Synthesis of 4-Vinyl-1,2,3,4-tetrahydroisoquinoline from N-Tethered Benzyl-Alkenol Catalyzed by Indium(III) Chloride: Formal Synthesis of (±)-Isocyclocelabenzine
| Autor: | Bipin Kumar Behera, Ngangbam Renubala Devi, Sudip Shit, Anil K. Saikia |
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| Rok vydání: | 2020 |
| Předmět: |
010405 organic chemistry
Tetrahydroisoquinoline Organic Chemistry Regioselectivity 010402 general chemistry 01 natural sciences Chloride Medicinal chemistry Catalysis 0104 chemical sciences chemistry.chemical_compound chemistry Intramolecular force medicine Indium(III) chloride Piperidine Friedel–Crafts reaction medicine.drug |
| Zdroj: | Synthesis. 52:1425-1434 |
| ISSN: | 1437-210X 0039-7881 |
| DOI: | 10.1055/s-0037-1610750 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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