The reaction of 2-arylsulfonyloxytropones and active methylene compounds The formation of 8-hydroxy-2H-cyclohepta[b]furan-2-one and 2-amino-8H-cyclohepta[b]furan-8-one derivatives |
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Authors: | T. Nozoe K. Takase M. Kato T. Nogi |
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Affiliation: | Department of Chemistry, Faculty of Science, Tohoku University, Katahira-2-chome, Sendai, Japan |
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Abstract: | Reaction of 2-arylsulfonyloxytropones (IV) and active methylene compounds, diethyl malonate, ethyl acetoacetate, ethyl cyanoacetate, malononitrile or cyanoacetamide, in the presence of NaOEt give 8-hydroxy-2H-cyclohepta[b]furan-2-one derivatives (V) and/or 2-amino-8H-cyclohepta[b]furan-8-one derivatives (VII), in addition to azulene derivatives (1) or 2H-cyclohepta(b]furan-2-one derivatives (II), known to be obtained by the reaction of 2-chlorotropones or 2-methoxytropones with active methylene compounds. Relative yields of products are influenced markedly by conditions, e.g. base type or molar ratios. The formation of V and VII is characteristic of 2-arylsulfonyloxytropones, not being observed with 2-chlorotropones or 2-methoxytropones. A reaction course involving elimination of the arylsulfonyl group as arenesulfinate ion is presented. |
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