(E)-4-AMINOPENT-3-EN-2-ONE

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 7-azido-2-[(4-nitrophenyl)methylene]-3-oxoheptanoic acid 2-cyanoethyl ester (1.12 g, 3.00 mmol) and 4-amino-3-penten-2-one (330 mg, 3.30 mmol) in 20 ml of EtOH was refluxed for 48 hrs. After the EtOH was removed in vacuo, the residue was dissolved in 150 ml of CHCl3, washed with water (2×100 ml) and dried over Na2SO4. After filtration and evaporation of solvent, the product was purified by chromatography (SiO2, CHCl3:MeOH=5:95). 5-Acetyl-2-(4-azidobutyl)-3-(2-cyanoethoxy)carbonyl-1,4-dihydro-6-methyl-4-(4-nitrophenyl)pyridine was obtain as a yellow oil (1.05 g, 77% yield). After the EtOH was removed in vacuo the residue was dissolved in 150 ml of CHCl3 washed with water (2×100 ml) dried over Na2SO4 After filtration and evaporation of solvent the product was purified by chromatography (SiO2, CHCl3:MeOH=5:95)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 7-azido-2-[(4-nitrophenyl)methylene]-3-oxoheptanoic acid 2-cyanoethyl ester (1.12 g, 3.00 mmol) and 4-amino-3-penten-2-one (330 mg, 3.30 mmol) in 20 ml of EtOH was refluxed for 48 hrs. After the EtOH was removed in vacuo, the residue was dissolved in 150 ml of CHCl3, washed with water (2×100 ml) and dried over Na2SO4. After filtration and evaporation of solvent, the product was purified by chromatography (SiO2, CHCl3:MeOH=5:95). 5-Acetyl-2-(4-azidobutyl)-3-(2-cyanoethoxy)carbonyl-1,4-dihydro-6-methyl-4-(4-nitrophenyl)pyridine was obtain as a yellow oil (1.05 g, 77% yield). After the EtOH was removed in vacuo the residue was dissolved in 150 ml of CHCl3 washed with water (2×100 ml) dried over Na2SO4 After filtration and evaporation of solvent the product was purified by chromatography (SiO2, CHCl3:MeOH=5:95)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 7-azido-2-[(4-nitrophenyl)methylene]-3-oxoheptanoic acid 2-cyanoethyl ester (1.12 g, 3.00 mmol) and 4-amino-3-penten-2-one (330 mg, 3.30 mmol) in 20 ml of EtOH was refluxed for 48 hrs. After the EtOH was removed in vacuo, the residue was dissolved in 150 ml of CHCl3, washed with water (2×100 ml) and dried over Na2SO4. After filtration and evaporation of solvent, the product was purified by chromatography (SiO2, CHCl3:MeOH=5:95). 5-Acetyl-2-(4-azidobutyl)-3-(2-cyanoethoxy) carbonyl-1,4-dihydro-6-methyl-4-(4-nitrophenyl) pyridine was obtain as a yellow oil (1.05 g, 77% yield). After the EtOH was removed in vacuo the residue was dissolved in 150 ml of CHCl3 washed with water (2×100 ml) dried over Na2SO4 After filtration and evaporation of solvent the product was purified by chromatography (SiO2, CHCl3:MeOH=5:95)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 5.64 g (40 mmol) of 4-chlorobenzaldehyde, 4.0 g (40 mmol) of 4-aminopent-3-en-2-one and 4.6 g (40 mmol) of methyl acetoacetate are heated to reflux for 12 h in 100 ml of isopropanol. The reaction mixture is allowed to cool and is concentrated. 1.85 g of the title compound crystallize from Et2O. to cool is concentrated 1.85 g of the title compound crystallize from Et2O

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 5.64 g (40 mmol) of 4-chlorobenzaldehyde, 4.0 g (40 mmol) of 4-aminopent-3-en-2-one and 4.6 g (40 mmol) of methyl acetoacetate are heated to reflux for 12 h in 100 ml of isopropanol. The reaction mixture is allowed to cool and is concentrated. 1.85 g of the title compound crystallize from Et2O. to cool is concentrated 1.85 g of the title compound crystallize from Et2O

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A stirred solution of 0.53 g of 5-acetonyl-3-chloromethyl-1,2,4-oxadiazole, 0.46 g of 3-nitrobenzaldehyde and 0.30 g of 2-amino-4-oxo-2-pentene in 4 ml of isopropyl alcohol was heated under reflux for 14 hours. The reaction mixture was concentrated in vacuo and the residue was chromatographed on silica gel using benzene-acetonitrile (15:1) as eluent to give 0.79 g of 5-acetyl-1,4-dihydro-2,6-dimethyl-3-(3-chloromethyl-1,2,4-oxadiazol-5-yl)-4-(3-nitrophenyl)pyridine. under reflux for 14 hours The reaction mixture was concentrated in vacuo the residue was chromatographed on silica gel

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A stirred solution of 0.53 g of 5-acetonyl-3-chloromethyl-1,2,4-oxadiazole, 0.46 g of 3-nitrobenzaldehyde and 0.30 g of 2-amino-4-oxo-2-pentene in 4 ml of isopropyl alcohol was heated under reflux for 14 hours. The reaction mixture was concentrated in vacuo and the residue was chromatographed on silica gel using benzene-acetonitrile (15:1) as eluent to give 0.79 g of 5-acetyl-1,4-dihydro-2,6-dimethyl-3-(3-chloromethyl-1,2,4-oxadiazol-5-yl)-4-(3-nitrophenyl)pyridine. under reflux for 14 hours The reaction mixture was concentrated in vacuo the residue was chromatographed on silica gel

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 7-azido-2-[(4-nitrophenyl)methylene]-3-oxoheptanoic acid 2-cyanoethyl ester (1.12 g, 3.00 mmol) and 4-amino-3-penten-2-one (330 mg, 3.30 mmol) in 20 ml of EtOH was refluxed for 48 hrs. After the EtOH was removed in vacuo, the residue was dissolved in 150 ml of CHCl3, washed with water (2×100 ml) and dried over Na2SO4. After filtration and evaporation of solvent, the product was purified by chromatography (SiO2, CHCl3 :MeOH=5:95). 5-Acetyl-2-(4-azidobutyl)-3-(2-cyanoethoxy)carbonyl-1,4-dihydro-6-methyl-4-(4-nitrophenyl)pyridine was obtain as a yellow oil (1.05 g, 77% yield). After the EtOH was removed in vacuo the residue was dissolved in 150 ml of CHCl3 washed with water (2×100 ml) dried over Na2SO4 After filtration and evaporation of solvent the product was purified by chromatography (SiO2, CHCl3 :MeOH=5:95)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 7-azido-2-[(4-nitrophenyl)methylene]-3-oxoheptanoic acid 2-cyanoethyl ester (1.12 g, 3.00 mmol) and 4-amino-3-penten-2-one (330 mg, 3.30 mmol) in 20 ml of EtOH was refluxed for 48 hrs. After the EtOH was removed in vacuo, the residue was dissolved in 150 ml of CHCl3, washed with water (2×100 ml) and dried over Na2SO4. After filtration and evaporation of solvent, the product was purified by chromatography (SiO2, CHCl3:MeOH=5:95). 5-Acetyl-2-(4-azidobutyl)-3-(2-cyanoethoxy)carbonyl-1,4-dihydro-6-methyl-4-(4-nitrophenyl)pyridine was obtain as a yellow oil (1.05 g, 77% yield). After the EtOH was removed in vacuo the residue was dissolved in 150 ml of CHCl3 washed with water (2×100 ml) dried over Na2SO4 After filtration and evaporation of solvent the product was purified by chromatography (SiO2, CHCl3:MeOH=5:95)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 7-azido-2-[(4-nitrophenyl)methylene]-3-oxoheptanoic acid 2-cyanoethyl ester (1.12 g, 3.00 mmol) and 4-amino-3-penten-2-one (330 mg, 3.30 mmol) in 20 ml of EtOH was refluxed for 48 hrs. After the EtOH was removed in vacuo, the residue was dissolved in 150 ml of CHCl3, washed with water (2×100 ml) and dried over Na2SO4. After filtration and evaporation of solvent, the product was purified by chromatography (SiO2, CHCl3:MeOH=5:95). 5-Acetyl-2-(4-azidobutyl)-3-(2-cyanoethoxy)carbonyl-1,4-dihydro-6-methyl-4-(4-nitrophenyl)pyridine was obtain as a yellow oil (1.05 g, 77% yield). After the EtOH was removed in vacuo the residue was dissolved in 150 ml of CHCl3 washed with water (2×100 ml) dried over Na2SO4 After filtration and evaporation of solvent the product was purified by chromatography (SiO2, CHCl3:MeOH=5:95)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 7-azido-2-[(4-nitrophenyl)methylene]-3-oxoheptanoic acid 2-cyanoethyl ester (1.12 g, 3.00 mmol) and 4-amino-3-penten-2-one (330 mg, 3.30 mmol) in 20 ml of EtOH was refluxed for 48 hrs. After the EtOH was removed in vacuo, the residue was dissolved in 150 ml of CHCl3, washed with water (2×100 ml) and dried over Na2SO4. After filtration and evaporation of solvent, the product was purified by chromatography (SiO2, CHCl3:MeOH=5:95). 5-Acetyl-2-(4-azidobutyl)-3-(2-cyanoethoxy) carbonyl-1,4-dihydro-6-methyl-4-(4-nitrophenyl) pyridine was obtain as a yellow oil (1.05 g, 77% yield). After the EtOH was removed in vacuo the residue was dissolved in 150 ml of CHCl3 washed with water (2×100 ml) dried over Na2SO4 After filtration and evaporation of solvent the product was purified by chromatography (SiO2, CHCl3:MeOH=5:95)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 7-azido-2-[(4-nitrophenyl)methylene]-3-oxoheptanoic acid 2-cyanoethyl ester (1.12 g, 3.00 mmol) and 4-amino-3-penten-2-one (330 mg, 3.30 mmol) in 20 ml of EtOH was refluxed for 48 hrs. After the EtOH was removed in vacuo, the residue was dissolved in 150 ml of CHCl3, washed with water (2×100 ml) and dried over Na2SO4. After filtration and evaporation of solvent, the product was purified by chromatography (SiO2, CHCl3:MeOH=5:95). 5-Acetyl-2-(4-azidobutyl)-3-(2-cyanoethoxy) carbonyl-1,4-dihydro-6-methyl-4-(4-nitrophenyl) pyridine was obtain as a yellow oil (1.05 g, 77% yield). After the EtOH was removed in vacuo the residue was dissolved in 150 ml of CHCl3 washed with water (2×100 ml) dried over Na2SO4 After filtration and evaporation of solvent the product was purified by chromatography (SiO2, CHCl3:MeOH=5:95)