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Nuclear magnetic resonance spectra of psychotherapeutic agents. V*—conformational analysis of 1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-2-ones

✍ Scribed by M. C. Aversa; P. Giannetto; G. Romeo; P. Ficarra; M. G. Vigorita

Publisher
John Wiley and Sons
Year
1981
Tongue
English
Weight
488 KB
Volume
15
Category
Article
ISSN
0749-1581

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✦ Synopsis

Abstract

The conformational analysis of biologically active lofendazam (7‐chloro‐5‐phenyl‐1,3,4,5‐tetrahydro‐2H‐1,5‐benzodiazepin‐2‐one) is carried out by means of lanthanide shift reagent assisted ^1^H NMR spectroscopy: the lanthanide induced shift computer simulation suggests that in deuteriochloroform the heterocyclic ring of lofendazam assumes a cycloheptene‐like chair conformation, where 1‐N moves away from trigonal stereochemistry to a very flattened pyramidal structure. At room temperature the conformational equilibrium is markedly shifted (85%) towards the conformer showing pseudoaxial H‐1 and 5‐Ph. The remarkable influence of steric requirements in controlling conformation, and the importance of 3‐ and/or 4‐methyl groups in hindering the ring inversion at room temperature, have been verified by conformational analysis of suitable analogous 1,3,4,5‐tetraydro‐2H‐1,5‐benzodiazepin‐2‐ones.

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