Some reactions with ω-bromoacetophenone: Synthesis of Δαβ-butenolide and its transformation into pyrrole derivativesDedicated to Prof. Shigeru Oae on the occasion of his seventy-fifth birthday.
ω-Bromoacetophenone reacts with the sodium salt of ethyl cyanoacetate to afford α-cyano-β-phenyl-Δαβ-butenolide. This butenolide undergoes azo coupling with diazotized aromatic amines (ArNH2) to afford the hydrazo derivatives. These hydrazo derivatives (Ar=Ph, 4-ClC6H4, 4-MeC6H4, 4-MeOC6H4) were transformed into the corresponding 3(2H)-pyridazinone derivatives on stirring in methanol in the presence of potassium hydroxide. These latter compounds were converted into the corresponding 3-cyano-2,5-dihydroxy-4-phenyl-N-arylpyrrole derivatives on reduction with zinc dust in refluxing acetic acid, presumably via reductive cleavage of the N—N bond of the pyridazine followed by recyclization via loss of ammonia..
| Medienart: |
E-Artikel |
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| Erscheinungsjahr: |
1995 |
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| Erschienen: |
1995 |
| Reproduktion: |
Wiley InterScience Backfile Collection 1832-2000 |
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| Enthalten in: |
Zur Gesamtaufnahme - volume:6 |
| Enthalten in: |
Heteroatom Chemistry - 6(1995) vom: Jan., Seite 77-80 |
| Sprache: |
Englisch |
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| Beteiligte Personen: |
Abdelrazek, Fathy M. [Sonstige Person] |
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| Links: |
dx.doi.org [Deutschlandweit zugänglich] |
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| Umfang: |
2 Tab. 4 |
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| Förderinstitution / Projekttitel: |
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| PPN (Katalog-ID): |
NLEJ162439938 |
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| 245 | 1 | 0 | |a Some reactions with ω-bromoacetophenone: Synthesis of Δαβ-butenolide and its transformation into pyrrole derivativesDedicated to Prof. Shigeru Oae on the occasion of his seventy-fifth birthday. |
| 264 | 1 | |c 1995 | |
| 300 | |b 2 Tab. | ||
| 300 | |a 4 | ||
| 336 | |a nicht spezifiziert |b zzz |2 rdacontent | ||
| 337 | |a nicht spezifiziert |b z |2 rdamedia | ||
| 338 | |a nicht spezifiziert |b zu |2 rdacarrier | ||
| 520 | |a ω-Bromoacetophenone reacts with the sodium salt of ethyl cyanoacetate to afford α-cyano-β-phenyl-Δαβ-butenolide. This butenolide undergoes azo coupling with diazotized aromatic amines (ArNH2) to afford the hydrazo derivatives. These hydrazo derivatives (Ar=Ph, 4-ClC6H4, 4-MeC6H4, 4-MeOC6H4) were transformed into the corresponding 3(2H)-pyridazinone derivatives on stirring in methanol in the presence of potassium hydroxide. These latter compounds were converted into the corresponding 3-cyano-2,5-dihydroxy-4-phenyl-N-arylpyrrole derivatives on reduction with zinc dust in refluxing acetic acid, presumably via reductive cleavage of the N—N bond of the pyridazine followed by recyclization via loss of ammonia. | ||
| 533 | |f Wiley InterScience Backfile Collection 1832-2000 | ||
| 700 | 1 | |a Abdelrazek, Fathy M. |4 oth | |
| 700 | 1 | |a Kandeel, Zaghloul E. |4 oth | |
| 700 | 1 | |a Salah, Abdellatif M. |4 oth | |
| 773 | 0 | 8 | |i in |t Heteroatom Chemistry |d New York, NY [u.a.] : Wiley |g 6(1995) vom: Jan., Seite 77-80 |w (DE-627)NLEJ159071143 |w (DE-600)1483690-7 |x 1042-7163 |7 nnns |
| 773 | 1 | 8 | |g volume:6 |g year:1995 |g month:01 |g pages:77-80 |g extent:4 |
| 856 | 4 | 0 | |u http://dx.doi.org/10.1002/hc.520060116 |q text/html |z Deutschlandweit zugänglich |
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