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Stereochemistry of IN/I-Acyl-5IH/I-dibenzoIb/I,Id/Iazepin-7-ones
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Stereochemistry of IN/I-Acyl-5IH/I-dibenzoIb/I,Id/Iazepin-7-ones
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Journal Article
Stereochemistry of IN/I-Acyl-5IH/I-dibenzoIb/I,Id/Iazepin-7-ones
2023
Overview
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 [(a[sup.1]R, a[sup.2]R), (a[sup.1]S, a[sup.2]S)], 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.
Publisher
MDPI AG
Subject
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