Heterocyclic analogs of pleiadiene:: LXXIV.: peri-cyclizations in the perimidine series.: Synthesis of 1,3-diazapyrene derivatives

Reactions of perimidines and perimidin-2-ones with alpha,beta-unsaturated carbonyl compounds gave various 1,3-diazapyrene derivatives. Acylation of 1-methylperimidine, perimidin-2-one, and 1-methylperimidin-2-one with cinnamoyl chloride in the presence of AlBr3 is accompanied by peri-fusion at the 6,7-position and dearylation of the intermediate product. Under analogous conditions, 1,3-dimethyl-2,3-dihydroperimidine gave rise to 6-cinnamoyl-1,3-dimethyl-2,3-dihydroperimidine. Reactions of perimidin-2-ones with 1,3-diphenyl-2-propenone in polyphosphoric acid resulted in peri-fusion at the 6,7-position, and with acetylacetone, at the 1,9-position.