Conformation analyses, dynamic behavior and amide bond distortions of medium-sized heterocycles. 1. Partially and fully reduced 1-benzazepines.
J Org Chem
; 70(5): 1545-51, 2005 Mar 04.
Article
em En
| MEDLINE
| ID: mdl-15730272
ABSTRACT
Five 1-benzazepine heterocycles were synthesized by utilizing transition-metal-catalyzed processes in key bond-forming steps. exo-Methylene and methyl substituents were introduced at position 5, as well as a unit of unsaturation between positions 3 and 4, with benzoyl or benzyl N-substituents. Solution- and solid-state structures were examined, using dynamic NMR spectroscopy and X-ray crystallography, corroborated by molecular mechanics calculations. Greater amide distortion is associated with a more stable ground-state structure, which is in turn more reluctant to undergo conformational changes.
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Base de dados:
MEDLINE
Assunto principal:
Benzazepinas
/
Amidas
/
Compostos Heterocíclicos com 2 Anéis
Idioma:
En
Ano de publicação:
2005
Tipo de documento:
Article