Pyrrolinone, III. Anellierte stickstoffhaltige 5,5‐Ringsysteme aus 3‐Pyrrolin‐2‐onen

Abstract

Durch Hydrierung von 1 entstehendes Diaminopyrrolinon wird mit Orthoameisensaureester oder Formamid zu den 5,6-Dihydropyrrolo[3,4-dJimidazol-4(3H)-onen 10 bzw. 11 kondensiert. Bei der entsprechenden Umsetzung rnit Acetylaceton sowie der Kondensation des hydrierten Hydrazonopyrrolidinonoxims 16 mit Orthoameisensaureester tritt keine Cyclisierung ein. Die Synthesen der 5,6-Dihydropyrrolo[3,4-dJfurazan-4-one 19 und 20, der 5,6-Dihydropyrrolo[3,4-d]furazan-4on-3-oxide 21 -24 und deren Reaktionen sowie die Synthese der 3-Imino-4,5-dihydropyrrolo[3,4c]pyrazol-6(3H)-one 34 und 35 werden beschrieben. Pyrrolinones, I11 1). -Annelated Nitrogen-containing 5,5-Ring Systems from 3-Pyrrolin-2-ones The 5,6-dihydropyrrolo[3,4-d]imidazol-4(3H)-ones 10 and 11 are formed by hydrogenation of 1 and condensation of the resulting diaminopyrrolinone with orthoformate or formamide, respectively. No cyclization occurs in the corresponding reaction with acetylacetone and on condensation of the hydrogenated hydrazonopyrrolidinone oxime 16 with orthoformate. The syntheses of the 5,6-dihydropyrrolo[3,4-d]furazan-4-ones 19 and 20, of the 5,6-dihydropyrrolo[3,4-d]furazan-4one 3-oxides 21 -24, and their reactions, and the syntheses of the 3-imino-4,5-dihydropyrrolo[3,4-c]pyrazoI-6(3H)-ones 34 and 35 are described. Pyrrolinone mit stickstoffhaltigen in den b-Stellungen anellierten Fiinfringen sind noch nicht beschrieben. Auch uber derartige anellierte Pyrrolderivate ist nur wenig bekannt. Das erste Pyrazolopyrrolidinon stellten Dohrn und Thiele2), analoge Ringsysteme A e b i und Mitarbeiter31 sowie Jacquier und Mitarbeiter4) dar. Ein Hexahydropyrroloimidazol als vermutlichen Kofaktor fur Biotin-erfordernde Enzyme synthetisierten Wormer und Abrarnson5). * ) Korrespondenz bitte an diesen Autor richten.

Pyrrolidinetrione Derivatives: Synthesis And Applications in Heterocyclic Chemistry

“…During investigations of the novel Wittig-Smiles reaction of α-ketodicarboxylic acid chloride imide chloride 16 with alkylidene triphenyl phosphoranes leading to 2,5pyrrolidine derivatives, Capuano 20 obtained unexpectedly 4,4-dimethylpyrrolidine-2,3,5-trione derivatives 18 (Scheme 5), because the Wittig-Smiles reaction failed 21 when the ylide carbon carries either a methyl or phenyl substituent. Earlier, Capuano 22 described a method leading to pyrrolidinetriones 18 by direct cyclization of α-ketodicarboxylic acid chloride imide chloride 16 under influence of sodium hydroxide (Scheme 5).…”

“…On the other hand, an interesting result was obtained during the synthesis of Schiff bases of pyrrolidine-2,3,5-trione-type 36, involving anilides of 3-oxoacids. 21,27,43 For instance, while the reaction of the appropriate 3-oxoacid anilides with oxalyl A new route leading to dyestuffs 39, containing a pyrrolidine-2,3,5-trione moiety, was described by Katritzky. 44 The novel, colored indoxyl derivative 39 was prepared by reaction of 3,4-dichloro-N-phenylmaleinimide (38) and N-acyl indolin-3-one 37 (Scheme 12).…”

“…The hydrogenation of 3,4-dioximes of 1-alkyl/aryl-pyrrolidine-2,3,4-triones 108, catalyzed by PtO 2 , afforded a starting material for the synthesis of various anellated nitrogen-containing 5,5-ring systems. 21 Pyrrolo[3,4-d]imidazole derivatives 109 were formed by hydrogenation of 108 and condensation of the resulting diaminopyrrolidinewith orthoformate or formamide in high yields, respectively 21. 5,6-Dihydropyrrolo[3,4-c]furazan-4-one derivatives 110,21 which are very useful for polymer crosslinking,8 were obtained from dioximes 108 by treatment with thionyl chloride or acetic anhydride, respectively.…”