3-Pyridinecarboxaldehyde → 10-(3-pyridylmethylene)-5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one

HRID 1290757Notes

Reaction equation

HRID 1290757 reaction equation
O1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]=[C:7]1[C:19]2[N:18]3[CH:20]=[CH:21][N:22]=[C:17]3[C:16](=[O:23])[NH:15][C:14]=2[C:13]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]1=2.C1N2C3CC4C=CC=CC=4C=3NC(=O)C2=[N:26][CH:25]=1.[H-].[Na+].N1C=CC=C(C=O)C=1>CS(C)=O>[N:26]1[CH:5]=[CH:4][CH:3]=[C:2]([CH:6]=[C:7]2[C:19]3[N:18]4[CH:20]=[CH:21][N:22]=[C:17]4[C:16](=[O:23])[NH:15][C:14]=3[C:13]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]2=3)[CH:25]=1

Participants

6

Reactant 4

HCID 103713-PyridinecarboxaldehydeHCID 24758Sodium hydrideHCID 103535495H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-oneHCID 7034377510-(2-furylmethylene)-5H,10H-imidazo[l,2-a]indeno[1,2-e]pyrazin-4-one

Product 1

HCID 5728636210-(3-pyridylmethylene)-5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

The procedure is performed as in Example 17 for the preparation of 10-(2-furylmethylene)-5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one, but starting with 3 g of 5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one, 60 ml of dimethyl sulphoxide, 0.96 g of sodium hydride and 1.6 g of 3-pyridinecarboxaldehyde. 1.38 g of 10-(3-pyridylmethylene)-5H,10H-imidazo[1,2-a]indeno-[1,2-e]pyrazin-4-one are obtained, in the form of a yellow-orange solid melting above 260° C. (Analysis % calculated C: 73.07, H: 3.87, N: 17.94, O: 5.12, % found C: 73.1, H: 3.9, N: 17.9, O: 5.1).

Sources & evidence

ORD record
ord-1e54d1430f2943fea3cdca9ba178ac6a
Source dataset
uspto-grants-1998_05
Patent number
US05753657

Reaction notes

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