1,2,4,5-Tetrazine, 3,6-diphenyl- → 1,4-Diphenyl-5,6,7,8,9,10-hexahydrocycloocta[d]pyridazine

HRID 883518Notes

Reaction equation

HRID 883518 reaction equation
[C:1]1([C:7]2[N:8]=[N:9][C:10]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=NN=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:19]1=[CH:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]1>C1COCC1>[C:13]1([C:10]2[C:26]3[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][C:19]=3[C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)=[N:8][N:9]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 232631,2,4,5-Tetrazine, 3,6-diphenyl-HCID 5463599trans-Cyclooctene

Product 1

HCID 124736261,4-Diphenyl-5,6,7,8,9,10-hexahydrocycloocta[d]pyridazineYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A dry round-bottomed flask was charged with 3,6-diphenyl-1,2,4,5-tetrazine (0.030 g, 0.13 mmol) and the flask was evacuated and filled with nitrogen. Anhydrous THF (1.3 mL) and trans-cyclooctene (0.014 g, 0.21 mmol) were added to the reaction mixture. After approximately 20 minutes the purple solution turned yellow, indicating that the reaction had gone to completion. The reaction mixture was concentrated under reduced pressure. The crude yellow residue was chromatographed on silica gel using a gradient (0-50%) of EtOAc in hexanes as the eluent to give 38 mg (95%) of the title compound as a pale yellow solid, mp 163-165° C. The adduction product had aromatized upon workup and chromatography to provide the titled compound.

Workup

  1. customthe flask was evacuated
  2. additionfilled with nitrogen
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. customThe crude yellow residue was chromatographed on silica gel using a gradient (0-50%) of EtOAc in hexanes as the eluent

Sources & evidence

ORD record
ord-7c620ae870264088a5445a02bcd55295
Source dataset
uspto-grants-2012_08
Patent number
US08236949B2

Reaction notes

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