Studies on Tellurium-Containing Heterocycles. Part 20. Reactions of 2-Benzoselenopyrylium Salts and 2-Benzotelluropyrylium Salts with Nucleophiles : Formation of 1-Functionalized 1H-Isoselenochronienes and 1H-Isotellurochromenes

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概要

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• The reactions of the 2-benzoselenopyrylium (1A) and 2-benzotelluropyrylium cations (1B) with a variety of nucleophiles have been investigated. LiAlH_4, sodium alkoxide (NaOMe, NaOi-Pr and NaOt-Bu), diethylamine, n-butylamine and acetone reacted with 1 to give the 1H-isochromenes (2) and the corresponding 1-substituted products (4-9) under mild conditions in almost good to high yields. The 1-alkyl(phenyl)isoselenochromenes (10-13) and 1-benzylisochromenes (18A, 18B), which were produced by the reaction of the salts 1 with Grignard reagents, were converted to the corresponding 1,3-disubstitutecl 2-benzopyrylium salts (14-17, 19) by treatment with triphenylcarbenium tetrafluoroborate (Ph_3C^+ BF^-_4), respectively. The 1-benzylselenopyrylium salts (19A) and l-benzyltelluropyrylium salts (19B) exist in the solvent ais an equilibrium mixture of the salts (19) and the corresponding (Z)-benzylidene compounds (20).

• 公益社団法人日本薬学会の論文
• 2004-01-01

著者

• Sashida Haruki

  Faculty Of Pharmaceutical Sciences Hokuriku University

• OHYANAGI Kazuo

  Faculty of Pharmaceutical Sciences, Hokuriku University

• Ohyanagi Kazuo

  Faculty Of Pharmaceutical Sciences Hokuriku University

関連論文

• Studies on Tellurium-Containing Heterocycles. Part 20. Reactions of 2-Benzoselenopyrylium Salts and 2-Benzotelluropyrylium Salts with Nucleophiles : Formation of 1-Functionalized 1H-Isoselenochronienes and 1H-Isotellurochromenes
• Studies on Tellurium-Containing Heterocycles. Part 22. Tellurazepine Ring System : Preparation of 1,5-Benzotellurazepin-4-ones and Their Conversion into Fully Unsaturated 1,5-Benzotellurazepines
• An Alternative Convenient Synthesis of Piperidazine-3-carboxylic Acid Derivatives
• Ruthenium tetroxide oxidation of N,N'-diBochexahydropyridazines
• An Efficient Transformation of Cyclic Ene-carbamates into ω-(N-Formylamino) carboxylic Acids by Ruthenium Tetroxide Oxidation
• Reactions of 2-Benzoselenopyrylium Salts with Hydrazine : A New Easy Access to 5H-2,3-Benzodiazepines
• Thermal Ring Expansion of 2-Azidoselenochromenes : First Synthetic Examples of 1, 3-Benzoselenazepines

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