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

A 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.

Automated summary

A novel bis-heterocyclic system containing 1,2-dihydro-3H-pyrrolo[3,4-b]indolizin-3-one and 1,5-disubstituted tetrazole moieties was designed and synthesized as a Copper (II) recognizing agent. The compounds were prepared using a novel one-pot synthetic strategy involving four-step reactions. The photophysical properties of the obtained compounds were evaluated for their response to Copper (II).