Cyclohexene → 3-phenyl-5,8-dihydro-6,8-dimethyl-5,8-ethano-6H-pyrano[4,3-e]-as-triazine

Reaction equation

[C:1]1([C:7]2[N:8]=[N:9][C:10]3[C:17]4([CH3:20])[CH2:18][CH2:19][CH:14]([CH:15]([CH3:21])[O:16]4)[C:11]=3[N+:12]=2[O-])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1CCCCC=1>[Pd].C(O)C>[C:1]1([C:7]2[N:8]=[N:9][C:10]3[C:17]4([CH3:20])[CH2:18][CH2:19][CH:14]([CH:15]([CH3:21])[O:16]4)[C:11]=3[N:12]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

Procedure

To a solution of 1.66 g. (0.006 mole) 3-phenyl-5,8-dihydro-6,8-dimethyl-5,8-ethano-6H-pyrano[4,3-e]-as-triazine-4-oxide and 1.50 g. (0.018 mole) cyclohexene in 30 ml. absolute ethanol there is added 60 mg. 10% palladium on charcoal. The resulting mixture is refluxed under a nitrogen atmosphere for 18 hours. The catalyst is then removed by filtration and the filtrate evaporated to give 3-phenyl-5,8-dihydro-6,8-dimethyl-5,8-ethano-6H-pyrano[4,3-e]-as-triazine.