109606-75-9Relevant articles and documents
Studies on Intramolecular NH-Bridging in Aromatic Compounds.
Horaguchi, Takaaki,Klemm, L. H.,Norris, Eric S.
, p. 797 - 802 (2007/10/03)
A study was made of the use of calcium oxide as a catalyst at a temperature of 400 - 700 deg for the dehydrocyclization of four primary arylamines: 2-aminobiphenyl, 1-aminotriphenylene (5c), 2-phenoxyaniline, and N-(2-aminophenyl)pyrrole.Maximal yields of cyclized products isolated were 53percent (carbazole), 52percent (4H-naphthocarbazole), 18percent (phenoxazine), and 0percent, respectively.Comparison is made with reported cyclizations of the corresponding nitro and azido starting materials.In one case, treatment of 1-nitrotriphenylene with triethyl phosphite produced mainly diethyl N-(1-triphenylenyl)phosphoramidate (51percent).Mono- and hemihydrochlorides of 5c are described.A mechanism for the catalyzed dehydrocyclization is proposed.