A New Method of Constructing Methyleneindene and Quinoline Frameworks from Methylenecyclopropanes

Qu-Hang Yang; Min Shi; Yin Wei

doi:10.1002/asia.202400411

A New Method of Constructing Methyleneindene and Quinoline Frameworks from Methylenecyclopropanes

Chem Asian J. 2024 May 8:e202400411. doi: 10.1002/asia.202400411. Online ahead of print.

Authors

Qu-Hang Yang¹, Min Shi², Yin Wei³

Affiliations

¹ East China University of Science and Technology, School of Chemistry & Molecular Engineering, Shanghai, CHINA.
² Shanghai Institute of Organic Chemistry Chinese Academy of Sciences, State Key Laboratory of Organometallic Chemistry, Shanghai, CHINA.
³ Shanghai Institute of Organic Chemistry, State Key Laboratory of Organometallic Chemistry, 345 Lingling Road, 200032, Shanghai, CHINA.

PMID: 38719729
DOI: 10.1002/asia.202400411

Abstract

In this paper, we have established an operationally convenient protocol for the rapid construction of polysubstituted methyleneindene and quinoline derivatives under mild conditions. This new synthetic method is achieved through the conversion of acetyl-substituted methylenecyclopropanes with TsOH·H2O and ortho-amino-substituted methylenecyclopropanes with aromatic aldehyde and TsOH·H2O, respectively. A variety of transformations of the obtained products was demonstrated. The plausible reaction mechanisms were also proposed.

Keywords: Organic synthesis; methylenecyclopropane; methyleneindene; quinoline.