4.5 Article

Steric Push towards the [n+3] Hydrated Imidazoline Ring Expansion (HIRE) of Dibenzo[1.4]oxazepines and Thiazepines

Journal

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2022, Issue 35, Pages -

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.202200818

Keywords

Aminoethanols; Ring-expansion reaction; Heterocycles; Synthetic methods

Funding

  1. Russian Science Foundation [22-23-00439]

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The influence of introducing substituents of increasing bulk in the alpha position of tetracyclic imidazoline-fused heteroazepinones on the course of hydrated imidazoline ring expansion (HIRE) reaction has been established.
The influence of introducing substituents of increasing bulk in alpha position of tetracyclic imidazoline-fused heteroazepinones on the course of hydrated imidazoline ring expansion (HIRE) reaction was established. Under certain conditions, substituted beta-aminoethanols can be used to obtain solely the ring expanded products from dibenzo[b,f][1,4]ox(thi)azepin-11(10H)-ones while with their unsubstituted counterparts, side chain expulsion was the only observable outcome.

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