Atropisomeric Properties of 9-Methyl-1,4-benzodiazepin-2-ones

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 [(a (1) R , a (2) S ) and (a (1) S , a (2)...

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Published inSynthesis (Stuttgart) Vol. 53; no. 24; pp. 4682 - 4688
Main Authors Tanaka, Ryoko, Makino, Kosho, Tabata, Hidetsugu, Oshitari, Tetsuta, Natsugari, Hideaki, Takahashi, Hideyo
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 17.12.2021
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
VASOPRESSIN RECEPTOR
ACTIVE CONFORMATION
1,4-benzodiazepin-2-one
X-ray crystal structure analysis
LIGANDS
AXIAL CHIRALITY
absolute configuration
CD spectra
atropisomerism
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Summary: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 [(a (1) R , a (2) S ) and (a (1) S , a (2) R )], which was confirmed by X-ray analysis. The absolute configuration of each atropisomer was deduced by comparing the [alpha] (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 [alpha] (D) was opposite to that of others.
ISSN:0039-7881
1437-210X
DOI:10.1055/s-0040-1720865