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Aza-Henry and aza-Knoevenagel reactions of nitriles for the synthesis of pyrido[1,2-a]indoles

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Abstract

N-(Propargyl)indole-2-carbonitriles undergo DBU-catalyzed addition of CH-acids to nitriles, followed by cyclization to give 9-aminopyrido[1,2-a]indoles. The reaction proceeds through the initial formation of a push–pull enamine, alkyne–allene rearrangement and intramolecular nucleophilic cyclization. Nitromethane and malonate esters can be employed as the CH-acids. The resulting compounds were found to exhibit fluorescence properties.

Graphical abstract: Aza-Henry and aza-Knoevenagel reactions of nitriles for the synthesis of pyrido[1,2-a]indoles

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Article information


Submitted
03 Mar 2020
Accepted
01 May 2020
First published
01 May 2020

Chem. Commun., 2020, Advance Article
Article type
Communication

Aza-Henry and aza-Knoevenagel reactions of nitriles for the synthesis of pyrido[1,2-a]indoles

R. R. Zalte, A. A. Festa, N. E. Golantsov, K. Subramani, V. B. Rybakov, A. V. Varlamov, R. Luque and L. G. Voskressensky, Chem. Commun., 2020, Advance Article , DOI: 10.1039/D0CC01652G

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