Summary
Approaches leading to 5,6-dihydro-5,6-diphenyl-2-substituted-pyrrolo[3,4-d][1,2,3]-triazol-4(2H,4H)-ones (10) are described. The first approach consists of cyclodehydrating 3(or 4)-hydroxyimino-1,5-diphenyl-4(or 3)-(4-substituted phenylhydrazono)pyrrolidin-2-ones (4,7) with boiling acetic anhydride. The second approach involves cyclization of 3(or 4)-acetoxyimino-1,5-diphenyl-4(or 3)-(4-substituted phenylhydrazono)pyrrolidin-2-ones (8,9) with elimination of acetic acid upon treatment with sodium hydroxide.
Zusammenfassung
Es werden zwei neue Wege zur Synthese von 5,6-dihydro-5,6-diphenyl-2-substituierten Pyrrolo[3,4-d][1,2,3]triazol-4(2H,4H)-onen (10) beschrieben. Der erste Weg besteht aus der Cyclodehydrierung von 3(oder 4)-Hydroxyimino-1,5-diphenyl-4(oder 3)-(4-subst.phenylhydrazono)pyrrolidin-2-onen (4,7) mit kochendem Essigsäureanhydrid. Der zweite Weg benutzt eine Cyclisierung von 3(oder 4)-Acetoxyimino-1,5-diphenyl-4(oder 3)-(4-subst.phenylhydrazono)-pyrrolidin-2-onen (8,9) unter Eliminierung von Essigsäure nach Behandlung mit Natriumhydroxyd.
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Kassem, M.G., Shams El-Dine, S.A., Soliman, F.S.G. et al. Reactions with pyrrolidine-2,4-diones, II: New approaches to the synthesis of substituted 5,6-dihydropyrrolo[3,4-d][1,2,3]triazol-4(2H,4H)ones. Monatsh Chem 121, 671–675 (1990). https://doi.org/10.1007/BF00809771
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DOI: https://doi.org/10.1007/BF00809771