Conformation Analyses, Dynamic Behavior and Amide Bond Distortions of Medium-sized Heterocycles. 1. Partially and Fully Reduced 1-Benzazepines
2005; American Chemical Society; Volume: 70; Issue: 5 Linguagem: Inglês
10.1021/jo048118b
ISSN1520-6904
AutoresM. Qadir, J. Cobb, Peter Sheldrake, N. Whittall, Andrew J. P. White, King Kuok Hii, Peter N. Horton, Michael B. Hursthouse,
Tópico(s)Asymmetric Synthesis and Catalysis
ResumoFive 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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