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

Literature Information

Publication Date 2023-11-15
DOI 10.1039/D3OB01835K
Impact Factor 3.876
Authors

Lei Huang, Yan Wang, Xin Liu, Shi-Kai Tian


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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.

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Organic & Biomolecular Chemistry

Organic & Biomolecular Chemistry
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Organic & Biomolecular Chemistry (OBC) publishes original and high impact research and reviews in organic chemistry. We welcome research that shows new or significantly improved protocols or methodologies in total synthesis, synthetic methodology or physical and theoretical organic chemistry as well as research that shows a significant advance in the organic chemistry or molecular design aspects of chemical biology, catalysis, supramolecular and macromolecular chemistry, theoretical chemistry, mechanism-oriented physical organic chemistry, medicinal chemistry or natural products. Articles published in the journal should report new work which makes a highly-significant impact in the field. Routine and incremental work is generally not suitable for publication in the journal. More details about key areas of our scope are below. In all cases authors should include in their article clear rationale for why their research has been carried out.

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