Synthesis of 4-hydrazinopyrazolo[3,4-d]pyrimidines and their Reactions with Carbonyl Compounds

2013 ◽  
Vol 37 (1) ◽  
pp. 6-10 ◽  
Author(s):  
Mastoura M. Edrees
Keyword(s):  
Hydrazine Hydrate ◽  
Carbonyl Compounds ◽  
Pyrazole Derivatives ◽  
Pyrimidine Derivatives ◽  
Pyrazolone Derivatives ◽  
Alkylation Reactions

Synthesis of a new 4-hydrazinopyrazolo[3,4- d]pyrimidine was achieved via heating (4,6-dithioxo-1 H-pyrazolo[3,4- d] pyrimidin-3-yl)acetonitrile with hydrazine hydrate. Reactions of the latter product with thiophene-2-carbaldehyde and ethyl hydrazonoacetoacetate analogues afforded the corresponding hydrazone and pyrazole derivatives, respectively. Similarly, condensation of 2-[6-(benzylsulfanyl)-4-hydrazino-1 H-pyrazolo[3,4- d]pyrimidin-3-yl]acetonitrile with thiophene-2-carbaldehyde and ethyl hydrazonoacetoacetate analogues gave the respective hydrazone and pyrazolone derivatives. Alkylation reactions of 2-[4,6-bis(benzylsulfanyl)-1 H-pyrazolo[3,4- d]pyrimidin-3-yl]acetonitrile with arylamines gave the respective 4-( N-arylamino)-6-benzylsulfanylpyrazolo[3,4- d]pyrimidine derivatives.

Synthesis and Antibacterial Screening of Some Pyrazole Derivatives Catalyzed by Cetyltrimethylammoniumbromide (CTAB)

2020 ◽  
Vol 17 ◽  
Author(s):  
Ravi Bansal ◽  
Pradeep K. Soni ◽  
Neha Gupta ◽  
Sameer S. Bhagyawant ◽  
Anand K. Halve
Keyword(s):  
Hydrazine Hydrate ◽  
Ethyl Acetoacetate ◽  
Aromatic Aldehydes ◽  
Pyrazole Derivatives ◽  
Phenyl Hydrazine ◽  
One Pot ◽  
Antibacterial Screening ◽  
Water As Solvent ◽  
Substituted Pyrazoles ◽  
Sulfinic Esters

Aims: In this article we have developed an eco-friendly one-pot multi-component reaction methodology was employed for the green synthesis of functionalized pyrazole derivatives viz cyclo-condensation of aromatic aldehydes, ethyl acetoacetate and phenyl hydrazine and/or hydrazine hydrate in the presence of cetyltrimethylammoniumbromide (CTAB) at 90°C temperature in aqueous medium. Method: In the present protocol we developed a green method for the synthesis of functionalized pyrazole derivatives through one-pot, multi-component cyclo-condensation of aromatic aldehydes, phenyl hydrazine or hydrazine hydrate and ethyl acetoacetate using cetyltrimethylammoniumbromide (CTAB) as a catalyst in water as solvent. Our methodology confers advantages such as short reaction time, atom economy, purification of product without using column chromatographic and hazardous solvent. The reaction is being catalyzed by cetyltrimethylammoniumbromide (CTAB) and thus products are formed under the green reaction conditions. Results: Initially the reaction of benzaldehyde and phenylhydrazine with ethyl acetoacetate was carried out in water at room temperature in the absence of the catalyst; no product was obtained after 24 h (Table 1 entry 1). When the reaction was carried out using L-proline as catalyst in ethanol at 70°C the yield of product was 20. Conclusion: This research not only provides a green and efficient method for the synthesis of sulfinic esters but also shows new applications of electrochemistry in organic synthesis. We consider that this green and efficient synthetic protocol used to prepare sulfinic esters will have good applications in future. In conclusion, we have developed successfully a green and efficient one-pot multi-component methodology for the synthesis of substituted pyrazoles using CTAB as a catalyst in water as solvent with excellent yields. Purifications of compounds were achieved without the use of traditional chromatographic procedures. This methodology has advantages of operational simplicity, clean reaction profiles and relatively broad scope which make it more attractive for the diversity oriented synthesis of these heterocyclic libraries. In this methodology we suggest the further alternative possibility for formation of substituted pyrazoles. The compound 7h can be used as an anticancer drug in pharma industry.

Cycloaddition versus Alkylation Reactions of 2-Vinylindoles with α,β-Unsaturated Carbonyl Compounds Under Gold Catalysis

2013 ◽  
Vol 2013 (28) ◽  
pp. 6267-6279 ◽  
Author(s):  
Valentina Pirovano ◽  
Monica Dell'Acqua ◽  
Diego Facoetti ◽  
Donatella Nava ◽  
Silvia Rizzato ◽  
...  
Keyword(s):  
Carbonyl Compounds ◽  
Gold Catalysis ◽  
Alkylation Reactions

scholarly journals Studies on Syntheses of Pyrazolone and Pyrazole Derivatives. I. Syntheses of Pyrazolone Derivatives possessing Functional Group at 3-Position

1972 ◽  
Vol 92 (9) ◽  
pp. 1082-1088 ◽  
Author(s):  
SHOJI SUGIURA ◽  
TADASHI KITAMIKADO ◽  
KIHACHIRO IZUMI ◽  
MIKIO HORI ◽  
HAJIME FUJIMURA
Keyword(s):  
Functional Group ◽  
Pyrazole Derivatives ◽  
Pyrazolone Derivatives

Novel benzofurane-pyrazole derivatives with anti-inflammatory, cyclooxygenase inhibitory and cytotoxicity evaluation

2022 ◽  
Vol 0 (0) ◽  
Author(s):  
Zafer Sahin ◽  
Yağmur Özhan ◽  
Hande Sipahi ◽  
Sevde Nur Biltekin ◽  
Leyla Yurttaş ◽  
...  
Keyword(s):  
Hydroxy Ketone ◽  
No Production ◽  
Raw 264.7 ◽  
Pyrazole Derivatives ◽  
H Nmr ◽  
Pyrazolone Derivatives ◽  
Cox 2 ◽  
Anti Inflammatory ◽  
Cox 1 ◽  
C Nmr

Abstract Novel benzofurane-pyrazolone hybrids have been synthesized for evaluating their anti-inflammatory and cytotoxic properties. 4-(2-chloroacetyl)-1,5-dimethyl-2-phenyl-1,2-dihydro-3H-pyrazol-3-one were reacted with α-hydroxy aldehyde or α-hydroxy ketone derivatives to obtain nine novel pyrazolone derivatives. Structures were successfully elucidated by 1H NMR, 13C NMR, IR and HRMS. Enzyme inhibitory activity was measured on cyclooxygenases (COXs) as considered to address anti-inflammatory activity. Compound 2 showed the highest activity on both COX-1 and COX-2 subtypes with 12.0 μM and 8.0 μM IC50, respectively. This activity was found close to indomethacin COX-2 inhibition measured as 7.4 μM IC50. Rest of the compounds (1, 3–9) showed 10.4–28.1 μM IC50 on COX-2 and 17.0–35.6 μM IC50 on COX-1 (Compound 1 has no activity on COX-1). Tested compounds (1–9) showed activity on NO production. Only compound was the 4, which showed a low inhibition on IL-6 levels. Cell viability was up to 60% at 100 μM for all compounds (1–9) on RAW 264.7 and NIH3T3 cell lines, thus compounds were reported to be noncytotoxic.

scholarly journals A Facial Synthesis and Antimicrobial Activity of Some Pyrazole Derivatives Carrying Indole

2010 ◽  
Vol 7 (3) ◽  
pp. 745-750 ◽  
Author(s):  
K. Narasimha Sarma ◽  
M. C. S. Subha ◽  
K. Chowdoji Rao
Keyword(s):  
Antimicrobial Activity ◽  
Acetic Acid ◽  
Carboxylic Acid ◽  
Hydrazine Hydrate ◽  
Elemental Analysis ◽  
Antimicrobial Activities ◽  
Subsequent Treatment ◽  
Spectral Studies ◽  
Pyrazole Derivatives

The title compounds (7a-h) were prepared by esterification of indole-5-carboxylic acid (1) and subsequent treatment with hydrazine hydrate in methanolviathe hydrazide (3). Finally hydrazide (3) condensed with different substituted aldol (6) in acetic acid / PTSA catalytic media produced (3,5-subsituted-4,5-dihydropyrazol-1-yl)(1H-indol-5-yl)methanone (7a-h) in good yields. All the newly synthesized compounds are by elemental analysis and spectral studies and evaluated for antimicrobial activities.

Cycloaddition versus Alkylation Reactions of 2-Vinylindoles with α,β-Unsaturated Carbonyl Compounds Under Gold Catalysis (Eur. J. Org. Chem. 28/2013)

2013 ◽  
Vol 2013 (28) ◽  
pp. n/a-n/a
Author(s):  
Valentina Pirovano ◽  
Monica Dell'Acqua ◽  
Diego Facoetti ◽  
Donatella Nava ◽  
Silvia Rizzato ◽  
...  
Keyword(s):  
Carbonyl Compounds ◽  
Gold Catalysis ◽  
Alkylation Reactions

scholarly journals Microwave Supported Synthesis and Antimicrobial Evaluation of Bis-Pyrazole Derivatives from N-Phenyl Glutarimides

2016 ◽  
Vol 65 ◽  
pp. 53-63
Author(s):  
Ravindra S. Dhivare ◽  
S.S. Rajput
Keyword(s):  
Hydrazine Hydrate ◽  
Solvent Free ◽  
The Novel ◽  
Pyrazole Derivatives ◽  
Antimicrobial Evaluation ◽  
Solvent Free Synthesis

A simple ecofriendly microwave supported solvent free synthesis of bis-chalcones was carried out by the reaction of di-substituted 4-hydroxy-3-methoxy benzaldehyde with different substituted N-phenylpiperidine-2,6-diones in presence of neutral corundum. By the same way the novel bis-pyrazoles were developed from bis-chalcones and hydrazine hydrate with neutral corundum. All the derivatives were characterized and screened their antimicrobial potencies.

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