Tetrahedron

On the Reaction of Isatin with Cyanomethylene (triphenyl)-phosphorane. A Nucleophilic Attack of Alkyl Phosphites on the Carbon–Carbon Double Bond of (E)- …

FH Osman, FA El-Samahy

Index: Osman, Fayez H.; El-Samahy, Fatma A. Tetrahedron, 2000 , vol. 56, # 13 p. 1863 - 1871

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Citation Number: 26

Abstract

The reaction of cyanomethylene (triphenyl) phosphorane (2) with isatin (1) in dry benzene at room temperature for 1h led to the formation of (1, 2-dihydro-2-oxo-3H-indol-3-yl) acetonitrile as a mixture of E-and Z-stereo isomers 3 and 4. Trialkyl phosphites 7 reacted with (E)-nitrile 3 in dry benzene at 70° C for about 10h to give the phosphonates 8 as two isomers together with the unexpected spiro products of isomers 9. When the (E)-nitrile 3 was allowed to ...