Spiro Heterocyclic Compound. II. Synthesis of Spiro [indoline-3,3'-(5'-pyrazolin)]-2-ones and Related Compounds

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概要

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• A spiro-heterocyclate, pyrazole-ring combined at the position-3 of indolin-2-ones was examined. 3-Phenacylideneindolin-2-ones (Ia-d) reacted with hydrazine hydrate to give the corresponding spiro [indoline-3,3'-(5'-pyrazolin)]-2-ones (IIa-d). The reaction of 3-phen-acylidene-(Ia) and 3-acetonylideneindolin-2-one (If) with diazomethane afforded 4' benzoyl-(Va) and 4'-acetyl-spiro [indoline-3,3'-(1'-pyrazolin)]-2-one (Vb), respectively. The decomposition of 1-pyrazolines (Va-b) by thermolysis or by reacting with HCI gave spiro [cyclopropane-1,3'-indolin]-2'-ones (VIa and VIb), whereas during chromatography on alumina changed into 3-(α-benzoyl)-(VIIa) and 3-(α-acetyl) ethylideneindolin-2-one (VIIb), respectively. In addition, 3-(α-nitro) ethylideneindolin-2-one (VIII) reacted with diazomethane to give 1,4'-dimethyl-4'-nitro-spiro [indoline-3,3'-(1'-pyrazolin)]-2-one (IX), which being chromatographed on alumina gave 1,4'-dimethyl-spiro [indoline-3,3'-(3'H-pyrazol)]-2-one (X).

• 公益社団法人日本薬学会の論文
• 1976-04-25

著者

• 乙益 寛隆

  Hoshi College of Pharmacy

• 乙益 寛隆

  Faculty Of Pharmaceutical Sciences Hoshi University

• 青柳 みどり

  Hoshi College Of Pharmacy

• 田中 多枝

  Hoshi College of Pharmacy

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