Huisgen Cycloaddition Reaction of Nitrile Imines With Acyl Phosphonates: Synthesis of Phosphonate Containing 1,3,4-Oxadiazoles and DFT Analysis

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dc.contributor.authorPolat-Cakir, Sidika
dc.contributor.authorAltinisik, Sinem
dc.date.accessioned2026-02-03T12:03:18Z
dc.date.available2026-02-03T12:03:18Z
dc.date.issued2025
dc.departmentÇanakkale Onsekiz Mart Üniversitesi
dc.description.abstractThe application of the Huisgen cycloaddition reaction between acyl phosphonates (dipolarophile) and highly reactive intermediate nitrile imines (NI) as a 1,3-dipole in situ generated by the conversion of hydrazonyl chlorides in the presence of a base is reported to synthesize the phosphonate-containing 1,3,4-oxadiazole compounds in 53%-89% yields. Oxadiazole compounds stand out as significant target molecules in drug design and development due to their potential biological activities. Having a phosphonate group in the structure of the 1,3,4-oxadiazole may enhance biological activity be enhanced. We have synthesized 10 new phosphonate-containing oxadiazole compounds that are fully characterized by using spectroscopic analysis. Density Functional Theory (DFT) calculations were carried out to compare the energies of the frontier orbitals of the acyl phosphonates (dipolarophile) and NI (1,3 dipole) to determine the nature of the interaction between the dipolarophile and the 1,3-dipole. The relevant Huisgen cycloaddition reaction proceeds via a normal-electron demand (NED) pathway.
dc.description.sponsorshipTrkiye Bilimsel ve Teknolojik Arascedil;timath;rma Kurumu
dc.description.sponsorshipThis work was supported by the Scientific Research Commission of Canakkale Onsekiz Mart University under project number FBA-2023-4335. Additionally, the supplementary budget for this project was provided by TUBITAK 1002-B under project number 124Z310. Both financial supports were appreciated.
dc.identifier.doi10.1002/jhet.70067
dc.identifier.endpage1628
dc.identifier.issn0022-152X
dc.identifier.issn1943-5193
dc.identifier.issue11
dc.identifier.scopus2-s2.0-105014953444
dc.identifier.scopusqualityQ2
dc.identifier.startpage1620
dc.identifier.urihttps://doi.org/10.1002/jhet.70067
dc.identifier.urihttps://hdl.handle.net/20.500.12428/35004
dc.identifier.volume62
dc.identifier.wosWOS:001564091900001
dc.identifier.wosqualityQ2
dc.indekslendigikaynakWeb of Science
dc.indekslendigikaynakScopus
dc.language.isoen
dc.publisherWiley
dc.relation.ispartofJournal of Heterocyclic Chemistry
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanı
dc.rightsinfo:eu-repo/semantics/closedAccess
dc.snmzKA_WOS_20260130
dc.subjectacyl phosphonates
dc.subjectDFT
dc.subjectHuisgen cycloaddition
dc.subjectnitrile imines
dc.subjectoxadiazole
dc.titleHuisgen Cycloaddition Reaction of Nitrile Imines With Acyl Phosphonates: Synthesis of Phosphonate Containing 1,3,4-Oxadiazoles and DFT Analysis
dc.typeArticle

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