The Fischer indolisation reaction and the synthesis of dihydroindenoindoles

Article abstract of DOI:10.1016/S0040-4020(01)81911-6

The Fischer reaction between indanones and certain alkoxyarylhydrazines fails; the indanones are returned unreacted and the arylhydrazines are converted into the corresponding alkoxy-2-chloroarylamines and other products.A new N-amination route to arylhydrazines from the arylamines has been developed and it has been demonstrated that problems with the indolisation of alkoxyarylhydrazones can be circumvented by ring closures of their O-tosylated analogues.Some results using the Lepke synthesis of indoles are recorded.