Work

Copper-catalyzed domino cyclization of anilines and cyclobutanone oxime: a scalable and versatile route to spirotetrahydroquinoline derivatives

Year: 2025

Type: article

Abstract: In this study, we report the copper-catalyzed synthesis of tetrahydroquinoline derivatives via a domino reaction of aniline with cyclobutanone oxime. This method demonstrates a selective approach for generating bioactive tetrahydroquinoline scaffolds, which have broad applications in pharmaceutical chemistry. The reaction conditions were optimized for the effective formation of tetrahydroquinoline derivatives with varying substituents, showing high yields under mild conditions. Mechanistic studies suggest a catalytic cycle involving nucleophilic attack by the aniline on the cyclobutanone oxime, followed by cyclization to form the desired product.

Source: Beilstein Journal of Organic Chemistry

DOI: 10.3762/bjoc.21.58

Authors: Qingqing Jiang, Xinyi Lei, Pan Gao, Yu Yuan

Institution: Yangzhou University

Language: English

Topic: Multicomponent Synthesis of Heterocycles

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: diamond

Funders: China Postdoctoral Science Foundation, Government of Jiangsu Province, Natural Science Foundation of Jiangsu Province

Awards: G3708574499, G8797829695