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Carcinogenic nitrogen compounds. Part LXXV. Skraup reactions with some polycyclic amines, and two cases of anti-Marckwald orientation

1972; Linguagem: Inglês

10.1039/p19720000263

2050-8255

Ng. Ph. Buu‐Hoï, P. Jacquignon, D. C. Thang, T. Bartnik,

Organic and Inorganic Chemical Reactions

12-Halogeno-6-hexanoylaminochrysenes undergo Skraup reactions to give the corresponding 10-substituted benzo[h]naphtho[1,2-f]quinolines, but 6-hexanoylamino-12-nitrochrysene gives benzo[h]benzo[7,8]quino-[6,5-f]quinoline. Benzo[h]naphtho[1,2-f]quinoline undergoes oxidation to an o-quinone, from which several benzo[c]benzo[7,8]quino[6,5-a]phenazines have been prepared. Phenanthro[9,10-g]quinoline and benzo[h]quino[6,7-f]quinoline were obtained from 2-aminotriphenylene and 3-acetamido-9-aminophenanthrene respectively, in two rare examples of anti-Marckwald Skraup cyclisations.