3-Oxo-3-phenylpropyne → 2-Benzoylpyrazolo[1,5-c]quinazolin-5(6H)-one

HRID 1763499

Reaktionsgleichung

Reaktionsgleichung von HRID 1763499
[N+:1](=[C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[NH:5][C:4]1=[O:12])=[N-:2].[C:13]1([C:19]([C:21]#[CH:22])=[O:20])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>>[C:19]([C:21]1[CH:22]=[C:3]2[N:1]([C:4](=[O:12])[NH:5][C:6]3[CH:7]=[CH:8][CH:9]=[CH:10][C:11]=32)[N:2]=1)(=[O:20])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Komponenten

3

Edukt 2

HCID 771793-Oxo-3-phenylpropyneHCID 136455454(3Z)-3-diazo-1H-indol-2-one

Produkt 1

HCID 1357375902-Benzoylpyrazolo[1,5-c]quinazolin-5(6H)-one

Versuchsvorschrift

6.23 g (0.039 mole) of diazooxindole and 6.6 g (0.051 mole or 1.3 equiv) of the phenylethynyl ketone prepared as in part A above (dried on a porous plate before being weighed out) are suspended in benzene (275 ml) and the mixture is refluxed under N2 for 19 hours. The reaction mixture is cooled and the precipitates that form are filtered off, washed well with anhydrous ether (150 ml) and dried in a vacuum oven at ~70° for 11/2 hours. Yield: 10.3 g, m.p. 308°-311°. Additional product of 400 mg is obtained on refluxing the filtrate for another 24 hours. Total crude yield: 94.4%.

Aufarbeitung

  1. customdried on a porous plate
  2. temperaturethe mixture is refluxed under N2 for 19 hours
  3. temperatureThe reaction mixture is cooled
  4. customthe precipitates that form
  5. filtrationare filtered off
  6. washwashed well with anhydrous ether (150 ml)
  7. customdried in a vacuum oven at ~70° for 11/2 hours
  8. customAdditional product of 400 mg is obtained
  9. temperatureon refluxing the filtrate for another 24 hours

Quellen und Nachweise

ORD-Eintrag
ord-d43ca0310e314bba9b094540980486e9
Quelldatensatz
uspto-grants-1978_09
Patentnummer
US04112096

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