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

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

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

Author(s) -

Ball Jonathan B.,

Wong Margaret G.,

Capuano Benny,

Gulbis Jacqueline M.,

Mackay Maureen F.,

Alewood Paul F.

Publication year - 1990

Publication title -

journal of heterocyclic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.321

H-Index - 59

eISSN - 1943-5193

pISSN - 0022-152X

DOI - 10.1002/jhet.5570270231

Subject(s) - chemistry , dipeptide , benzazepine , yield (engineering) , ring (chemistry) , crystal structure , x ray , energy minimization , crystallography , stereochemistry , peptide , computational chemistry , organic chemistry , biochemistry , materials science , physics , quantum mechanics , metallurgy

The constrained dipeptide mimic 1 was synthesized from 2 in three steps with 65% overall yield. Analyses of the 1 H nmr data of a number of 3‐amino‐2,5‐dioxo‐2,3,4,5‐tetrahydro‐1 H ‐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 .

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