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Unexpected isomerization of new naphth[1,3]oxazino[2,3-a] isoquinolines in solution, studied by dynamic NMR and supported by theoretical DFT computations

  • Through the reactions of 1-aminomethyl-2-naphthol and substituted 1-aminobenzyl-2-naphthols with 3,4-dihydroisoquinoline or 6,7-dimethoxy-3,4-dihydroisoquinoline under microwave conditions, naphth[1,2-e][1,3]oxazino[2,3-a]-isoquinoline derivatives were prepared in good yields. The latter reaction was extended by using 2-aminoarylmethyl-1-naphthols, leading to isomeric naphth-[2,1-e][1,3]oxazino[2,3-a] isoquinolines. Beside the detailed NMR spectroscopic and theoretical study of both stereochemistry and dynamic behaviour of these new conformational flexible heterocyclic ring systems an unexpected dynamic process between two diastereomers was observed in solution, studied by variable temperature H-1 NMR spectroscopy and the mechanism proved by theoretical DFT computations.

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Metadaten
Author:Istvan Szatmari, Matthias Heydenreich, Andreas Koch, Ferenc Fülöp, Erich Kleinpeter
DOI:https://doi.org/10.1016/j.tet.2013.06.094
ISSN:0040-4020 (print)
Parent Title (English):Tetrahedron
Publisher:Elsevier
Place of publication:Oxford
Document Type:Article
Language:English
Year of first Publication:2013
Year of Completion:2013
Release Date:2017/03/26
Tag:3,4-Dihydroisoquinoline; Aminonaphthol; Conformational analysis; DFT calculations; Dynamic NMR spectroscopy
Volume:69
Issue:35
Pagenumber:11
First Page:7455
Last Page:7465
Funder:Bolyai Janos Fellowship
Organizational units:Mathematisch-Naturwissenschaftliche Fakultät / Institut für Chemie
Peer Review:Referiert