Nucleophilic and electrophilic cyclization of N-alkyne-substituted pyrrole derivatives: Synthesis of pyrrolopyrazinone, pyrrolotriazinone, and pyrrolooxazinone moieties

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dc.authorid0000-0002-6311-1918
dc.contributor.authorYenice, Işıl
dc.contributor.authorBaşçeken, Sinan
dc.contributor.authorBalcı, Metin
dc.date.accessioned2019-05-13T09:07:12Z
dc.date.available2019-05-13T09:07:12Z
dc.date.issued2017
dc.departmentHitit Üniversitesi, Fen Edebiyat Fakültesi, Kimya Bölümü
dc.description.abstractIntramolecular nucleophilic and electrophilic cyclization of N-alkyne-substituted pyrrole esters is described. Efficient routes towards the synthesis of pyrrolopyrazinone, pyrrolotriazinone and pyrrolooxazinone have been developed. First, N-alkyne-substituted pyrrole ester derivatives were synthesized. Introduction of various substituents into the alkyne functionality was accomplished by a copper-catalyzed cross-coupling reaction. Nucleophilic cyclization of N-alkyne-substituted methyl 1H-pyrrole-2-carboxylates with hydrazine afforded the 6-exo-dig/6-endo-dig cyclization products depending on the electronic nature of the substituents attached to the alkyne. On the other hand, cyclization of N-alkyne-substituted methyl 1H-pyrrole-2-carboxylates with iodine only resulted in the formation of the 6-endo-dig cyclization product regardless of the substitution of the alkyne functionality. © 2017 Yenice et al.
dc.identifier.citationYenice, I., Başçeken, S., Balcı, M. (2017). Nucleophilic and electrophilic cyclization of N-alkyne-substituted pyrrole derivatives: Synthesis of pyrrolopyrazinone, pyrrolotriazinone, and pyrrolooxazinone moieties. Beilstein Journal of Organic Chemistry, 13, 825-834.
dc.identifier.doi10.3762/bjoc.13.83
dc.identifier.endpage834en_US
dc.identifier.issn1860-5397
dc.identifier.scopusqualityQ2
dc.identifier.startpage825en_US
dc.identifier.urihttps://doi.org/10.3762/bjoc.13.83
dc.identifier.urihttps://hdl.handle.net/11491/1746
dc.identifier.volume13en_US
dc.identifier.wosqualityN/A
dc.indekslendigikaynakWeb of Science
dc.indekslendigikaynakScopus
dc.indekslendigikaynakPubMed
dc.language.isoen
dc.publisherBeilstein-Institut Zur Forderung der Chemischen Wissenschaften
dc.relation.ispartofBeilstein Journal of Organic Chemistry
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanı
dc.rightsAttribution 4.0 International (CC BY 4.0)*
dc.rightsinfo:eu-repo/semantics/openAccess
dc.rights.urihttps://creativecommons.org/licenses/by/4.0/*
dc.subjectAlkyne Cyclizationen_US
dc.subjectPyrroleen_US
dc.subjectPyrrolooxazinoneen_US
dc.subjectPyrrolopyrazinoneen_US
dc.subjectPyrrolotriazinoneen_US
dc.titleNucleophilic and electrophilic cyclization of N-alkyne-substituted pyrrole derivatives: Synthesis of pyrrolopyrazinone, pyrrolotriazinone, and pyrrolooxazinone moieties
dc.typeArticle

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