Über die Eigenschaften von Mannich‐Basen des Antipyrins mit aromatischen Aminen

Bodendorf, K.; H, Raaf

doi:10.1002/jlac.19555920104

Cited by 14 publications

(6 citation statements)

References 9 publications

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“…Similarly, the base peak in the mass spectrum of + the phenyl analog 8b was at m/e 1 18 (PhC_NMe + ct PhC=NMe). These results are in agreement with previous reports that the pyrazolone ring is preferentially methylated with dimethyl sulfate at N-2 (8,9).…”

Section: Nh2 III Mle 93supporting

confidence: 94%

Derivatives of 2-Pyrazolin-5-one. II. Catalyzed Sodium Borohydride Reduction of Some 4–(2-Nitrobenzylidene)-2-pyrazolin-5-ones. A Reappraisal

Coutts¹,

El-Hawari²

1975

Can. J. Chem.

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A reexamination of the sodium borohydride and palladium-charcoal reduction of 3-methyl-4-(o-nitrobenzylidene)-1-phenyl-2-pyrazolin-5-one (3a) has revealed that the final product is 3-methyl-4-(o-aminobenzyl)-1-phenyl-2-pyrazolin-5-one (Sa), and not 9-hydroxy-3-methyl3a,4,9,9a-tetrahydro-1 H-pyrazolo[3,4-blquinoline as claimed previously. Reduction of 3a to 5a proceeds via the 4-(0-nitrobenzyl) compound. Chemical and physical properties of 5a are described which support the assignment of this revised structure to the reduction product of 3a. Two analogs of 3a were also reduced in the same manner and yielded products analogous to 5a and not the previously claimed pyrazolo[3,4-blquinolines.RONALD T. COU'ITS et ABDEL-MONAEM EL-HAWARI. Can. J. Chem. 53,3637 (1975).Un reexamen de la reduction, par le borohydrure de sodium et le palladium sur charbon, de la methyl-3 (0-nitrobenzy1idene)-4 phtnyl-1 pyrazoline-2 one-5 (3a) revele que le produit final est la methyl-3 (0-aminobenzy1)-4 phenyl-1 pyrazoline-2 one-5 (5a) et non pas l'hydroxy-9 methyl-3 tetrahydro-3a,4,9,9a 1H-pyrazolo[3,4-b]quinoleine tel qu'il avait ete pretendu anterieurement. La reduction de 3a en 5a se produit par l'intermediaire du compose (o-nitrobenzy1)-4. Les proprittes chimiques et physiques de 5a sont en accord avec la structure revisie du produit de reduction de 3a. On a aussi reduit de la m&me maniere deux analogues de 3a; ils conduisent aussi a des produits analogues a 5a et non pas aux pyrazolo[3,4-b1quinolCines proposkes anterieurement.[Traduit par le journal] Narang et al.(1) first claimed that one product of the reduction of 3-methyl-4-(0-nitrobenzylidene)-1-phenyl-2-pyrazolin-5-one (la) by aluminum amalgam, zinc and acetic acid, or alcoholic hydrochloric acid, was a cyclic hydroxylamine, namely 9-hydroxy-3-methyl-3a,4,9,9a-tetrahydro-1 H-pyrazolo[3,4-blquinoline, 2a. The same product was the major one obtained by us (2) when l a was reduced with sodium borohvdride and palladium-charcoal or with cyclohexene and palladium-charcoal. We also concluded that other N-hydroxypyrazolo[3,4-blquinolines (2b-2e), together with unidentified reduced products, were formed when the appropriate pyrazolones (16-le) were similarly reduced. We now report that some of our previous conclusions (2) were erroneous. A more detailed investigation of the reduction of three pyrazolones (la-lc) is now described and the major products correctly identified. Structures of previously unidentified products have also been deduced. Chemical proper-'A previous study (2) is considered to be part I of the series.ties of the products of reduction of pyrazolones (la-lc) are also described.Initially the (0-nitrobenzylidene)pyrazolones (la-lc) were reduced by the previously reported method (2) except that methanol was used as solvent instead of an ethanol-methanol mixture. The same products were isolated, i.e. the major amphoteric compounds which were claimed to be the 9-hydroxypyrazolo[3,4-blquinolines (2a-2c), and the minor ones which had been left unidentified. However, due to som...

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Section: Nh2 III Mle 93supporting

confidence: 94%

Derivatives of 2-Pyrazolin-5-one. II. Catalyzed Sodium Borohydride Reduction of Some 4–(2-Nitrobenzylidene)-2-pyrazolin-5-ones. A Reappraisal

Coutts¹,

El-Hawari²

1975

Can. J. Chem.

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“…The use of recycled [bmim]PF 6 was investigated by the reaction of 1 with aniline. High yields were obtained until the fourth regeneration of [bmim]PF 6 . The results are shown in Figure 3.…”

Section: Resultsmentioning

confidence: 99%

“…In most cases, respective products were obtained in good to excellent yields (Table I). In order to check the general applicability of this protocol, we reacted N,N-dimethylaminomethylferrocene 4 with aryl amines in [bmim]PF 6 . Preliminary investigations carried out at room temperature did not yield quantitative results.…”

Section: Resultsmentioning

confidence: 99%

“…Until the mid-1970s, aryl amines were sporadically reported to react with various functionalities like phenols 4 and heterocyclic compounds. 5,6 More recently, arylaminomethylation of acetophenones has been studied extensively by the addition to a Schiff base generated in situ. [7][8][9] The amine exchange reaction, which consists of the interaction between an alkyl amine Mannich base and an aryl amine as reported by Singh and Singh, 10 also provides a route to aryl amine Mannich bases.…”

Section: Introductionmentioning

confidence: 99%

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Amine Exchange Reactions in Ionic Liquid

Rashinkar

Pore

Salunkhe

2009

Phosphorus, Sulfur, and Silicon and the Related Elements

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“…Altllough pyrazolone analgesics have now virtually vanished from the scene in North America and the Scandinavian countries (2), they are still widely used in other areas and considerable efforts have been expended to improve their pharmacological properties (3, 4). 111 recent years seine of this effort has been focused on 4-antipyrinaldehyle (Ib)%and its derivatives (5)(6)(7)(8)(9)(10)(11)(12)(13)(14), principally in connection wit11 antineuralgic and febrifugal effects. While insecticidal pyrazolones have been described (15)(16)(17), other nonanalgesic applications of 4-antipyrinaldehyde or its derivatives have received little attention other than brief reports of tuberculostatic (18) and bacteriostatic activity (10).…”

Section: Frederick J Ailan' and G Gr-11-iam Allan'mentioning

confidence: 99%

The Condensation of Rhodanine and Derivatives With 4-Antipyrinaldehyde

Allan¹,

Allan²

1961

Can. J. Chem.

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More than three-quarters of a century has elapsed since antipyrine (Ia) was introduced into medicine by Knorr as an antipyretic and analgesic (1). Altllough pyrazolone analgesics have now virtually vanished from the scene in North America and the Scandinavian countries (2), they are still widely used in other areas and considerable efforts have been expended to improve their pharmacological properties (3, 4). 111 recent years seine of this effort has been focused on 4-antipyrinaldehyle (Ib)%and its derivatives (5-14), principally in connection wit11 antineuralgic and febrifugal effects. While insecticidal pyrazolones have been described (15-17), other nonanalgesic applications of 4-antipyrinaldehyde or its derivatives have received little attention other than brief reports of tuberculostatic (18) and bacteriostatic activity (10).

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Über die Eigenschaften von Mannich‐Basen des Antipyrins mit aromatischen Aminen

Cited by 14 publications

References 9 publications

Derivatives of 2-Pyrazolin-5-one. II. Catalyzed Sodium Borohydride Reduction of Some 4–(2-Nitrobenzylidene)-2-pyrazolin-5-ones. A Reappraisal

Derivatives of 2-Pyrazolin-5-one. II. Catalyzed Sodium Borohydride Reduction of Some 4–(2-Nitrobenzylidene)-2-pyrazolin-5-ones. A Reappraisal

Amine Exchange Reactions in Ionic Liquid

The Condensation of Rhodanine and Derivatives With 4-Antipyrinaldehyde

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