Structural, electronic, and spectroscopic study on 1,5-methanoazocino[4,3-b]indole synthesized by TFB-based route

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dc.authorid0000-0001-7649-9168
dc.authorscopusid36447801100
dc.authorscopusid6507868758
dc.contributor.authorSerdaroğlu, Goncagül
dc.contributor.authorUludağ, Nesimi
dc.date.accessioned2022-05-11T14:31:06Z
dc.date.available2022-05-11T14:31:06Z
dc.date.issued2021
dc.departmentFakülteler, Fen Edebiyat Fakültesi, Kimya Bölümü
dc.description.abstractThis work proposed a new route to synthesizing pharmaceutical important molecules just in three steps. This synthetic route provides an economical way for synthetic chemistry to get the key products concerning the biochemical importance economically including the monoterpene alkaloids, uleine, tubifolidine. This route involves ring closure and the reaction also involved a cyclization reaction tetrahydrocarbazole with an amine side chain at the C-2 position, and this cyclization was mediated by tetrafluoro-1,4-benzoquinone (TFB). In proposed TFB-based route, (4) (2-(2,3,4,9-tetrahydro-1H-carbazol-2-yl)ethan-1-amine), (5) 2,3,4,5,6,7-hexahydro-1H-1,5-methanoazocino[4,3-b]indole, (6) methyl (1R,5S)-1,3,4,5,6,7-hexahydro-2H-1,5-methanoazocino[4,3-b]indole-2-carboxylate, (7) methyl (1R,5S)-6-oxo-1,3,4,5,6,7-hexahydro-2H-1,5-methanoazocino[4,3-b]indole-2-carboxylate compounds were synthesized and characterized by FTIR and NMR (H-1 and C-13) spectroscopic tools. Besides, the essential intramolecular interactions, chemical reactivity behavior, and the optical property of (7) as a final production of this work have been investigated by NBO, FMO, and NLO analyses, respectively, and the theoretical calculations were performed by both the B3LYP and M06-HF at 6-311 + G(d,p) basis set.
dc.description.sponsorshipScientific and Technological Research Council of Turkey (TUBITAK)Turkiye Bilimsel ve Teknolojik Arastirma Kurumu (TUBITAK) [112T503]; Sivas Cumhuriyet University, Scientific Research Projects Department [CUBAP: EGT-090]
dc.description.sponsorshipThis work was supported by the Scientific and Technological Research Council of Turkey (TUBITAK, Project No.112T503); Sivas Cumhuriyet University, Scientific Research Projects Department (Grant Number: CUBAP: EGT-090) for financial support. All calculations have been carried out at TUBITAK ULAKBIM, High Performance and Grid Computing Center (TR-Grid e-Infrastructure).
dc.identifier.doi10.1007/s11696-021-01683-y
dc.identifier.endpage4564
dc.identifier.issn2585-7290
dc.identifier.issn1336-9075
dc.identifier.issue9en_US
dc.identifier.scopus2-s2.0-85105536194
dc.identifier.scopusqualityQ2
dc.identifier.startpage4549
dc.identifier.urihttps://doi.org/10.1007/s11696-021-01683-y
dc.identifier.urihttps://hdl.handle.net/20.500.11776/7316
dc.identifier.volume75
dc.identifier.wosWOS:000647920100003
dc.identifier.wosqualityQ3
dc.indekslendigikaynakWeb of Science
dc.indekslendigikaynakScopus
dc.institutionauthorUludağ, Nesimi
dc.language.isoen
dc.publisherSpringer International Publishing Ag
dc.relation.ispartofChemical Papers
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanıen_US
dc.rightsinfo:eu-repo/semantics/closedAccess
dc.subject1
dc.subject5-Methanoazocino[4
dc.subject3-b]indole
dc.subjectDasycarpidone
dc.subjectDFT calculation
dc.subjectNBO
dc.subjectFMO
dc.subjectStrychnos-Nux-Vomica
dc.subjectFt-Ir
dc.subjectMolecular-Structure
dc.subjectWave-Functions
dc.subjectNmr
dc.subjectNbo
dc.subjectAlkaloids
dc.subjectNlo
dc.subjectFramework
dc.subjectFmo
dc.titleStructural, electronic, and spectroscopic study on 1,5-methanoazocino[4,3-b]indole synthesized by TFB-based route
dc.typeArticle

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