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
dc.contributor.author | Uludağ, Nesimi | |
dc.contributor.author | Serdaroğlu, Goncagül | |
dc.date.accessioned | 2022-05-11T14:31:04Z | |
dc.date.available | 2022-05-11T14:31:04Z | |
dc.date.issued | 2020 | |
dc.identifier.issn | 2405-8440 | |
dc.identifier.uri | https://doi.org/10.1016/j.heliyon.2020.e04105 | |
dc.identifier.uri | https://hdl.handle.net/20.500.11776/7304 | |
dc.description.abstract | Development 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. | en_US |
dc.description.sponsorship | Scientific 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] | en_US |
dc.description.sponsorship | This 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. | en_US |
dc.language.iso | eng | en_US |
dc.publisher | Elsevier Sci Ltd | en_US |
dc.identifier.doi | 10.1016/j.heliyon.2020.e04105 | |
dc.rights | info:eu-repo/semantics/openAccess | en_US |
dc.subject | Theoretical chemistry | en_US |
dc.subject | Organic chemistry | en_US |
dc.subject | Strychnos alkaloids | en_US |
dc.subject | FT-IR | en_US |
dc.subject | NMR | en_US |
dc.subject | NLO | en_US |
dc.subject | FMO | en_US |
dc.subject | Concise Total-Synthesis | en_US |
dc.subject | Spectroscopic Ft-Ir | en_US |
dc.subject | Homo-Lumo | en_US |
dc.subject | Optical-Properties | en_US |
dc.subject | Nmr | en_US |
dc.subject | Nlo | en_US |
dc.subject | Nbo | en_US |
dc.subject | Mep | en_US |
dc.subject | Fmo | en_US |
dc.subject | Reduction | en_US |
dc.title | 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 | en_US |
dc.type | article | en_US |
dc.relation.ispartof | Heliyon | en_US |
dc.department | Fakülteler, Fen Edebiyat Fakültesi, Kimya Bölümü | en_US |
dc.identifier.volume | 6 | en_US |
dc.identifier.issue | 6 | en_US |
dc.institutionauthor | Uludağ, Nesimi | |
dc.relation.publicationcategory | Makale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanı | en_US |
dc.authorscopusid | 6507868758 | |
dc.authorscopusid | 36447801100 | |
dc.authorwosid | Serdaroğlu, Goncagül/I-6780-2016 | |
dc.identifier.wos | WOS:000549393200012 | en_US |
dc.identifier.scopus | 2-s2.0-85085938420 | en_US |
dc.identifier.pmid | 32548324 | en_US |
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