• search hit 10 of 18
Back to Result List

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.

Export metadata

Additional Services

Search Google Scholar Statistics
Metadaten
Author details:Istvan SzatmariORCiD, Matthias HeydenreichORCiD, Andreas KochORCiDGND, Ferenc FulopORCiD, Erich KleinpeterORCiDGND
DOI:https://doi.org/10.1016/j.tet.2013.06.094
ISSN:0040-4020
Title of parent work (English):Tetrahedron
Publisher:Elsevier
Place of publishing:Oxford
Publication type:Article
Language:English
Year of first publication:2013
Publication year:2013
Release date:2017/03/26
Tag:3,4-Dihydroisoquinoline; Aminonaphthol; Conformational analysis; DFT calculations; Dynamic NMR spectroscopy
Volume:69
Issue:35
Number of pages:11
First page:7455
Last Page:7465
Funding institution:Bolyai Janos Fellowship
Organizational units:Mathematisch-Naturwissenschaftliche Fakultät / Institut für Chemie
Peer review:Referiert
Accept ✔
This website uses technically necessary session cookies. By continuing to use the website, you agree to this. You can find our privacy policy here.