Issue 12, 2022

Synthesis of isoxazoloazaborines via gold(i)-catalyzed propargyl aza-Claisen rearrangement/borylative cyclization cascade

Abstract

Isoxazoloazaborines 3 and 5 have been synthesized from 4-N-propargylaminoisoxazole 1via gold(I)-catalyzed propargyl aza-Claisen rearrangement followed by electrophilic borylative cyclization in 27–86% yields. In situ generation of isoxazole 2 having an amino group and allenyl functionality is essential to give highly substituted isoxazoloazaborines 3 and 5, although the conventional propargyl aza-Claisen rearrangement readily affords the corresponding nitrogen-containing heterocycles, such as pyridines and pyrroles. The resulting isoxazoloazaborine 5a underwent the N–O bond insertion of zinc carbenoid to give oxazine-fused azaborine 6 in 48% yield.

Graphical abstract: Synthesis of isoxazoloazaborines via gold(i)-catalyzed propargyl aza-Claisen rearrangement/borylative cyclization cascade

Supplementary files

Article information

Article type
Communication
Submitted
13 Des 2021
Accepted
11 Jan 2022
First published
11 Jan 2022

Chem. Commun., 2022,58, 1942-1945

Synthesis of isoxazoloazaborines via gold(I)-catalyzed propargyl aza-Claisen rearrangement/borylative cyclization cascade

M. Tsuda, T. Morita and H. Nakamura, Chem. Commun., 2022, 58, 1942 DOI: 10.1039/D1CC07002A

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