Molecules (Jun 2023)

Stereochemistry of <i>N</i>-Acyl-5<i>H</i>-dibenzo[<i>b</i>,<i>d</i>]azepin-7(6<i>H</i>)-ones

  • Arisa Chiba,
  • Ryoko Tanaka,
  • Mayuno Hotta,
  • Kayo Nakamura,
  • Kosho Makino,
  • Hidetsugu Tabata,
  • Tetsuta Oshitari,
  • Hideaki Natsugari,
  • Hideyo Takahashi

DOI
https://doi.org/10.3390/molecules28124734
Journal volume & issue
Vol. 28, no. 12
p. 4734

Abstract

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The stereochemical properties of N-acyl-5H-dibenzo[b,d]azepin-7(6H)-ones (2a–c), which inhibit potassium channels in T cells, were examined by freezing their conformational change due to 4-methyl substitution. N-Acyl-5H-dibenzo[b,d]azepin-7(6H)-ones exist as pairs of enantiomers [(a1R, a2R), (a1S, a2S)], and each atropisomer is separable at room temperature. An alternate procedure for preparing 5H-dibenzo[b,d]azepin-7(6H)-ones involves the intramolecular Friedel–Crafts cyclization of N-benzyloxycarbonylated biaryl amino acids. Consequently, the N-benzyloxy group was removed during the cyclization reaction to produce 5H-dibenzo[b,d]azepin-7(6H)-ones suitable for the subsequent N-acylation reaction.

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