REGIOSPECIFIC SYNTHESIS OF 1,6- DIMETHY L-9,lO-ANTHRACENEDIONE
Treatment of acetyl- 1,4-benzoquinone with isoprene gave the corresponding regioselective adduct (I). Rearrangement of the adduct (1) in pyridine and methanol gave 2-acetyl-5, 8-dihydro-6-methyl- 1,4-dihydroxynaphthalene (2). Silver oxide oxidation of the rearranged product (2) gave 2-acetyl-5,8-dih...
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| Format: | Article |
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| Language: | English |
| Published: |
University of Tehran
1997-09-01
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| Series: | Journal of Sciences, Islamic Republic of Iran |
| Online Access: | https://jsciences.ut.ac.ir/article_31252_63ff1be82cae7709c98cda1cdcb6a90a.pdf |
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| Summary: | Treatment of acetyl- 1,4-benzoquinone with isoprene gave the corresponding
regioselective adduct (I). Rearrangement of the adduct (1) in pyridine and
methanol gave 2-acetyl-5, 8-dihydro-6-methyl- 1,4-dihydroxynaphthalene (2).
Silver oxide oxidation of the rearranged product (2) gave 2-acetyl-5,8-dihydro-
6-methyl- 1,4naphthalenedione (3). Regioselective addition of trans-piperylene
to this compound (3) gave the c&esponding adduct (4). Treatment of the
resulting cycloadduct (4) with manganese dioxide gave the regiospecific 1,6-
dimethyl-9, 10-anthracenedione (5). Each of the foregoing reactions proceeds in
high yield |
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| ISSN: | 1016-1104 2345-6914 |