Some Derivatives of Benzidine

Cyclization reactions of 2,2'-disubstituted biphenyls

“…An analogous cyclization, with retention of the substituent originally on oxygen, is observed upon heating the diazonium sulfate (CLXV) prepared in situ from 2 '-phenoxy-2-biphenylamine, which gives CLXVa (131a). However, 6,6'-dimethyl-2,2'-diamin-HSOf obiphenyl gives only the corresponding dihydroxy compound and no furan (152), probably because of coplanarity difficulties. Treatment of diazotized 2'methoxy-2-biphenylamine with cuprous chloride in a carbon dioxide atmosphere yields 2-chloro-2 '-methoxybiphenyl ( 113 ring-phenyl insertion product CLXVI was unaffected by the temperature (152).…”

“…However, 6,6'-dimethyl-2,2'-diamin-HSOf obiphenyl gives only the corresponding dihydroxy compound and no furan (152), probably because of coplanarity difficulties. Treatment of diazotized 2'methoxy-2-biphenylamine with cuprous chloride in a carbon dioxide atmosphere yields 2-chloro-2 '-methoxybiphenyl ( 113 ring-phenyl insertion product CLXVI was unaffected by the temperature (152).…”

“…dc> Ao: 0 LX VII LXVIII However, reaction of the tetraacid LXVI with acetyl chloride yields only the dianhydride LXVII and none of the diphenic anhydride LXVIII (94). Hydrolysis of 2-acetamido-2'-biphenylcarboxylic acids yields lactams as products; for example, LXX is formed from LXIX (153) and the bislactam LXXII from LXXI (95).…”

The Chemistry of Cinnolines.

“…Stoermer and Gaus (44) were able to show that with pyridazinedicarboxylic acids, as with pyridinedicarboxylic acids, it is the carboxyl group nearer the nitrogen which is first A few cinnolines are known to give JV-oxides. The N-oxide of benzo[c]cinnoline was obtained by reduction of 2,2'-dinitrobiphenyl with sodium sulfide (17,34,51) or with the calculated amount of sodium amalgam in methanol (47), much as azoxybenzene is obtained from nitrobenzene. Excess sodium amalgam or stannous chloride in hydrochloric acid solution converted the JV-oxide to benzo[c]cinnoline.…”

The Chemistry of Phenanthridine and its Derivatives.

“…(81) nor 9-(p-i v i d u a l n o t d i r e c t l y a s s o c i a t e d w i t h s c i t e i s p r o h i b i t e d .…”