Pseudo-Five-Component Condensation for the Diversity-Oriented Synthesis of Novel Indoles and Quinolines Containing Pseudo-Peptides (Tricarboxamides)

Document Type: Research Article

Authors

1 Department of Chemistry, Faculty of Science, Alzahra University, Tehran, I.R. IRAN

2 School of Chemistry and Physics, University of KwaZulu-Natal, Private Bag X54001, Durban, 4000, SOUTH AFRICA

Abstract

A novel series of indole and quinoline tricarboxamides were synthesized using simple and efficient one-pot pseudo-five-component reactions of 2-formylindole or 2-chloro-3-formyl quinolines, isocyanides, amines, and Meldrum’s acid as a CH-acid in CH2Cl2 at room temperature. This conversion has been achieved via the construction of new bonds including two C-C bonds, two C-N bonds, and one C=O bond. Remarkably, three peptide bonds were formed through a domino sequence including Knoevenagel reaction, [1+4] cycloaddition, deacetonation and also, aminolysis reaction. Particularly, a number of structurally remarkable and pharmacologically significant products were provided in excellent yields.

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Main Subjects


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