The Reaction of Isatin with Alkoxycarbonylmethylene (Triphenyl)Phosphoranes

Abstract

Isatin (1) reacted with alkoxycarbonylmethylene(triphenyl)phosphoranes (2) in boiling benzene for about 3 h to give orange yellow crystalline products of alkyl (1,2-dihydro-2-oxo-3H-indol-3-yl)acetates (3). The double bond of compounds 3 was reduced with zinc dust in boiling acetic acid to give 5, which upon methylation with methyl iodide in dry acetone and anhydrous potassium carbonate yielded the corresponding products 6. The structural assignments of the new compounds are based on the spectroscopic results.

Keywords::

• Isatin
• Wittig reaction
• NMR spectra (¹H; ¹³C)