Unexpected PF6 Anion Metathesis during the Bischler–Napieralski Reaction: Synthesis of 3,4-Dihydroisoquinoline Hexafluorophosphates and Their Tetrahydroisoquinoline Related Alkaloids

Carlos E. Puerto Galvis; Mario A. Macías; Vladimir V. Kouznetsov

doi:10.1055/s-0037-1610684

Synthesis, Table of Contents

Synthesis 2019; 51(09): 1949-1960
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

Carlos E. Puerto Galvis

^aLaboratorio de Química Orgánica y Biomolecular, CMN, Universidad Industrial de Santander, Parque Tecnológico Guatiguará, Km 2 Vía Refugio, Piedecuesta 681011, Colombia Email: kouznet@uis.edu.co Email: vkuznechnik@gmail.com

,

Mario A. Macías

^bDepartment of Chemistry, Universidad de los Andes, Carrera 1 No. 18A 10, Bogotá 111711, Colombia

,

Vladimir V. Kouznetsov *

^aLaboratorio de Química Orgánica y Biomolecular, CMN, Universidad Industrial de Santander, Parque Tecnológico Guatiguará, Km 2 Vía Refugio, Piedecuesta 681011, Colombia Email: kouznet@uis.edu.co Email: vkuznechnik@gmail.com

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Abstract

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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 - tetrahydroisoquinoline

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