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Synthesis 2020; 52(09): 1425-1434
DOI: 10.1055/s-0037-1610750
DOI: 10.1055/s-0037-1610750
paper
Synthesis of 4-Vinyl-1,2,3,4-tetrahydroisoquinoline from N-Tethered Benzyl-Alkenol Catalyzed by Indium(III) Chloride: Formal Synthesis of (±)-Isocyclocelabenzine
This work was supported by Council of Scientific & Industrial Research (CSIR), New Delhi (grant no. 02(0364)/19/EMR-II).Further Information
Publication History
Received: 20 December 2019
Accepted after revision: 20 January 2020
Publication Date:
12 February 2020 (online)
![](https://www.thieme-connect.de/media/synthesis/202009/lookinside/thumbnails/ss-2019-n0438-op_10-1055_s-0037-1610750-1.jpg)
Abstract
An intramolecular Friedel–Crafts cyclization reaction catalyzed by indium(III) chloride for the formation of 4-vinyl-1,2,3,4-tetrahydroisoquinoline from N-tethered benzyl-alkenol in good yields has been described. The reaction is highly regioselective and generates an exocyclic vinyl functionality in the piperidine ring. The reaction is compatible with a wide range of functional groups. The strategy is demonstrated for the formal synthesis of (±)-isocyclocelabenzine alkaloid.
Key words
tetrahydroisoquinoline - (±)-isocyclocelabenzine - indium(III) chloride - regioselectivity - N-tethered benzyl-alkenol - Friedel–CraftsSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1610750.
- Supporting Information
- CIF File
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The melting point is not available in the reported literature: