| Budget Amount *help |
¥18,200,000 (Direct Cost: ¥14,000,000、Indirect Cost: ¥4,200,000)
Fiscal Year 2018: ¥3,900,000 (Direct Cost: ¥3,000,000、Indirect Cost: ¥900,000)
Fiscal Year 2017: ¥4,290,000 (Direct Cost: ¥3,300,000、Indirect Cost: ¥990,000)
Fiscal Year 2016: ¥10,010,000 (Direct Cost: ¥7,700,000、Indirect Cost: ¥2,310,000)
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| Outline of Final Research Achievements |
Fluorinated isobenzofurans are considered to be promising building blocks for the synthesis of fluorine-containing carbocyclic and heterocyclic systems. We have developed a novel method for the generation of trifluoromethylated isobenzofurans. The cascade trifluoromethylation/intramolecular acetalization of o-phthalaldehyde proceeded smoothly to give the lactol in high yield. The lactol easily underwent dehydration under acidic conditions to generate trifluoromethylated isobenzofuran, which underwent the intermolecular Diels-Alder reactions with alkenes to give the adducts in good yields. The resultant bicyclo compounds are good precursors of functionalized 1-trifluoromethylnaphthalenes. For instance, [4+2] cycloaddition with naphthpquinone and the subsequent transformations gave trifluoromethylated tetracene. We have obtained several interesting products by the [4+2] cycloaddition of trifluoromethylated isobenzofuran with 1,4-benzoquinone and acenaphthylene.
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