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

ABSTRACT: The nitrogen-heteroatom single bonds of 1,2-azoles and isoxazolines underwent methylene insertion in the presence of CH2 I2 (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.

SUBMITTER: Tsuda M 

PROVIDER: S-EPMC10933618 | biostudies-literature | 2024 Mar

REPOSITORIES: biostudies-literature

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

Tsuda Masato M   Morita Taiki T   Morita Yuto Y   Takaya Jun J   Nakamura Hiroyuki H  

Advanced science (Weinheim, Baden-Wurttemberg, Germany) 20231226 10

The nitrogen-heteroatom single bonds of 1,2-azoles and isoxazolines underwent methylene insertion in the presence of CH<sub>2</sub> I<sub>2</sub> (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. ...[more]

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