Continued Exploration of Trifunctional Alkyl 4-Chloro-2-diazo-3-oxobutanoates: Streamlined Entry into [1,2,3]Triazolo[5,1-c][1,4]benzoxazines and [1,2,3]Triazolo[5,1-c][1,4]benzoxazepines

Abstract

Further exploration of the trifunctional character of previously introduced alkyl 4-chloro-2-diazo-3-oxobutanoates in reactions with N-protected substituted o-aminophenols followed by deprotection provided a convenient entry into [1,2,3]triazolo[5,1-c][1,4]benzoxazines, which are of high medicinal importance, as documented in the literature. The same approach applied to N-protected substituted o-(aminomethyl)phenols afforded [1,2,3]triazolo[5,1-c][1,4]benzoxazepines, which are practically unexplored compounds from a medicinal chemistry perspective. The syntheses start with S_N2-type alkylation of the phenol. Removal of the protecting group triggers imine formation followed by Wolff 1,2,3-triazole synthesis.

Key words

diazo compounds - multicenter reactions - nucleophilic substitution - domino reactions - Wolff 1,2,3-triazole synthesis - benzoxazines - benzoxazepines

Publikationsverlauf

Eingereicht: 12. November 2020

Angenommen: 08. Januar 2021

Accepted Manuscript online:
08. Januar 2021

Artikel online veröffentlicht:
09. Februar 2021

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