Tetrahedron p. 7763 - 7774 (1992)
Update date:2022-08-04
Topics:
Brown
Coulston
Eastwood
Moffat
Flash vacuum pyrolysis of 2-phenylquinoline-3,4-dicarboxylic anhydride at 800°/0.06 mm gave indeno[1,2-b]indole (30-40%), which readily added nucleophiles Y- at C-10 to give 5,10-dihydro derivatives (Y=H, Me, Ph, NEt2, OMe, CH(COOMe)2 and CMe2NO2). Similar pyrolysis of the 2-benzylquinoline anhydride gave a 1:2 mixture of the (expected) linear 5H-benzo[b]carbazole and the (unexpected) angular 7H-benzo[c]carbazole. The isomeric 2-o-tolylquinoline anhydride on similar pyrolysis gave mainly 11H-benzo[a]carbazole (85%), isomeric benzocarbazoles (4%) and 11H-indeno[1,2-b]quinoline (2.6%). Most of these products are probably derived from exocyclic carbenes formed by aryne-carbene equilibration, but the last compound may be formed by direct aryne-methyl interaction.
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