A one-step conversion of isoquinolinium salts into naphthalene derivatives1 |
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Authors: | M. Shamma J.L. Moniot L.A. Smeltz W.A. Shores L. Töke |
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Affiliation: | Department of Chemistry, The Pennsylvania State University, University Park, Pennsylvania 16802, U.S.A. |
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Abstract: | Berberine chloride (1) upon treatment with NaOAc-Ac2O yields naphthalene derivatives 4 and 5 In like fashion, 8 gives naphthalene 10; isoquinoline methiodide leads to β-naphthyl acetate; and 12 provides 14. The reaction has been extended to the 3-carbonyl pyridinium series where 3-acetylpyridine methiodide and 3-pyridinecarboxaldehyde methiodide furnish lactones 16 and 17, respectively. All these transformations proceed by initial nucleophilic attack of the acetic anhydride anion on the immonium carbon atom. |
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Keywords: | Permanent address Department of Organic Chemical Technology, Technical University, 1111 Budapest, Hungary. |
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