Compound 2a

Methyl 2-(1-acetyl-2-oxoindolin-3-ylidene)acetate

From: Construction of bispirooxindoles containing three quaternary stereocentres in a cascade using a single multifunctional organocatalyst

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InChIKey ASWBFUSHNDQBPA-JXMROGBWSA-N

Synonyms:
  • Methyl (2E)-(1-acetyl-2-oxo-1,2-dihydro-3H-indol-3-ylidene)acetate,
  • acetic acid, (1-acetyl-1,2-dihydro-2-oxo-3H-indol-3-ylidene)-, methyl ester, (2E)-,
  • methyl 2-(1-acetyl-2-oxobenzo[d]azolin-3-ylidene)acetate,
  • (1-Acetyl-2-oxo-1,2-dihydro-indol-3-ylidene)-acetic acid methyl ester

Synthetic procedure: See article for the definitive version of this procedure and for full experimental details.

Wittig reagent (2 mmol, 1 equiv) was added to a solution of the acetyl isatin (2.4 mmol, 1.2 equiv) in CHCl3 or DCM (5 mL) in a 25 mL round bottom flask. The solution was stirred at rt for 30 min. The mixture was purified by flash chromatography to yield the desired products 2a around 60% yields. 1H-NMR (500MHz, CDCl3): δ 8.68 (d, J = 8.0 Hz, 1H), 8.29 (d, J = 8.0 Hz, 1H), 7.45 (t, J = 7.5, 1H), 7.26-7.23 (m, 1H), 6.94 (s, 1H), 3.91 (s, 3H), 2.71 (s, 3H). 13C-NMR (125 MHz, CDCl3): δ 170.27, 167.85, 165.58, 142.15, 136.50, 132.98, 128.14, 125.36, 122.80, 120.33, 116.42, 52.33, 26.82. HRMS (ESI) calcd for [M+H] C13H12NO4, m/z: 246.0761, observed: 246.0767.

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