Reaktion #93956

ord-6b95a365086e4e3fa90b5593564ad1c0

Reaktionsgleichung

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

Edukte

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

Reagenzien

Keine

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

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

Vorschrift

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.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US04128644uspto-grants-1978_12