Benzo azonine

Palladium-catalyzed heteroannulation is illustrated by synthesis of substituted l//-benzo[rf]azonine 227, which was prepared from allene and tosylamide-containing aryl halide (Equation 26). The reaction was suggested to proceed by addition of an arylpalladium compound to the allene to generate a 7i-allylpalladium intermediate, which subsequently undergoes nucleophilic displacement of palladium at the less-hindered end of the 7i-allyl system <1998JOC6859>. 

Dihydro-llH-benzo[a]carbazole oxidized with periodate according to Synth. Meth. 21, 182 ll,12-dihydro-5H-dibenz[b,g]azonine-6,13-dione (Y 85%) dissolved in 2 N NaOH, allowed to stand at room temp, overnight, and the resulting crude 4-quinolone refluxed 5 hrs. with PCI5 in POCI3 10-chloro-llH-indeno-[l,2-b]quinoline (Y 77%) hydrogenated 2 hrs. with 10%-Pd-on-carbon in methanol llH-indeno[l,2-b]quinoline (Y 91%). F. e. s. J. A. Beisler, J. Med. Chem. 14, 1116 (1971). 

---