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■ Synthesis of Some New Spiro[indoline-3,2'-(1',2',3',4'-tetrahydroquinoline)]-2,4'-dione Derivatives

Marzoog S. Al-Thebeiti

*Department of Chemistry, Faculty of Applied Sciences, Umm Al-Qura University, Makkah Almukkarramah, P. O. Box 6876, Saudi Arabia

Abstract

Indole-2,3-dione (1) was treated with malonic acid in a mixture of ethanol/pyridine to afford 3-(2-oxoindolinylidine)acetic acid (2), which then reacted with hydrobromic acid to yield 3-bromo-3-(2-oxoindol)acetic acid (3). Compound (3) reacted with aromatic amines to yield 3-arylamino-3-(2-oxoindole)acetic acid derivatives (4a-e). Cyclization of compounds (4a-e) with triflic acid afforded spiro[indoline-3’,2’-(1’,2’,3’,4’-tetrahydroquinoline)]-2,4’-dione derivatives (6a-e). Alkylation of compounds (4a-e) with methyl iodide gave 3-arylmethylamino-2-(1-methyl-2-oxoindole)acetic acid derivatives (5a-e). Cyclization of compounds (5a-e) with triflic acid yielded spiro[indoline-3,2’-(1’,2’,3’,4’-tetrahydroquinoline)]-1,1’-dimethyl-2,4’-dione derivatives (7a-e). Also alkylation of compounds (6a-e) with methyl iodide yielded compounds (7a-e).