Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2022, Issue 34, Pages -Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.202200230
Keywords
Copper recognition; Heterocycles; Multicomponent reactions; Supramolecular chemistry; Ugi-azide
Categories
Funding
- CONACYT [619466/819169]
- CIC-UMSNH
- CIC-UMSNH, Mexico [14646]
- Programa para el Desarrollo Profesional Docente, tipo superior, PRODEP [PTC-404]
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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).
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.
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