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

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 availabl...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2023-12, Vol.21 (47), p.9321-9325
Main Authors: Huang, Lei, Wang, Yan, Liu, Xin, Tian, Shi-Kai
Format: Article
Language:English
Subjects:
Ammonium
Ammonium salts
Functional groups
Quaternary ammonium salts
Reagents
Thiols
Transition metals
Tributylamine
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Summary: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.
ISSN:1477-0520
1477-0539
DOI:10.1039/d3ob01835k