Reacción #93956

ord-6b95a365086e4e3fa90b5593564ad1c0

Ecuación de reacción

O=C1Nc2ccccc2C1=O
isatin
O=C1Nc2ccccc2C1=O
isatin
Cc1ccc(S(=O)(=O)NN)cc1
p-toluenesulfonylhydrazine
[Na+].[OH-]
sodium hydroxide
[Al+3].[Al+3].[O-2].[O-2].[O-2]
aluminum oxide
→
[N-]=[N+]=C1C(=O)Nc2ccccc21
3-diazoindol-2(3H)-one

Reactantes

O=C1Nc2ccccc2C1=O
isatin
O=C1Nc2ccccc2C1=O
isatin
Cc1ccc(S(=O)(=O)NN)cc1
p-toluenesulfonylhydrazine
—
hydrazone
[Na+].[OH-]
sodium hydroxide
[Al+3].[Al+3].[O-2].[O-2].[O-2]
aluminum oxide

Reactivos

Ninguno

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Otrothe corresponding 3-diazoindol-2(3H)-one is prepared in accordance with known procedures

Procedimiento

Once the desired isatin has been obtained, the corresponding 3-diazoindol-2(3H)-one is prepared in accordance with known procedures. See, for example, J. M. Michowski, Tetrahedron Letters, 1773 (1967) and M. P. Cava, et al., J. Am. Chem. Soc., 80, 2257 (1958). The appropriate isatin compound is treated with p-toluenesulfonylhydrazine. The resulting hydrazone then is treated with a base such as aqueous sodium hydroxide or aluminum oxide to give the desired 3-diazoindol-2(3H)-one.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US04128644uspto-grants-1978_12