Methylene Insertion into Nitrogen‐Heteroatom Single Bonds of 1,2‐Azoles via a Zinc Carbenoid: An Alternative Tool for Skeletal Editing

Authors: Masato Tsuda, Taiki Morita, Yuto Morita, Jun Takaya, Hiroyuki Nakamura

Published: 2023-12-27

DOI: 10.1002/advs.202307563

Source: Full article

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Abstract

AbstractThe nitrogen‐heteroatom single bonds of 1,2‐azoles and isoxazolines underwent methylene insertion in the presence of CH2I2 (6 equiv.) and diethylzinc (3 equiv.) to produce a wide variety of the ring‐expanded six‐membered heterocycles. Density functional theory calculations suggest that the methylene insertion proceeds via cleavage of nitrogen‐heteroatom single bonds followed by ring closure.