Synthesis of new pyrazole and isoxazole derivatives based on products of condensation of ?-dicarbonyl compounds with 1,2,3-trihalopropanes

Akhmedov, Sh. T.; Sadykhov, N. S.; Ismailov, V. M.; Akhundova, M. A.; Mamedov, M. M.; Kozhushkov, Sergei I.; Зефиров, Н. С.

doi:10.1007/bf00486912

Cited by 2 publications

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“…We failed to obtain the 1 H NMR spectrum of pyrazole IIc in CDCl 3 due to its poor solubility. Our results are consistent with published data [7]. …”

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confidence: 96%

Synthesis and Some Chemical Transformations of Adamantyl-Substituted Pyrazolones

2010

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1-Substituted 3-(1-adamantyl)-4,5-dihydro-1H-pyrazol-5-ones and 3-(1-adamantyl)-4,5-dihydroisoxazol-5-one were synthesized by reaction of ethyl 3-(1-adamantyl)-3-oxopropanoate with various hydrazine derivatives and hydroxylamine hydrochloride. Nitrosation of adamantyl-substituted pyrazolones with sodium nitrite in acetic acid gave the corresponding 4-hydroxyimino derivatives. Reactions of 3-(1-adamantyl)-4,5-dihydro-1H-pyrazol-5-ones and 3-(1-adamantyl)-4,5-dihydroisoxazol-5-one with aromatic and heterocyclic aldehydes led to the formation of condensation products at position 4 of the heteroring. R = H (a), Ph (b), CONH 2 (c), 4-O 2 NC 6 H 4 (d).1,2-Diazole derivatives are used as pyrazolone dyes, materials for optoelectronics, pesticides, and medical agents, and they attract interest due to diversity of their chemical transformations. Many drugs (e.g., aminophenazone, metamizole sodium, celecoxib, phenazone) are heterocyclic derivatives of 1,3-dicarbonyl compounds [1].3-(1-Adamantyl)-and 3-(1-adamantylmethyl)-1-phenyl-4,5-dihydro-1H-pyrazol-5-ones were synthesized for the first time from keto esters [2, 3], and their chemical behavior was not studied. Reactions of adamantyl-containing dioxocarboxylic acid esters with hydrazine and phenylhydrazine were reported [4]; depending on the initial ester, the reaction involved either elimination of acetyl group with formation of 3-(1-adamantylmethyl)-4,5-dihydro-1H-pyrazol-5-one or 3-(1-adamantylmethyl)-1-phenyl-4,5-dihydro-1H-pyrazol-3-one [from ethyl 4-(1-adamantyl)-2-acetyl-3-oxobutanoate] or decomposition of the initial dioxo ester with formation of adamantane-1-carbohydrazide [from ethyl 2-(1-adamantylcarbonyl)-3-oxobutanoate.Due to the presence of an activated methylene group in position 4, 3-methyl-1-phenyl-4,5-dihydro-1H-pyrazol-5-one undergoes halogenation, nitrosation, nitration, and condensation with benzaldehyde and acetone [5]. There are no published data on the chemical behavior of adamantyl-substituted pyrazolones. In the present article we report the results of our study on the synthesis of adamantyl-substituted pyrazolones and their chemical transformations. Pyrazolones IIa-IId

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“…We failed to obtain the 1 H NMR spectrum of pyrazole IIc in CDCl 3 due to its poor solubility. Our results are consistent with published data [7]. …”

supporting

confidence: 96%

Synthesis and Some Chemical Transformations of Adamantyl-Substituted Pyrazolones

2010

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“…The alkylation reactions of β-dicarbonyl derivatives with dibromide and 1,2,3-trihalopropane derivatives have been studied in detail [1][2][3] and the products obtained have been used in the synthesis of various heterocyclic compounds. Although many researchers have been working on synthesis of novel spiro derivatives [4][5][6][7][8][9][10][11][12][13][14][15][16][17][18][19][20][21][22], we did not come across any studies of the alkylation of β-dicarbonyl derivatives with 2-chloro-1-(2-chloroethoxy)ethane in the literature.…”

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confidence: 99%

Quantum Chemical and Experimental Studies on the Mechanism of Alkylation of β-Dicarbonyl Compounds. The Synthesis of Five and Six Membered Heterocyclic Spiro Derivatives

Sadikov¹,

Nasibov²,

Öğretır

et al. 2004

Molecules

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Abstract:The alkylation of β-dicarbonyl compounds in a K 2 CO 3 /DMSO system was found to afford O-and C-alkylated derivatives, depending on the type of the β-dicarbonyl compound involved. The alkyl derivatives obtained were used in the synthesis of some new spiro barbituric acid derivatives. Quantum chemical calculations were carried out to elucidate the reaction mechanisms for some typical synthesis.

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Synthesis of new pyrazole and isoxazole derivatives based on products of condensation of ?-dicarbonyl compounds with 1,2,3-trihalopropanes

Cited by 2 publications

References 4 publications

Synthesis and Some Chemical Transformations of Adamantyl-Substituted Pyrazolones

Synthesis and Some Chemical Transformations of Adamantyl-Substituted Pyrazolones

Quantum Chemical and Experimental Studies on the Mechanism of Alkylation of β-Dicarbonyl Compounds. The Synthesis of Five and Six Membered Heterocyclic Spiro Derivatives

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