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

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.