Organic Magnetic Resonance p. 394 - 398 (1981)
Update date:2022-07-29
Topics:
Aversa, M.C.
Giannetto, P.
Romeo, G.
Ficarra, P.
Vigorita, M.G.
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 1H 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 (85percent) towards the conformer showing pseudoaxial H-1 and 5-Ph.The remarkable influence of steric requirements is 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-tetrahydro-2H-1,5-benzodiazepin-2-ones.
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Doi:10.1021/jo200020z
(2011)Doi:10.1021/jo00337a046
(1981)Doi:10.1246/bcsj.54.1456
(1981)Doi:10.1002/ejic.200300605
(2004)Doi:10.1021/ja00531a054
(1980)Doi:10.1016/S0040-4020(01)92350-6
(1981)