Synthesis of Tricyclic Benzazocines by Aza-Prins Reaction

Synthesis of Tricyclic Benzazocines by Aza-Prins Reaction

The aza-Prins reaction of 3-vinyl­tetra­hydro­quinolines with aldehydes proceeded smoothly in the presence of hydrogen halides, and the tricyclic benzazocine derivatives were isolated in good to high yields. The reaction would proceed through the formation and cyclization of the iminium ion intermed...

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Veröffentlicht in:Organic letters 2017-01, Vol.19 (1), p.266-269
Hauptverfasser: Katamura, Tomohiro, Shimizu, Tomoaki, Mutoh, Yuichiro, Saito, Shinichi
Format: Artikel
Sprache:eng
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Zusammenfassung:The aza-Prins reaction of 3-vinyl­tetra­hydro­quinolines with aldehydes proceeded smoothly in the presence of hydrogen halides, and the tricyclic benzazocine derivatives were isolated in good to high yields. The reaction would proceed through the formation and cyclization of the iminium ion intermediate.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.6b03577