2-Alkynylbenzaldoxime: a versatile building block for the generation of N-heterocycles

Organic & Biomolecular Chemistry Pub Date: 2014-09-17 DOI: 10.1039/C4OB01618A

Abstract

2-Alkynylbenzaldoxime as a versatile building block has been applied widely for the construction of N-heterocycles in organic synthesis. Since it could be easily transferred to isoquinoline N-oxide via intramolecular 6-endo cyclization in the presence of metal catalysts or electrophiles, the subsequent [3 + 2] cycloaddition/nucleophilic addition and rearrangement could be expected. On the other hand, a Beckmann rearrangement could occur first since an oxime moiety is present in the molecule, which would then undergo an intramolecular cyclization to furnish nitrogen-containing heterocycles. This review reports the recent advancement in the generation of N-heterocycles starting from 2-alkynylbenzaldoximes via tandem reactions based on different reaction types.

Graphical abstract: 2-Alkynylbenzaldoxime: a versatile building block for the generation of N-heterocycles
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