Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
Synthesis of Polycyclines. I. Diels-Alder Reaction of 5-Nitronaphthoquinone with Unsymmetrical Butadienes
織田 範一小林 和弘植田 泰誠伊藤 磯雄
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キーワード: aromatization
ジャーナル フリー

1978 年 26 巻 8 号 p. 2578-2581

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抄録
Diels-Alder reaction of 5-nitro-1, 4-naphthoquinone (1) and unsymmetrical butadienes was carried out. Reaction of 1 and 2-methyl-1, 3-butadiene gave 1, 4, 4a, 9a-tetrahydro-2-methyl-5-nitro-anthraquinone (2) and its 3-methyl analogue (3) at the ratio of 9.2 : 1. Reaction of 1 and 1, 3-pentadiene gave 1, 4, 4a, 9a-tetrahydro-1-methyl-8-nitroanthraquinone (8) and its 5-nitro analogue (9) at the ratio of 10 : 7. Their structures have been determined by aromatization to methyl-nitroanthraquinones.
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© The Pharmaceutical Society of Japan
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