This review presents the use of α-alkyl- and α-alkoxy-halogenoacetamides as powerful partners for domino and 1,3-dipolar cycloaddition reactions resulting in a ring closure.
A new strategy for the construction of 3-phenyl-1H-pyrrolo-imidazo[1,2-a]pyridine backbone is described. The reaction starts from the coupling between N-tosylhydrazones (NTH) and 2chloro-3-nitroimidazo[1,2-a]pyridines leading to the formation of 3-nitro-2-(arylvinyl)imidazo[1,2-a]pyridine derivatives. Optimization of Cadogan-reductive conditions allowed us the conversion of the obtained nitro derivative to a new scaffold of type 3-aryl-1Hpyrroloimidazo[1,2-a]pyridine. This method provides rapid access to new libraries in the context of diversity-oriented synthesis (DOS) which intends to generate small molecules with a large structure diversity in an efficient manner. Screening of the biological activity of the newly generated compounds leads to the identification of a new hit 5cc which exhibits good antiproliferative activity in submicromolar range against human colon cancer cell line.
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