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Synthesis 2019; 51(09): 1949-1960
DOI: 10.1055/s-0037-1610684
DOI: 10.1055/s-0037-1610684
paper
Unexpected PF6 Anion Metathesis during the Bischler–Napieralski Reaction: Synthesis of 3,4-Dihydroisoquinoline Hexafluorophosphates and Their Tetrahydroisoquinoline Related Alkaloids
We thank the Colombian Institute for Science and Research (COLCIENCIAS) under the project No. RC-0346-2013 for the financial support.Further Information
Publication History
Received: 22 October 2018
Accepted after revision: 20 December 2018
Publication Date:
18 February 2019 (online)
Abstract
A series of N-phenethylcinnamamides were subjected to the Bischler–Napieralski reaction to furnish diverse 1-styryl-3,4-dihydroisoquinolines. We noticed that the desired products were unstable when the reaction was performed under conventional solvent conditions. However, when [bmim]PF6 was used as the reaction media, the nature of the Bischler–Napieralski reaction promoted an unusual in situ ionic interchange between this ionic liquid and the dihydroisoquinoline core that led to the stabilization of the desired 1-styryl-3,4-dihydroisoquinolines, allowing their isolation as hexafluorophosphate salts. Finally, the one-pot reduction/reductive methylation process afforded the N-methyl derivatives, establishing that our findings can be an efficient and useful strategy for the concise synthesis of tetrahydroisoquinoline alkaloids.
Key words
cinnamamide - Bischler–Napieralski reaction - dihydroisoquinoline hexafluorophosphate - Dysoxylum alkaloid - tetrahydroisoquinolineSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1610684.
- Supporting Information
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