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dc.contributor.authorSari, Ozlem
dc.contributor.authorSeybek, Ali Fatih
dc.contributor.authorKaya, Serdal
dc.contributor.authorMenges, Nurettin
dc.contributor.authorErdem, Safiye Sag
dc.contributor.authorBalci, Metin
dc.date.accessioned2019-11-24T20:38:07Z
dc.date.available2019-11-24T20:38:07Z
dc.date.issued2019
dc.identifier.issn1434-193X
dc.identifier.issn1099-0690
dc.identifier.urihttps://dx.doi.org/10.1002/ejoc.201900084
dc.identifier.urihttps://hdl.handle.net/20.500.12513/2475
dc.descriptionWOS: 000483709700031en_US
dc.description.abstractThe reaction of pyrrole- and indole-carbaldehydes having a propargyl group attached to the nitrogen atom with various amines was studied. The reaction with ammonia formed pyrrolo[1,2-a]pyrazine and pyrazino[1,2-a]indole while the reaction with alkylamines such as methyl, ethyl, hexyl, and benzylamines formed the corresponding pyrazinone derivatives. Unexpectedly, the reaction with allylamine and propargylamine formed pyrazine derivatives in which the allyl and propargyl groups were removed from the molecule. On the other hand, the reaction of N-propargylated pyrrole-carbaldehyde formed indolizine derivatives upon reaction with sterically bulky adamantyl- and tert-butylamines. To understand the main factors causing these differences in reactivity, the reaction mechanisms were studied by means of computational methods. Our calculations showed that bulky amines tend to attack the central carbon of allene formed by the isomerization of N-propargyl functionality, while the attack on the carbonyl carbon by aliphatic amines is more profound.en_US
dc.language.isoengen_US
dc.publisherWILEY-V C H VERLAG GMBHen_US
dc.relation.isversionof10.1002/ejoc.201900084en_US
dc.rightsinfo:eu-repo/semantics/openAccessen_US
dc.subjectPyrrolo[1en_US
dc.subject2-a]pyrazineen_US
dc.subjectAllenesen_US
dc.subjectIminesen_US
dc.subjectDensity functional calculationsen_US
dc.subjectReaction mechanismsen_US
dc.titleMechanistic Insights into the Reaction of N-Propargylated Pyrrole- and Indole-Carbaldehyde with Ammonia, Alkyl Amines, and Branched Amines: A Synthetic and Theoretical Investigationen_US
dc.typearticleen_US
dc.relation.journalEUROPEAN JOURNAL OF ORGANIC CHEMISTRYen_US
dc.contributor.departmentKırşehir Ahi Evran Üniversitesi, Fen-Edebiyat Fakültesi, Kimya Bölümüen_US
dc.identifier.volume2019en_US
dc.identifier.issue31-32en_US
dc.identifier.startpage5261en_US
dc.identifier.endpage5274en_US
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanıen_US


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