Issue 19, 2023

Ring expansion/opening reactions of epoxy ene-amides: access to azabicyclononene, tetrahydropyridine and tetrazole scaffolds

Abstract

Ene-sulfonamides, obtained from epoxy (terminal as well as internal) benzenesulfonamide and substituted chloro-acrylaldehydes, undergo Lewis acid (BF3·OEt2) catalysed cyclisation to afford azabicyclononene, tetrahydropyridinyl benzoate or tetrahydropyridine-carbaldehyde scaffolds depending on the substrate. In the presence of Me3SiN3, substituted tetrazoles are readily obtained. Key products have been characterized by single-crystal X-ray crystallography.

Graphical abstract: Ring expansion/opening reactions of epoxy ene-amides: access to azabicyclononene, tetrahydropyridine and tetrazole scaffolds

Supplementary files

Article information

Article type
Paper
Submitted
03 feb 2023
Accepted
10 apr 2023
First published
11 apr 2023

New J. Chem., 2023,47, 9061-9065

Ring expansion/opening reactions of epoxy ene-amides: access to azabicyclononene, tetrahydropyridine and tetrazole scaffolds

Suraj and K. C. K. Swamy, New J. Chem., 2023, 47, 9061 DOI: 10.1039/D3NJ00529A

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