Synthesis of novel hybrid 1,5-disusbtituted 1H-tetrazol-5yl 4,5-dihydro [1,2,3]triazolo[1,5-a]pyrazin-6-ones via high-order MCR-S_N2/intramolecular [3 + 2] cycloaddition sequence

Abstract

A facile and rapid synthesis of a family of new hybrid system 1,5-disusbtituted 1H-tetrazol-5yl 4,5-dihydro [1,2,3]triazolo[1,5-a]pyrazin-6-ones in moderate yields is described. Compounds were synthetized by a high-order multicomponent reaction (MCR) to give N-acylated 1,5-disubstituted tetrazoles followed, without chromatographic purification, by an S_N2/intramolecular [3 + 2] cycloaddition sequence. The target molecules could be useful in drug discovery processes because they contain two very important pharmacophoric moieties: 1,5-disubstituted tetrazole and 1,2,3- triazole.

Graphical Abstract

Keywords:

• Fused triazoles
• high-order multicomponent reaction
• hybrids compounds
• intramolecular azide-alkyne cycloaddition
• tetrazoles

Acknowledgments

C.M. A-M. (756225) and G. S-G. (772950) acknowledges the support of CONACYT through a graduate scholarship. All authors are grateful for financial support from Programa para el Desarrollo Profesional Docente, para el Tipo Superior (PRODEP PTC-404) and CIC-UMSNH (14766), as well as Ph.D student Josue Valentin Escalera for English support.

Disclosure statement

No potential conflict of interest was reported by the author(s).

Additional information

Funding

This work was supported by Programa para el Desarrollo Profesional Docente, para el Tipo Superior [PRODEP PTC-404] and CIC-UMSNH (14766).