An Ugi Reaction/Intramolecular Cyclization/Oxidation Cascade towards Tetrazole-Linked Dibenzoxazepines

Qiang Zheng; André Boltjes; Alexander Dömling

doi:10.1055/s-0040-1706642

Synthesis, Table of Contents

Synthesis 2021; 53(11): 1980-1988
DOI: 10.1055/s-0040-1706642

paper

An Ugi Reaction/Intramolecular Cyclization/Oxidation Cascade towards Tetrazole-Linked Dibenzoxazepines

Qiang Zheng

,

André Boltjes

,

Alexander Dömling ∗

Abstract

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In memoriam Albert van Leusen

Abstract

A series of tetrazole-linked dibenzo[b,f][1,4]oxazepines is synthesized through a short sequence involving an Ugi tetrazole reaction. The intermediate tetrazole undergoes a potassium carbonate mediated S_NAr cyclization, followed by oxidation to afford the target tricyclic heterocyclic scaffold. The optimization, scope and limitations of this two-step and efficient methodology are investigated. A 1000-member library of tetrazole-linked dibenzo[b,f][1,4]oxazepines is generated and the physicochemical properties are analyzed. great

Key words

dibenzo[b,f][1,4]oxazepines - Ugi tetrazole - cyclization - library - drug-like properties

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References

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