Synthesis of 1,5‐Disubstituted Tetrazole−Indolizine Bis‐Heterocycles and Their Copper (II) Recognizing Properties

Abstract

AbstractA novel bis‐heterocyclic system encompassing the 1,2‐dihydro‐3H‐pyrrolo[3,4‐b]indolizin‐3‐one and 1,5‐disubstituted tetrazole moieties was designed, synthesized, and evaluated as a Copper (II) recognizing agent. This was achieved by exploiting the optical characteristics of indolizine and the copper recognizing activity of tetrazoles. For the preparation of these compounds, a novel and simple synthetic strategy consisting in a double one‐pot process involving four‐step reactions was developed. The first process is a one‐pot five component reaction by using propargylamine as a bifunctional reactant to access the key intermediate, the N‐acylated tetrazole. Consequently, N‐acylated tetrazole was subjected to a one‐pot three component reaction, consisting in a bimolecular nucleophilic substitution followed of a domino process to afford the target compounds. The photophysical properties of the obtained bis‐heterocycles were evaluated against copper (II) addition.