Synthesis and hypoglycemic evaluation of substituted pyrazole-4-carboxylic acids

Cottineau, Bertrand; Toto, Patrick; Marot, Christophe; Pipaud, Aline; Chenault, Jacques

doi:10.1016/s0960-894x(02)00380-3

Cited by 193 publications

(101 citation statements)

References 14 publications

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“…We have used trans-3,5-dihydroperoxy-3,5-dimethyl-1,2-dioxalane for in-situ generation of Cl ? as an effective electrophile from NH 4 Cl. Initially, the amounts of oxidant, NH 4 Cl, and solvent were optimized for oxidation of 1,3,5-triphenyl-1H-pyrazole (entry 1, Table 1).…”

Section: Resultsmentioning

confidence: 99%

“…Step 3: Scheme 3 Suggested mechanism for oxidative aromatization of 2-pyrazolines and isoxazolines listed in Table 1, water-MeCN was selected as solvent and the amounts of oxidant and NH 4 Cl were optimized (entry 10, Table 1). It is notable that addition of a catalytic amount of glacial acetic acid improved the yields and the reaction time.…”

Section: Resultsmentioning

confidence: 99%

“…Isoxazolines and pyrazolines are interesting five-membered heterocyclic compounds because of their biological and pharmacological importance, for example as anticancer [1], anti-viral [2], anti-inflammatory [3], anti-diabetic [4], anti-bacterial [5], antimicrobial, and antifungal agents [6]. Several isoxazoles and pyrazoles have agrochemical herbicidal and soil fungicidal activity and act as pesticides and insecticides [7,8].…”

Section: Introductionmentioning

confidence: 99%

“…So, in continuation of our interest in the application of trans-3,5-dihydroperoxy-3,5-dimethyl-1,2-dioxalane, we report the use of trans-3,5-dihydroperoxy-3,5-dimethyl-1,2-dioxalane-NH 4 ClHOAc for in situ generation of Cl ? from NH 4 Cl for catalysis of oxidative aromatization of 2-pyrazolines and isoxazolines (Scheme 1).…”

Section: Introductionmentioning

confidence: 99%

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Mild and efficient oxidation of 2-pyrazolines and isoxazolines by trans-3,5-dihydroperoxy-3,5-dimethyl-1,2-dioxalane–NH4Cl–HOAc in water–MeCN

Khosravi

2014

Res Chem Intermed

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show abstract

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Mild and efficient oxidation of 2-pyrazolines and isoxazolines by trans-3,5-dihydroperoxy-3,5-dimethyl-1,2-dioxalane–NH4Cl–HOAc in water–MeCN

Khosravi

2014

Res Chem Intermed

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“…They possess anti-obesity [4], antianxiety [5] and HIV-1 reverse transcriptase inhibitor [6], anti-hyperglycemic, anti-pyretic, analgesic, anti-inflammatory and hypoglycemic activity [7,8]. Their derivatives are used as important intermediates in the preparation of drug molecules, as well as in the laboratory synthesis of natural products.…”

Section: Introductionmentioning

confidence: 99%

One-Pot Synthesis and Crystal Structure of Methyl 5-Hydroxy-1-phenyl-1H-pyrazole-3-carboxylate

2012

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Abstract:The title compound, Methyl 5-Hydroxy-1-Phenyl-1H-Pyrazole-3-Carboxylate (C 11 H 10 N 2 O 3 ), was prepared by a one-pot, two-component reaction of an equimolar mixture of phenyl hydrazine and dimethyl acetylene dicarboxylate (DMAD) at reflux temperature for 2 h in a mixture of toluene and dichloromethane as solvent. C 11 H 10 N 2 O 3 was crystallized from an ethanol solution in monoclinic space group P2 1 /c with unit cell dimensions a = 9.5408(16), b = 9.5827(16), c = 11.580(2) Å, β = 105.838(3)°, V = 1018.5(3) Å 3 , Z = 4.

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Sulfide‐Catalyzed Diastereoselective Spirocyclopropanation: Constructing Spiro‐cyclopropanyl‐pyrazolones From α‐Arylidenepyrazolones

Zhao

et al. 2021

Asian J Org Chem

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An efficient and diastereoselective [2 + 1] annulation of arylidenepyrazolones with bromides has been developed that relies on in situ formation of sulfur ylide via a direct sulfide-catalyzed process. A variety of spirocyclopropanyl pyrazolones were achieved in good to excellent yields (up to 93% yield) with high diastereoselectives (up to 20 : 1 dr). Meanwhile, several spirocyclopropanyl compounds were also prepared from corresponding enones. This catalytic strategy exhibits good functional group tolerance, gram-scale capacity and broad substrate scope, and provides various spirocyclopropanyl derivatives.

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Synthesis and hypoglycemic evaluation of substituted pyrazole-4-carboxylic acids

Cited by 193 publications

References 14 publications

Mild and efficient oxidation of 2-pyrazolines and isoxazolines by trans-3,5-dihydroperoxy-3,5-dimethyl-1,2-dioxalane–NH4Cl–HOAc in water–MeCN

Mild and efficient oxidation of 2-pyrazolines and isoxazolines by trans-3,5-dihydroperoxy-3,5-dimethyl-1,2-dioxalane–NH4Cl–HOAc in water–MeCN

One-Pot Synthesis and Crystal Structure of Methyl 5-Hydroxy-1-phenyl-1H-pyrazole-3-carboxylate

Sulfide‐Catalyzed Diastereoselective Spirocyclopropanation: Constructing Spiro‐cyclopropanyl‐pyrazolones From α‐Arylidenepyrazolones

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