Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
Studies on the Reactions of Heterocyclic Compounds. X. 1, 3-Dipolar Cycloaddition Reaction of Isoquinolinium Ylides and Dicyanoacetylene
小林 義郎熊懐 稜丸関根 安男久津間 輝雄
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1973 年 21 巻 5 号 p. 1118-1123

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The 1, 3-dipolar cycloaddition of dicyanoacetylene (IIb) to isoquinolinium ylides did not give the primary adduct but the aromatized and/or isomerized products. Further, in the reaction of isoquinolinium bis(methoxycarbonyl)methylide (Ia), possibly a rearranged addition product, 1, 10b-dihydropyrrolo[2, 1-α]isoquinoline (VII), was obtained beside 2, 3-dihydropyrrolo[2, 1-α]isoquinoline (Va) and pyrrolo[2, 1-α]isoquinoline (VIa). In the reaction of isoquinolinium cyano(methoxycarbonyl)methylide (Ib), 2, 3-dihydropyrrolo[2, 1-α]isoquinoline (VIII), formed by the liberation of a methoxycarbonyl group, was obtained in addition to VIa and pyrrolo[2, 1-α]isoquinoline-1, 2, 3-tricarbonitrile (VIb).
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© The Pharmaceutical Society of Japan
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