[3 + 2] cycloaddition of 1-(4-Methoxybenzyl)indoles and azaindoles with nitrile oxides. (7th May 2022)

• Record Type: Journal Article
• Authors: Kimura, Reina; Sato, Yoshihiro; Morisaki, Kazuhiro; Nishi, Takahide
• Is Part Of: Tetrahedron. Volume 113(2022)
• Publication Date: 2022-05-07
• Subjects: [3 + 2] cycloaddition -- 1-(4-methoxybenzyl)indoles -- 1-(4-methoxybenzyl)azaindoles -- nitrile oxides; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2022.132760
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: We studied [3 + 2] cycloaddition reactions of indoles and azaindoles with various nitrile oxides. N -Protection of indoles and azaindoles with the 4-methoxybenzyl group was found to be effective for [3 + 2] cycloaddition with nitrile oxides. Due to the propensity of the nitrile oxides to dimerize, it was necessary to optimize reaction conditions in the case of unstable nitrile oxides. This method was used to synthesize various key intermediates of biologically active 3-substituted azaindole derivatives. Graphical abstract: Image 1