N-(α-Amidoalkyl)benzotriazole-mediated synthesis of β′-amido β-diketones: a general synthetic protocol for N-[β-(3,5-di and 1,3,5-trisubstituted pyrazol-4-yl)alkyl] amides

Çelik, İ̇lhami; Kaniskan, Nevin; Kökten, Şule

doi:10.1016/j.tet.2008.10.047

Cited by 8 publications

(4 citation statements)

References 49 publications

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“…Very recently, the reaction between N ‐(α‐amidoalkyl)‐benzotriazoles and 1,3‐diketones‐dervied potassium enolates was used for the preparation of the β‐amido β‐diketones by the loss of Bt [6]. Combination with Katritzky's research [5a] and ours, it could be concluded that Bt is a better leaving group than either amido or alkoxycarbonylamino because the enolates consistently substitute the Bt in the three types of substrates.…”

Section: Resultsmentioning

confidence: 70%

Selective substitution reactions of methoxycarbonylamino‐1‐(1‐benzotriazolyl)alkanes with active methylene compounds

Zhou

Mao

et al. 2011

Journal of Heterocyclic Chem

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Benzotriazole adducts methoxycarbonylamino‐1‐(1‐benzotriazolyl)alkanes 1 were derived from the condensation of an aldehyde, benzotriazole, and methylcarbamate. The leaving tendency of methoxycarbonylamino group (MeOCONH) and benzotriazole group (Bt) was investigated by treatment of the adducts with active methylene compounds under either Lewis acid‐catalyzed or basic conditions. In the presence of SmI3, MeOCONH take priority over Bt in the leaving process, whereas in the presence of MeONa, the Bt was substituted in preference. Thus, the tunable substitution of the two leaving groups could be used for different synthetic purposes. J. Heterocyclic Chem., 00, 00 (2011).

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Section: Resultsmentioning

confidence: 70%

Selective substitution reactions of methoxycarbonylamino‐1‐(1‐benzotriazolyl)alkanes with active methylene compounds

Zhou

Mao

et al. 2011

Journal of Heterocyclic Chem

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“…According to the pronounced biological activity [43] of pyrazole derivatives, the author intended to construct a new thienopyridine containing pyrazole ring via the reaction of the hydrazide derivative 13 [1] with acetyl acetone in an ethanolic solutions which afforded a mixture of the unexpected enaminoester 1 and 3,5-dimethylpyrazole derivative 14 in the ratio of 2:1, respectively. The latter products were separated by fractional crystallization (Scheme 3).…”

Section: Methodsmentioning

confidence: 99%

Synthetic utility of enaminoester moiety in heterocyclic synthesis

et al. 2010

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“…The pyrazole moiety also used in the fluorescence, luminescence, herbicides [21], ligands [22], in the preparation of dyes [23] and as the corrosion inhibitors [8,24]. The successfully commercialized drugs contains pyrazole moiety are celexib, fipronil, sildenafil [7], pyrazofurin, lonazolac, rimonabant, ramifenazone and phenylbutazone [9].…”

Section: Introductionmentioning

confidence: 99%

Molecular Docking Study of Novel Synthesized Pyrazole Derivatives and their Antibacterial Activity

Khumar¹,

Ezhilarasi²,

Prabha³

2018

Asian J. Chem.

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The current novel series of 1-[5-(furan-2-yl)-4,5-dihydro-3-(4-morpholinophenyl)pyrazol-1-yl]ethanone are synthesized from the 3-(furan-2-yl)-1-(4-morpholinophenyl)prop-2-ene-1-one by cyclization reaction. The 3-(furan-2-yl)-1-(4-morpholinophenyl)prop-2-ene-1-one chalcones are derived from the reaction of 4-morpholino acetophenone with substituted furfuraldehyde by common Claisen-Schmidt condensation reaction. The structures of the synthesized compounds skeleton are elucidated by IR, 1 H NMR and 13 C NMR. The antimicrobial susceptibility tests of synthesized compounds are screened against Staphylococcus aureus and Escherichia coli. From the three synthesized compounds the electron-withdrawing substitution (Br) shows good effect against the Gram-positive bacteria and the electron donating substitution (CH3) shows excellent inhibition zone against the Gram-negative bacteria at the concentration level (10 µg/mL). The molecular docking is an effective and component tool for in silico screening of bioactive compounds and Auto Dock 4.2.1 is used to find the binding interaction of synthesized compounds towards 3 selected bacterial proteins (2X5O, 3TYE, 3UDI).

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N-(α-Amidoalkyl)benzotriazole-mediated synthesis of β′-amido β-diketones: a general synthetic protocol for N-[β-(3,5-di and 1,3,5-trisubstituted pyrazol-4-yl)alkyl] amides

Cited by 8 publications

References 49 publications

Selective substitution reactions of methoxycarbonylamino‐1‐(1‐benzotriazolyl)alkanes with active methylene compounds

Selective substitution reactions of methoxycarbonylamino‐1‐(1‐benzotriazolyl)alkanes with active methylene compounds

Synthetic utility of enaminoester moiety in heterocyclic synthesis

Molecular Docking Study of Novel Synthesized Pyrazole Derivatives and their Antibacterial Activity

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