Efficient and novel one-pot synthesis of hybridized pyrroles linked to indene in water
Subject Areas : شیمی آلیAtieh Rezvanian 1 , Zahra Albughobeish 2
1 - Assistant Professor
2 - Department of Organic Chemistry, Faculty of Chemistry, Alzahra University, Tehran, Iran
Keywords: Green chemistry, hybrid organic compounds, pyrrole-indene, ninhydrin, enamine.,
Abstract :
In this research, a new method for the synthesis of hybrid indene-pyrroles molecules is presented with high efficiency by taking advantages of the multicomponent reactions, such as the simplicity of the reaction method, the use of less solvent, and shorter reaction time. In this method, there is no need to separate any intermediates. The one-pot four-component reaction between ninhydrin, acetophenone, first-type amine and ethyl acetoacetate in water solvent at 60 °C in the presence of sodium hydroxide led to the synthesis of indene-pyrrole hybrid molecules. In this way, an electrophilic intermediate was created from the reaction of ninhydrin with acetophenone in the playing medium. Then, an enamine intermediate was formed by performing a condensation reaction between the first type amine and ethyl acetoacetate. Next, with the nucleophilic attack and Michael increase of the enamino intermediate to the electrophilic intermediate and then the intramolecular nucleophilic attack of the amine group on the carbonyl ketone, a pyrrole ring was formed. Finally, the indene-pyrrole hybrid derivative was obtained by removing water
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