Synthesis of Tetrahydropyridine Derivatives through a Reaction of 1,6-Enynes, Sulfur Dioxide, and Aryldiazonium Tetrafluoroborates.

doi:10.1021/acs.orglett.7b03195

Paper

Synthesis of Tetrahydropyridine Derivatives through a Reaction of 1,6-Enynes, Sulfur Dioxide, and Aryldiazonium Tetrafluoroborates.

Published Oct 24, 2017 · Yuanyuan An, Jie Wu

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Abstract

Sulfonated tetrahydropyridine derivatives are accessed through a radical reaction of 1,6-enynes, sulfur dioxide, and aryldiazonium tetrafluoroborates under mild conditions. Sulfonated pyrrolidine can be generated when terminal alkyne is used as the substrate. This reaction proceeds efficiently in dichloroethane without the addition of any catalysts or additives, providing sulfonated tetrahydropyridine derivatives in moderate to good yields. During this transformation, aryldiazonium tetrafluoroborates cooperate with DABCO·(SO2)2 leading to sulfonyl radicals, which initiate the radical cyclization process. Two molecules of aryldiazonium tetrafluoroborates are involved in the reaction.

Study Snapshot

This study demonstrates a simple, efficient, and cost-effective method for synthesis of sulfonated tetrahydropyridine derivatives in moderate to good yields using 1,6-enynes, sulfur dioxide, and aryldiazonium tetrafluoroborates

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

Synthesis of Tetrahydropyridine Derivatives through a Reaction of 1,6-Enynes, Sulfur Dioxide, and Aryldiazonium Tetrafluoroborates.

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Citations

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