Spiro Heterocyclic Compounds. IV. Synthesis of Spiro [oxindole-3,4'-(2', 3'-dihydro-4'H-pyran)] and Spiro [oxindole-3,4'-(1', 4'-dihydropyridine)] Compounds

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概要

• 論文の詳細を見る

• The Michael reaction of 3-(carboethoxy-cyano) methyleneoxindole (Ia) or 3-dicyanomethyleneoxindole (Ib) with active methyl groups, e.g., acetophenone and acetone, afforded, the corresponding normal Michael adducts (IIa-c). The reduction of IIa with NaBH_4 gave the spiro [oxindole-3,4'-(2', 3'-dihydro-4'H-pyran)] compound (III), which on reaction with diazomethane afforded two methoxy derivatives (IVa, b) diastereomeric at C-2' of the 2', 3'-dihydropyran ring. The reduction of IIb, c with NaBH_4 gave similar spiro compounds (V-VI), which gave similar diastereoisomers, Va, b and VIa, b, respectively. Refluxing of IIc with NH_2OH gave the spiro [oxindole-3,4'-(1', 4'-dihydropyridine)] compound (X). When the same reaction was carried out at 0°, compound (IX), the precursor of X, was obtained.

• 社団法人日本薬学会の論文
• 1980-05-25

著者

• 乙益 寛隆

  Hoshi College of Pharmacy

• 乙益 寛隆

  Faculty Of Pharmaceutical Sciences Hoshi University

• 東山 公男

  星薬科大学

• 東山 公男

  Hoshi College of Pharmacy

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