Issue 47, 2023

Convenient synthesis of thiolated 2,7-disubstituted tropones via double C–N bond cleavage of tropinone derivatives

Abstract

A range of 2,4-dialkylidenetropinone-derived quaternary ammonium salts smoothly reacted with thiols in the presence of tributylamine, delivering structurally diverse thiolated 2,7-disubstituted tropones in moderate to excellent yields with high site selectivity. The reaction employs readily available feedstocks and reagents, is free of transition metals, tolerates various functional groups, and can be easily scaled up.

Graphical abstract: Convenient synthesis of thiolated 2,7-disubstituted tropones via double C–N bond cleavage of tropinone derivatives

Supplementary files

Article information

Article type
Communication
Submitted
10 Nov 2023
Accepted
13 Nov 2023
First published
15 Nov 2023

Org. Biomol. Chem., 2023,21, 9321-9325

Convenient synthesis of thiolated 2,7-disubstituted tropones via double C–N bond cleavage of tropinone derivatives

L. Huang, Y. Wang, X. Liu and S. Tian, Org. Biomol. Chem., 2023, 21, 9321 DOI: 10.1039/D3OB01835K

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