New route for synthesis of 2-(2,2-dimethoxyethyl)-1,2,3,4,5,6-hexahydro-1,5-methanoazocino[4,3-b] indole and DFT investigation

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dc.authorscopusid6507868758
dc.authorscopusid36447801100
dc.authorwosidSerdaroğlu, Goncagül/I-6780-2016
dc.contributor.authorUludağ, Nesimi
dc.contributor.authorSerdaroğlu, Goncagül
dc.date.accessioned2022-05-11T14:31:04Z
dc.date.available2022-05-11T14:31:04Z
dc.date.issued2020
dc.departmentFakülteler, Fen Edebiyat Fakültesi, Kimya Bölümü
dc.description.abstractDevelopment of efficient sequences for the synthesis of the title compound (2-(2,2-dimethoxyethyl)-1,2,3,4,5,6-hexahydro-1,5-methanoazocino[4,3-b]indole) (7) was described. The title compound was synthesized through several steps starting from phenylhydrazine hydrochloride and dimethyl (R)-2-(3-oxocyclohexyl)malonate. In this route, all synthesized compounds were observed by spectroscopic tools (FT-IR, NMR): Methyl-2-(2,3,4,9-1H-carbazol-2-yl)acetate (3), 2-(2,3,4,9-tetrahydro-1H-carbazol-2-yl)acetic acid (4), N-(2,2-dimedioxyethyl)-2-(2,3,4,9-tetrahydro-1H-carbazol-2-yl)acetamide (5), 2-(2,2-ctimethoxyethyl)-1,2,4,5,6,7-hexahydro-3H-1,5-mediatioazocino[4,3-b]indol-3-one (6), 2-(2,2-dimethax-yethyl)-2,3,4,5,6,7-hocahydro-1H-1,5-methanoazocino[4,3-b]indole (7). The central step in these syntheses is the dehydrogenative reaction, which constructs the tetracyclic ring system from a much simpler tetracyclic precursor. The six-stable conformers of the compound (r were used for further calculations such as FT-IR, NMR, NLO, and FMO analyses, performed at the B3LYP/6-311++G(d,p) level. This work revealed that (7) can be a good material to use in the non-linear optical material because its beta tensor is greater ten times than that of the urea.
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) and the Sivas Cumhuriyet University scientific research projects department (Project No: CUBAP: EGT-090). All calculations have been carried out at TUBITAK ULAKBIM, High Performance and Grid Computing Center (TRGrid e-Infrastructure), Turkey.
dc.identifier.doi10.1016/j.heliyon.2020.e04105
dc.identifier.issn2405-8440
dc.identifier.issue6en_US
dc.identifier.pmid32548324
dc.identifier.scopus2-s2.0-85085938420
dc.identifier.scopusqualityQ1
dc.identifier.urihttps://doi.org/10.1016/j.heliyon.2020.e04105
dc.identifier.urihttps://hdl.handle.net/20.500.11776/7304
dc.identifier.volume6
dc.identifier.wosWOS:000549393200012
dc.identifier.wosqualityN/A
dc.indekslendigikaynakWeb of Science
dc.indekslendigikaynakScopus
dc.indekslendigikaynakPubMed
dc.institutionauthorUludağ, Nesimi
dc.language.isoen
dc.publisherElsevier Sci Ltd
dc.relation.ispartofHeliyon
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanıen_US
dc.rightsinfo:eu-repo/semantics/openAccess
dc.subjectTheoretical chemistry
dc.subjectOrganic chemistry
dc.subjectStrychnos alkaloids
dc.subjectFT-IR
dc.subjectNMR
dc.subjectNLO
dc.subjectFMO
dc.subjectConcise Total-Synthesis
dc.subjectSpectroscopic Ft-Ir
dc.subjectHomo-Lumo
dc.subjectOptical-Properties
dc.subjectNmr
dc.subjectNlo
dc.subjectNbo
dc.subjectMep
dc.subjectFmo
dc.subjectReduction
dc.titleNew route for synthesis of 2-(2,2-dimethoxyethyl)-1,2,3,4,5,6-hexahydro-1,5-methanoazocino[4,3-b] indole and DFT investigation
dc.typeArticle

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