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• W2093669079 abstract "4,5-Dihydro-3H-naphtho[1,8-bc]furans 4 and 6 which have various substituents (R1 and R2) have been synthesized from 8-oxo-5,6,7,8-tetrahydro-1-naphthyloxyacetic acids 1 and 3 or their ethyl esters 2. The reaction of acids 1 and 3 with sodium acetate in acetic anhydride gave a mixture of furans 4 and 6 and lactones 5 and 7. The ratios of the products were varied according to the types of substituents (R1 and R2) in acids 1 and 3. As the substituent R1 (R2 = hydrogen) in acids 1 was changed from hydrogen to a methyl, ethyl or isopropyl group, production of furans 4 became more difficult. However, when a phenyl group was used as the substituent, furan 4 was obtained in good yield. Similarly, as the substituent R2 (R1 = hydrogen) in acids 1 was changed from hydrogen to a methyl, ethyl or isopropyl group, furan formation was more difficult. In contrast, acids 3 which had electron-withdrawing substituents such as chlorine, bromine or a nitro group at the 4-position afforded furans 6 in good yield. 4,5-Dihydro-3H-naphtho[1,8-bc]furans 4 and 4,5-dihydro-3H-naphtho[1,8-bc]furan-2-carbocylic acids 8 were synthesized from the reaction of esters 2 and potassium hydroxide in dioxane. When the substituents R1 or R2 in esters 2 were varied from hydrogen to a methyl, ethyl or isopropyl group the total yields of furans 4 and furancarboxylic acids 8 were reduced." @default.
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• W2093669079 date "1986-05-01" @default.
• W2093669079 modified "2023-09-26" @default.
• W2093669079 title "Furan derivatives. Part8On substituent effects in the synthesis of 4,5-dihydro-3H-naphtho[1,8-bc]furans" @default.
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• W2093669079 doi "https://doi.org/10.1002/jhet.5570230304" @default.
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