Synthesis of substituted 3-arylpiperidines and 3-arylpyrrolidines by radical 1,4 and 1,2-aryl migrations
| Autor: | Samir Z. Zard, Beatrice Quiclet‐Sire, Alexandru Gheorghe, Xavier Vila |
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| Přispěvatelé: | Laboratoire de synthèse organique (DCSO), École polytechnique (X)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS) |
| Rok vydání: | 2007 |
| Předmět: |
[CHIM.ORGA]Chemical Sciences/Organic chemistry
010405 organic chemistry Chemistry Sodium cyanoborohydride Aryl Organic Chemistry General Medicine 010402 general chemistry 01 natural sciences Biochemistry Medicinal chemistry 0104 chemical sciences chemistry.chemical_compound Hydrolysis Ammonia Acetylation Drug Discovery Organic chemistry Amine gas treating Piperidine Xanthate ComputingMilieux_MISCELLANEOUS |
| Zdroj: | Tetrahedron Tetrahedron, Elsevier, 2007, 63 (30), pp.7187-7212. ⟨10.1016/j.tet.2007.04.091⟩ |
| ISSN: | 0040-4020 |
| DOI: | 10.1016/j.tet.2007.04.091 |
| Popis: | A route to 3-arylpiperidines and 3-arylpyrrolidines involving radical 1,4- and 1,2-aryl migrations has been explored. For the piperidines, the first route requires a xanthate addition to an N-allylarylsulfonamide, followed by acetylation and treatment with lauroyl peroxide to give the corresponding 1,4-aryl transfer product. This compound can be converted into the desired piperidine derivative following acidic hydrolysis. For the second approach to piperidines, addition of an α-keto xanthate to olefins of type 14 causes 1,2-aryl migration leading to an α,β-unsaturated ester, which can be converted into a piperidine by the action of ammonia or a primary amine and sodium cyanoborohydride. Substituted 3-arylpyrrolidines can be obtained by simply starting with an α-amido substituted xanthate. |
| Databáze: | OpenAIRE |
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