Atropisomeric Properties of N-Acyl/N-Sulfonyl 5H-Dibenzo[b,d]azepin-7(6H)-ones.

ABSTRACT: The stereochemistry of N-acyl/N-sulfonyl 5H-dibenzo[b,d]azepin-7(6H)-ones (I, II) was examined in detail by freezing the conformation with a methyl group at the C-4 of dibenzoazepine. Because the two axes (axis 1, axis 2) move together concertedly, I and II exist only as a pair of enantiomers [(a¹R, a²R) and (a¹S, a²S)], which was confirmed by X-ray analysis of IIBc. It was elucidated that the amide derivatives I exist in equilibrium with the E/Z-amide (100:2-100:34), which means that the exocyclic bond (axis 3) is not in concert with the endocyclic axes (axis 1, axis 2). For the preparation of 5H-dibenzo[b,<

SUBMITTER: Namba T 

PROVIDER: S-EPMC8279494 | biostudies-literature | 2021 Jun

REPOSITORIES: biostudies-literature