Facile Access to Triazole-Fused 3,1-Benzoxazines Enabled by Metal-Free Base-Promoted Intramolecular C–O Coupling

Stepan S. Tatevosyan; Yury N. Kotovshchikov; Gennadij V. Latyshev; Nikolay V. Lukashev; Irina P. Beletskaya

doi:10.1055/a-1623-2333

Synthesis, Table of Contents

Synthesis 2022; 54(02): 369-377
DOI: 10.1055/a-1623-2333

feature

Facile Access to Triazole-Fused 3,1-Benzoxazines Enabled by Metal-Free Base-Promoted Intramolecular C–O Coupling

Stepan S. Tatevosyan

,

Yury N. Kotovshchikov∗

,

Gennadij V. Latyshev

,

Nikolay V. Lukashev

,

Irina P. Beletskaya

Abstract

All articles of this category

In memory of Professor Ei-ichi Negishi (1935–2021).

Abstract

A convenient approach to assemble 1,2,3-triazole-fused 4H-3,1-benzoxazines has been developed. Diverse alcohol-tethered 5-iodotriazoles, readily accessible by a modified protocol of Cu-catalyzed (3+2)-cycloaddition, were utilized as precursors of the target fused heterocycles. The intramolecular C–O coupling proceeded efficiently under base-mediated transition-metal-free conditions, furnishing cyclization products in yields up to 96%. Suppression of the competing reductive cleavage of the C–I bond was achieved by the use of Na₂CO₃ in acetonitrile at 100 °C. This practical and cost-effective procedure features a broad substrate scope and valuable functional group tolerance.

Key words

triazoles - benzoxazines - heterocycles - fused-ring systems - C–O coupling - cycloaddition

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