Spiro Heterocyclic Compounds. VI. Synthesis of Spiro [imidazolidine-4,1'-isoindoline] and Related Compounds

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概要

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• Nitrosation of 2-methylisoquinoline-1,3 (2H, 4H)-dione (I) with NaNO_2 in AcOH afforded the 4-nitroso compound (II) in almost quantitative yield. Catalytic reduction of II produced 4-imino-2-methylisoquinoline-1,3 (2H, 4H)-dione (III) and a small amount of 4,4'-bi-2-methylisoquinoline-1,3 (2H, 4H)-dione (IV). Acidic hydrolysis of III gave 2-methylisoquinoline-1,3,4 (2H)-trione (V). The hydrogenated mixture of II was allowed to react with methyl- and phenylisocyanate under an inert atmosphere to give 4-ureido compounds (VIIa, b) in yields of 79% (both). Dehydrogenation of VIIa, b with Pd-C afforded the 4-carbamoylimino compounds (VIIIa, b) in 60 and 87% yields, respectively. When their methanol solutions were refluxed with base catalyst, the compounds (VIIIa, b) were transformed into spiro [imidazolidin-4,1'-isoindoline]-2,3', 5-triones (XIIa, b) in yields of 80 and 86%, respectively.

• 社団法人日本薬学会の論文
• 1982-09-25

著者

• 乙益 寛隆

  Hoshi College of Pharmacy

• 乙益 寛隆

  Faculty Of Pharmaceutical Sciences Hoshi University

• 田原 幸代

  Hoshi College of Pharmacy

• 重綱 真理

  Hoshi College of Pharmacy

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