NMR Study on Rotational Isomerism in a Lactam-Type 5-(2-Fluorophenyl)-1,4-benzodiazepine

✍ Scribed by Emil Finner; Horst Zeugner; Wolfgang Milkowski

• Publisher: John Wiley and Sons
• Year: 1984
• Tongue: English
• Weight: 175 KB
• Volume: 317
• Category: Article
• ISSN: 0365-6233
• DOI: 10.1002/ardp.19843170416

✦ Synopsis

Various valuable publications on topographical and electronic aspects of the structure-activity relationships (SAR) of 5-aryl-l,4-benzodiazepin-2-ones are known"5). However, to our surprise we found, that in all these reports conformational preferences of the 5-aryl ring were almost totally ignored. The objective of the present studies is two-fold: (i) to give experimental proof of a rotational isomerism'' and (ii) to evaluate the transmission of electronic effects as probed by 13C chemical shifts. 6,8-Dimethyl-5-(2-fluorophenyl)-l-methyl-l,3-dihydro-2H-l,4-benzodiazepin-2-one (KC 6165) was chosen as a model compound for our studies.

'H-13C shift correlation refering to Fig. 1, homonuclear 'H saturation transfer experiments and some selective 13G{ 'H} decouplings.