Ring Enlargement Reaction of C,N-Cyclic‑N′‑acyl Azomethine Imines with Sulfonium Ylide: An Efficient Synthesis of 3‑Benzazepine Derivatives

Highly efficient formation of 3-benzazepine derivatives has been achieved, based on the ring expansion reaction of C,N-cyclic-N′-acyl azomethine imines with sulfonium ylide generated in situ from the corresponding sulfonium salt. The reactions proceeded smoothly to afford the tricyclic 3-benzazepine...

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Veröffentlicht in:Organic letters 2014-09, Vol.16 (18), p.4854-4857
Hauptverfasser: Soeta, Takahiro, Ohgai, Takahiro, Sakai, Takahiro, Fujinami, Shuhei, Ukaji, Yutaka
Format: Artikel
Sprache:eng
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Zusammenfassung:Highly efficient formation of 3-benzazepine derivatives has been achieved, based on the ring expansion reaction of C,N-cyclic-N′-acyl azomethine imines with sulfonium ylide generated in situ from the corresponding sulfonium salt. The reactions proceeded smoothly to afford the tricyclic 3-benzazepine derivatives in good to high yields. A wide range of C,N-cyclic N′-acyl azomethine imines were applicable to this reaction.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol502347n