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DOI: 10.1055/s-0040-1720865
Atropisomeric Properties of 9-Methyl-1,4-benzodiazepin-2-ones
This work was supported in part by a Grant-in-Aid for Scientific Research (C) (19K06980) from the Japan Society for the Promotion of Science. H.T. is grateful for financial support from the Hoansha Foundation.
Abstract
The atropisomeric and conformational properties of 1,4-benzodiazepin-2-ones were investigated by freezing the conformation with a methyl group at the C9 of 1,4-benzodiazepine. It was revealed that 1,4-benzodiazepin-2-ones exist only as a pair of enantiomers [(a1 R, a2 S) and (a1 S, a2 R)], which was confirmed by X-ray analysis. The absolute configuration of each atropisomer was deduced by comparing the [α]D and CD data with those of (–)-N-methoxycarbonylmethylated 9-methyl-5-phenyl-1,4-benzodiaepin-2-one derivative. It was elucidated that the corresponding N-methylated derivative showed similar CD spectra, although the rotational direction of [α]D was opposite to that of others.
Key words
atropisomerism - absolute configuration - 1,4-benzodiazepin-2-one - CD spectra - X-ray crystal structure analysisSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1720865.
- Supporting Information
Publikationsverlauf
Eingereicht: 28. Juni 2021
Angenommen nach Revision: 26. Juli 2021
Artikel online veröffentlicht:
27. August 2021
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