Cyclohexene → 5,8-Dihydro-6,8-dimethyl-3-phenyl-5,8-ethano-6H-pyrano[4,3-e]-1,2,4-triazine

HRID 895003Notes

Reaction equation

HRID 895003 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

5

Reactant 2

HCID 8079CyclohexeneHCID 12767938HCID 12767938, compound

Product 1

HCID 127679395,8-Dihydro-6,8-dimethyl-3-phenyl-5,8-ethano-6H-pyrano[4,3-e]-1,2,4-triazine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

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.

Workup

  1. temperatureThe resulting mixture is refluxed under a nitrogen atmosphere for 18 hours
  2. customThe catalyst is then removed by filtration
  3. customthe filtrate evaporated

Sources & evidence

ORD record
ord-17fbd40cc50142c99db9de6c239028f8
Source dataset
uspto-grants-1981_08
Patent number
US04285944

Reaction notes

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