Spiro Heterocyclic Compounds. V. Synthesis of Spiro [homophthalimide-4,4'-(4'H-pyran)] Compounds

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概要

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• The reaction of 2-methylphthalonimide (1) with malononitrile gave 4-dicyanomethylene-2-methylhomophthalimide (2) in 95% yield. The Michael reaction of 2 with compounds having an active methylene or methyl group (3a-d) afforded the corresponding spiro [2-methylhomophthalimide-4,4'-(4'H-pyran)] compounds (4a-d). In contrast, the reaction of 2 with other active methylene compounds (3e-h) afforded only the same product, spiro [2-methylhomophthalimide-4,1'-(3'-amino-2'-cyano-5', 6'-dihydro-5'-methyl-1'H-pyrano [2,3-c] isoquinolin-6'-one)] (5), which was found to be produced by the reaction of 2 with homophthalimide in quantitative yield. All the latter reactions can be regarded as the results of retrograde Michael reactions between the reactants 2 and active methylenes (3e-h). By refluxing a methanol solution of 2 in the presence of a basic catalyst, the ringtrasformation product, methyl 1-dicyanomethyl-2-methyl-3-oxo-isoindoline-1-carboxylate (8) was obtained in 80% yield.

• 社団法人日本薬学会の論文
• 1982-04-25

著者

• 乙益 寛隆

  Hoshi College of Pharmacy

• 藤巻 照久

  Faculty of Pharmaceutical Sciences, Hoshi University

• 藤巻 照久

  Faculty Of Pharmaceutical Sciences Hoshi University

• 乙益 寛隆

  Faculty Of Pharmaceutical Sciences Hoshi University

• 藤巻 照久

  Hoshi College of Pharmacy

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