JV-Nitrosodiphenylamine

Indolizines are readily nitrosated in the 1- or 3-position by the action of nitrous acid -182 or jV-nitrosodiphenylamine.183 The nitroso derivatives 114 and 115 have been shown to oxidize l-hydroxy-2-phenylin-... 

Two syntheses of benzocinnoline Ar-imines have been described recently.78 They can be prepared from benzocinnoline and hydroxy lamine-O-sulfonic acid or by diazotization of 2,2 -diaminobiphenyl with pentyl nitrite or JV-nitrosodiphenylamine. Diazotization of the diamine presumably proceeds via the triazepine 48, which is isomeric with unsubstituted benzocinnoline iV-imine. Benzocinnoline iV-imine itself, the only unsubstituted iV-imine so far isolated, was prepared from benzocinnoline and hydroxylamine-O-sulfonic acid. Under similar conditions, quaternary IV-amino salts were isolated from the other iV-heterocycles. The unsubstituted Ar-imine can be converted easily into the acyl, sulfonyl, and 2,4-dinitrophenyl derivatives (Scheme 3). 

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