Syntheses and conformational analyses of some 3‐amino‐2,5‐dioxo‐2,3,4,5‐tetrahydro‐1H‐1‐benzazepine derivatives: X‐ray crystal structure of 35–3‐[[(1,1‐dimethylethoxy)carbonyl]amino]‐2,5‐dioxo‐2,3,4,5‐tetrahydro‐1H‐1‐benzazepine

Jonathan B. Ball, Margaret G. Wong, Benny Capuano, Jacqueline M. Gulbis, Maureen F. Mackay, Paul F. Alewood

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The constrained dipeptide mimic 1 was synthesized from 2 in three steps with 65% overall yield. Analyses of the 1H nmr data of a number of 3‐amino‐2,5‐dioxo‐2,3,4,5‐tetrahydro‐1H‐1‐benzazepine derivatives led to the conclusion that these compounds adopt a similar conformation and that this ring system is rigid. X‐ray crystallography was used to define the structure of 3, and computer‐aided energy minimization of 6 gave a preferred conformation similar to that observed in the crystal of 3.

Original languageEnglish
Pages (from-to)279-286
Number of pages8
JournalJournal of Heterocyclic Chemistry
Issue number2
Publication statusPublished - 1 Jan 1990
Externally publishedYes

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