in 30-60 % yield. Structural assignment based on spectroscopic data confirmed the structure of the synthesized pyrroloindoles. In the case of pyrroloindole 6c, the structure of this molecule was also proven by X-ray crystallography data.