Keywords
1,4-dihydropyridines
3(4)-aminoalk-2-enoates
aminomalonate
catalysis
chemoselectivity
Cyclization
Michael addition
pharmacology
propynoates
pyrroles
Abstract
3-(2-Pyrrolyl)propynoates variously substituted in the pyrrole moiety add aminomalonate (excess Cs2CO3, reflux in MeCN, 6 h) to chemoselectively afford either aminoalkyl or alkylamino Michael adducts depending on the reactant ratio. In cases of 3-(1-alkyl-2-pyrrolyl)propynoates and 3-bromopropynoate as the additional co-reactant, 2-(1-alkyl-2- pyrrolyl)-1,4-dihydropyridines were formed.
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