Synthesis of cis-3,4-diarylpiperidines and cis-3,4-diaryltetrahydropyrans |
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Authors: | Meng-Yang Chang Chun-Yu Lin |
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Institution: | a Department of Applied Chemistry, National University of Kaohsiung, No. 700, Kaohsiung University Rd., Kaohsiung 811, Taiwan b Department of Chemistry, National Sun Yat-Sen University, Kaohsiung 804, Taiwan |
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Abstract: | Substituted cis-3,4-diarylpiperidines and cis-3,4-diaryltetrahydropyrans are synthesized in modest overall yields starting from 4-aryl-1,2,5,6-tetrahydropyridines and 4-aryl-1,2,5,6-tetrahydropyrans via the following sequence: (1) pinacol-type ring contraction having the combination of m-chloroperoxybenzoic acid and boron trifluoride etherate, (2) Grignard addition with arylmagnesium bromide reagents and followed by boron trifluoride etherate-mediated intramolecular ring-expanded rearrangement, and (3) hydrogenation with hydrogen on 10% palladium-activated carbon. A facile synthesis of 3,4-diarylpyridines was also described by base-induced aromatization. |
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Keywords: | m-Chloroperoxybenzoic acid Boron trifluoride etherate cis-3 4-Diarylpiperidines cis-3 4-Diaryltetrahydropyrans 3 4-Diarylpyridines |
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