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Synthesis and 1H and 13C NMR structural analysis of cis- and trans-2-imino-1,3- and -3,1-perhydrobenzoxazines and their 3- and 1-N-methyl derivatives

✍ Scribed by Kalevi Pihlaja; Jari Sinkkonen; Ferenc Fülöp

Publisher
John Wiley and Sons
Year
2003
Tongue
English
Weight
133 KB
Volume
41
Category
Article
ISSN
0749-1581

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✦ Synopsis

Abstract

cis‐ and trans‐2‐imino‐1,3‐ and ‐3,1‐perhydrobenzoxazines and the N‐methyl derivatives of the latter were synthesized from the corresponding cyclic 1,3‐amino alcohol with cyanogen bromide. The configurations of the studied compounds were confirmed by ^1^H and ^13^C NMR spectra. All trans‐fused compounds exist in biased chair–chair conformations as expected, whereas the cis‐fused 1,3‐benzoxazines attain exclusively the O‐in conformations. The cis‐fused 3,1‐benzoxazines, especially the 1‐methyl‐substituted derivatives, tend to favor the N‐out form, obviously owing to the favorable axial orientation of this N‐methyl. Copyright © 2003 John Wiley & Sons, Ltd.

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