Conditions | Yield |
---|---|
With hydrazine In tetrahydrofuran; ethanol at 0 - 60℃; for 26h; Inert atmosphere; | 100% |
With hydrazine hydrate at 20℃; for 0.0333333h; Knorr Pyrazole Synthesis; | 100% |
With hydrazine for 0.00833333h; | 94% |
Conditions | Yield |
---|---|
With barium(II) hydroxide In water at 26℃; for 0.75h; Green chemistry; | 100% |
Conditions | Yield |
---|---|
With hydrazine hydrate In methanol at 50℃; for 3h; Temperature; Inert atmosphere; | 97.3% |
With hydrazine In ethanol |
N-acetoacetylphenylhydroxyloamine
A
N,N'-bis(isonicotinoyl)hydrazine
B
N-Phenylhydroxylamine
C
3-methyl-2-pyrazoline-5-one
D
azoxybenzene
Conditions | Yield |
---|---|
With isoniazid; triethylamine In chloroform for 24h; Heating; Further byproducts given; | A 39.5% B 32.7% C 90% D 22% |
N-acetoacetylphenylhydroxyloamine
isoniazid
A
N,N'-bis(isonicotinoyl)hydrazine
B
N-Phenylhydroxylamine
C
N-hydroxy-N-phenylisonicotinamide
D
3-methyl-2-pyrazoline-5-one
Conditions | Yield |
---|---|
triethylamine In chloroform for 24h; Heating; Further byproducts given; | A 39.5% B 32.7% C 23% D 90% |
isoniazid
A
N,N'-bis(isonicotinoyl)hydrazine
B
N-Phenylhydroxylamine
C
N-hydroxy-N-phenylisonicotinamide
D
3-methyl-2-pyrazoline-5-one
Conditions | Yield |
---|---|
With N,O-diacetylphenylhydroxylamine; triethylamine In chloroform for 24h; Heating; Further byproducts given; | A 39.5% B 32.7% C 23% D 90% |
Conditions | Yield |
---|---|
In ethanol Condensation; Cyclization; | 87% |
ethyl 2-acetyl-4,4,5,5,6,6,7,7,7-nonafluoro-3-oxoheptanoate
phenylhydrazine
A
2,2,3,3,4,4,5,5,5-Nonafluoro-pentanoic acid N'-phenyl-hydrazide
B
3-methyl-2-pyrazoline-5-one
Conditions | Yield |
---|---|
In diethyl ether at -30 - -25℃; for 1h; | A 84% B n/a |
2-Acetyl-4,4,5,5,6,6,7,7,8,8,9,9,9-tridecafluoro-3-oxo-nonanoic acid ethyl ester
phenylhydrazine
A
2,2,3,3,4,4,5,5,6,6,7,7,7-Tridecafluoro-heptanoic acid N'-phenyl-hydrazide
B
3-methyl-2-pyrazoline-5-one
Conditions | Yield |
---|---|
In diethyl ether at -30 - -25℃; for 1h; | A 79% B n/a |
ethyl acetoacetate
N-d-pseudoephedrinylacetic acid hydrazide
A
3-methyl-2-pyrazoline-5-one
B
(5S,6S)-4,5-dimethyl-6-phenyl-2-morpholone
Conditions | Yield |
---|---|
In isopropyl alcohol for 10h; Condensation; cyclization; elimination; Heating; | A n/a B 68% |
phenylhydrazine
ethyl 2-acetylacetoacetate
A
3-methyl-2-pyrazoline-5-one
B
1-acetyl-2-phenylhydrazine
Conditions | Yield |
---|---|
In diethyl ether at -30 - -25℃; | A n/a B 64% |
ethyl acetoacetate
N-l-ephedrinylacetic acid hydrazide
A
(5S,6R)-4,5-dimethyl-6-phenylmorpholin-2-one
B
3-methyl-2-pyrazoline-5-one
Conditions | Yield |
---|---|
In isopropyl alcohol for 10h; Condensation; cyclization; elimination; Heating; | A 62% B n/a |
3-methyl-2-pyrazoline-5-one
Conditions | Yield |
---|---|
With hydrazine In dichloromethane at 20℃; for 19h; | 50% |
2-Acetyl-4,4,5,5,6,6,7,7,8,8,9,9,9-tridecafluoro-3-oxo-nonanoic acid ethyl ester
phenylhydrazine
A
2,2,3,3,4,4,5,5,6,6,7,7,7-Tridecafluoro-heptanoic acid N'-phenyl-hydrazide
B
5-Methyl-1-phenyl-3-tridecafluorohexyl-1H-pyrazole-4-carboxylic acid ethyl ester
C
3-methyl-2-pyrazoline-5-one
Conditions | Yield |
---|---|
In ethanol at -30 - -25℃; for 1h; | A n/a B 27% C n/a |
ethyl 2-(1-adamantylcarbonyl)-3-oxobutanoate
A
3-(1-adamantyl)-4,5-dihydro-1H-pyrazol-5-one
B
adamantane-1-carbohydrazide
C
3-methyl-2-pyrazoline-5-one
Conditions | Yield |
---|---|
With hydrazine hydrate In ethanol Cooling; | A 25% B 24% C 11% |
ethyl 2-acetyl-4,4,5,5,6,6,7,7,7-nonafluoro-3-oxoheptanoate
phenylhydrazine
A
2,2,3,3,4,4,5,5,5-Nonafluoro-pentanoic acid N'-phenyl-hydrazide
B
5-Methyl-3-nonafluorobutyl-1-phenyl-1H-pyrazole-4-carboxylic acid ethyl ester
C
3-methyl-2-pyrazoline-5-one
Conditions | Yield |
---|---|
In ethanol at -30 - -25℃; for 1h; | A n/a B 14% C n/a |
3-methyl-5-oxo-3-pyrazolin-1-carboxamide
3-methyl-2-pyrazoline-5-one
Conditions | Yield |
---|---|
geht allmaehlich in 3-Methyl-pyrazolon-(5) ueber; |
Conditions | Yield |
---|---|
at 120℃; |
S-ethyl acetothioacetate
A
1,2-dihydro-5-methyl-3H-pyrazol-3-one
B
5-Hydroxy-5-methyl-pyrazolidin-3-one
C
3-methyl-2-pyrazoline-5-one
D
ethanethiol
Conditions | Yield |
---|---|
With hydrazine In methanol; water at 30℃; not separated; | |
With hydrazine In methanol; water at 30℃; Rate constant; Kinetics; Mechanism; |
ethyl acetoacetate (Z)-semicarbazone
A
hydrazodicarboxamide
B
3-methyl-2-pyrazoline-5-one
Conditions | Yield |
---|---|
In water for 1h; Heating; | A 0.30 g B 0.12 g |
sulfuric acid
3-ethoxy-5-methyl-1H-pyrazole
3-methyl-2-pyrazoline-5-one
Conditions | Yield |
---|---|
at 140 - 150℃; |
3-methyl-5-oxo-3-pyrazolin-1-carboxamide
water
3-methyl-2-pyrazoline-5-one
2-[amino(thioxo)methyl]-5-methyl-2,3-dihydro-1H-3-pyrazolone
water
3-methyl-2-pyrazoline-5-one
water
ethyl acetoacetate
hydrazine hydrate
3-methyl-2-pyrazoline-5-one
2-[amino(thioxo)methyl]-5-methyl-2,3-dihydro-1H-3-pyrazolone
3-methyl-2-pyrazoline-5-one
2-[amino(thioxo)methyl]-5-methyl-2,3-dihydro-1H-3-pyrazolone
3-methyl-2-pyrazoline-5-one
Conditions | Yield |
---|---|
at 120℃; im Druckrohr; |
piperidine
ethyl acetoacetate
2-phenylacetylhydrazine
A
1,2-di(phenylacetyl)hydrazine
B
3-methyl-2-pyrazoline-5-one
Conditions | Yield |
---|---|
at 20℃; |
water
A
ammonia
B
ethyl acetoacetate
C
methylammonium carbonate
D
3-methyl-2-pyrazoline-5-one
3-methyl-2-pyrazoline-5-one
Conditions | Yield |
---|---|
Stage #1: 2-(4,6-dimethyl-3-cyano-2-pyridinylthio)benzenediazonium nitrate; 3-methyl-2-pyrazoline-5-one for 0.0833333h; grinding; Stage #2: With trimethylamine at 20℃; under 375.038 Torr; for 12h; Further stages.; | 100% |
Conditions | Yield |
---|---|
Stage #1: α-bromoacetophenone; 3-methyl-2-pyrazoline-5-one at 20℃; for 1h; ball-milling; Stage #2: With sodium carbonate Further stages.; | 100% |
Conditions | Yield |
---|---|
In water at 60℃; for 0.25h; Green chemistry; | 100% |
With ethanol; sodium acetate at 20℃; for 0.5h; Green chemistry; | 83% |
m-bromobenzoic aldehyde
3-methyl-2-pyrazoline-5-one
malononitrile
[(3-bromophenyl)(5-hydroxy-3-methyl-1H-pyrazol-4-yl)methyl]malononitrile
Conditions | Yield |
---|---|
With ethanol; sodium acetate at 20℃; for 1h; Green chemistry; | 99% |
Conditions | Yield |
---|---|
With water at 20℃; for 0.166667h; Solvent; Green chemistry; | 99% |
Conditions | Yield |
---|---|
With water at 20℃; for 0.166667h; Green chemistry; | 99% |
5-chloroindole 2,3-dione
3-methyl-2-pyrazoline-5-one
Conditions | Yield |
---|---|
With water at 20℃; for 0.166667h; Green chemistry; | 99% |
5-iodoisatin
3-methyl-2-pyrazoline-5-one
Conditions | Yield |
---|---|
With water at 20℃; for 0.166667h; Green chemistry; | 99% |
Conditions | Yield |
---|---|
With water at 20℃; Green chemistry; | 99% |
5-methoxyisatine
3-methyl-2-pyrazoline-5-one
Conditions | Yield |
---|---|
With water at 20℃; for 0.166667h; Green chemistry; | 99% |
3-methyl-2-pyrazoline-5-one
5-trifluoromethoxy-1H-indole-2,3-dione
Conditions | Yield |
---|---|
With water at 20℃; for 0.166667h; Green chemistry; | 99% |
Conditions | Yield |
---|---|
With water at 20℃; for 0.166667h; Green chemistry; | 99% |
Conditions | Yield |
---|---|
With water at 20℃; for 0.166667h; Green chemistry; | 99% |
4-chlorobenzaldehyde
3-methyl-2-pyrazoline-5-one
malononitrile
6‐amino‐3‐methyl‐ 4‐(4‐chlorophenyl)‐1,4‐dihydropyrano[2,3‐c]pyrazole‐5‐carbonitrile
Conditions | Yield |
---|---|
With MgFeCrO4 In ethanol; water for 0.0833333h; Catalytic behavior; Solvent; Time; Reflux; | 98% |
With H3PO4/Al2O3 In neat (no solvent) at 100℃; for 0.1h; Reagent/catalyst; Green chemistry; | 97% |
With C8H19N2(1+)*HO(1-) In ethanol; water for 0.0833333h; Solvent; Microwave irradiation; | 95% |
benzaldehyde
3-methyl-2-pyrazoline-5-one
malononitrile
6-amino-1,4-dihydro-3-methyl-4-phenylpyrano[2,3-c]pyrazole-5-carbonitrile
Conditions | Yield |
---|---|
With sodium hydroxide In water at 100℃; for 1h; Reagent/catalyst; Temperature; Time; Solvent; Green chemistry; | 98% |
Stage #1: benzaldehyde; malononitrile In ethanol; water at 20℃; for 0.25h; UV-irradiation; Green chemistry; Stage #2: 3-methyl-2-pyrazoline-5-one In ethanol; water at 20℃; for 0.75h; UV-irradiation; Green chemistry; | 98% |
With H3PO4/Al2O3 In neat (no solvent) at 100℃; for 0.116667h; Catalytic behavior; Reagent/catalyst; Temperature; Green chemistry; | 97% |
1-amino-9,10-dioxo-9,10-dihydro-anthracene-2-carbaldehyde
3-methyl-2-pyrazoline-5-one
1-amino-2-<(3-methyl-5-oxo-2-pyrazolin-4-ylidene)methyl>anthraquinone
Conditions | Yield |
---|---|
With potassium hydroxide In ethanol for 2h; Heating; | 98% |
Conditions | Yield |
---|---|
With phosphotungstic acid In ethanol for 0.25h; Reagent/catalyst; Temperature; Solvent; Time; Reflux; Green chemistry; | 98% |
With Santa Barbara Amorphous modified with propylsulfonic acid groups In neat (no solvent) at 120℃; for 0.0666667h; Catalytic behavior; Solvent; Green chemistry; | 95% |
With sodium dodecyl-sulfate In water for 1h; Heating; | 83.7% |
In glycerol at 80℃; for 0.05h; Green chemistry; |
5-chloroindole 2,3-dione
3-methyl-2-pyrazoline-5-one
malononitrile
6'‑amino‑3'‑methyl‑2‑oxo‑1'H‑spiro[5‑chloro‑indoline‑3,4'‑pyrano[2,3‑c]pyrazole]‑5'‑carbonitrile
Conditions | Yield |
---|---|
With bovine serum albumin In ethanol; water at 20℃; for 0.25h; Enzymatic reaction; | 98% |
With N-Sulfonic acid modified poly(styrene-co-maleic anhydride) In ethanol for 0.416667h; Reflux; Green chemistry; regioselective reaction; | 97% |
With potassium carbonate In water at 20℃; for 0.166667h; | 87.3% |
4,7-dichloroisatin
3-methyl-2-pyrazoline-5-one
Conditions | Yield |
---|---|
With water at 20℃; for 0.166667h; Green chemistry; | 98% |
Conditions | Yield |
---|---|
With 1,4-diazabicyclo[2.2.2]octane hydroacetate In water at 80℃; for 0.0833333h; Green chemistry; | 98% |
With phosphotungstic acid In ethanol for 1h; Reflux; Green chemistry; | 96% |
With Santa Barbara Amorphous modified with propylsulfonic acid groups In neat (no solvent) at 120℃; Green chemistry; | 87% |
In glycerol at 80℃; for 0.0333333h; Green chemistry; |
1,1,3-tricyano-2-amino-1-propene
salicylaldehyde
3-methyl-2-pyrazoline-5-one
Conditions | Yield |
---|---|
With triethylamine In propan-1-ol at 98℃; for 1h; Solvent; Reagent/catalyst; | 98% |
With triethylamine In propan-1-ol at 98℃; for 1h; Catalytic behavior; Reagent/catalyst; Solvent; | 98% |
4-nitrobenzaldehdye
3-methyl-2-pyrazoline-5-one
malononitrile
6‐amino‐3‐methyl‐4‐(4‐nitrophenyl)‐1,4‐dihydropyrano[2,3‐c]pyrazole‐5‐carbonitrile
Conditions | Yield |
---|---|
With H3PO4/Al2O3 In neat (no solvent) at 100℃; for 0.0833333h; Reagent/catalyst; Green chemistry; | 97% |
With piperidine In ethanol at 20℃; for 0.166667h; Green chemistry; | 90% |
In ethanol; water for 0.333333h; Reflux; Green chemistry; | 88% |
4-nitrobenzaldehdye
3-methyl-2-pyrazoline-5-one
malononitrile
6-amino-2,4-dihydro-4-(4-nitrophenyl)-3-methylpyrano[2,3-c]pyrazole-5-carbonitrile
Conditions | Yield |
---|---|
With propylamine functionalized nanoporous silica In ethanol at 20℃; for 0.25h; Green chemistry; | 97% |
With 2-carboxy-N,N-diethylethanaminium acetate In neat (no solvent) at 60℃; for 0.1h; | 93% |
With 1-methyl-3-methylimidazol-3-ium dimethyl phosphate In ethanol; water for 1h; Reflux; | 93% |
Conditions | Yield |
---|---|
With ethanol; sodium acetate at 20℃; for 1h; Time; Green chemistry; | 97% |
2,4-dichlorobenzaldeyhde
3-methyl-2-pyrazoline-5-one
malononitrile
6-amino-3-methyl-4-(2,4-dichlorophenyl)-1,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile
Conditions | Yield |
---|---|
With H3PO4/Al2O3 In neat (no solvent) at 100℃; for 0.0833333h; Reagent/catalyst; Green chemistry; | 97% |
Stage #1: 2,4-dichlorobenzaldeyhde; malononitrile With triethylamine In ethanol at 80℃; for 0.0333333h; Stage #2: 3-methyl-2-pyrazoline-5-one In ethanol at 80℃; for 0.25h; | 8% |
With C8H19N2(1+)*HO(1-) In water for 0.0833333h; Microwave irradiation; | |
In water at 20℃; for 2.5h; Green chemistry; | |
With aspirin In neat (no solvent) at 80℃; for 0.666667h; Green chemistry; |
11H-Indeno[1,2-b]quinoxaline-11-one
3-methyl-2-pyrazoline-5-one
malononitrile
3'-amino-7'-methyl-2-oxo-2H,5H'-spiro[(11H)-indeno(1',2'-b)quinoxalin-11,1'-pyrano[2,3-c]pyrazole]-2'-carbonite
Conditions | Yield |
---|---|
With triethylamine In ethanol for 1h; Mechanism; Reflux; | 97% |
Conditions | Yield |
---|---|
With phosphotungstic acid In ethanol for 1h; Reflux; Green chemistry; | 97% |
1. | unr-rat LDLo:600 mg/kg | BCPCA6 Biochemical Pharmacology. 14 (1965),1325. |
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