Journal article

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 3S-3-[[(1,1-DIMETHYLETHOXY)CARBONYL]AMINO]-2,5-DIOXO-2,3,4,5-TETRAHYDRO-1H-1-BENZAZEPINE

JB BALL, MG WONG, B CAPUANO, JM GULBIS, MF MACKAY, PF ALEWOOD

JOURNAL OF HETEROCYCLIC CHEMISTRY | HETERO CORPORATION | Published : 1990

Abstract

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. Copyright © 1990 Journal of Heterocyclic Chemistry