Tags

Type your tag names separated by a space and hit enter

Synthesis and Antibacterial Screening of Some Pyrazole Derivatives Catalyzed by Cetyltrimethylammoniumbromide (CTAB).
Curr Org Synth. 2020 Jun 20 [Online ahead of print]CO

Abstract

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.

Authors+Show Affiliations

School of Studies in Chemistry, Jiwaji University, Gwalior. India.School of Studies in Chemistry, Jiwaji University, Gwalior. India.School of Studies in Biotechnology, Jiwaji University, Gwalior. India.School of Studies in Biotechnology, Jiwaji University, Gwalior. India.School of Studies in Chemistry, Jiwaji University, Gwalior. India.

Pub Type(s)

Journal Article

Language

eng

PubMed ID

32562527

Citation

Bansal, Ravi, et al. "Synthesis and Antibacterial Screening of some Pyrazole Derivatives Catalyzed By Cetyltrimethylammoniumbromide (CTAB)." Current Organic Synthesis, 2020.
Bansal R, Soni PK, Gupta N, et al. Synthesis and Antibacterial Screening of Some Pyrazole Derivatives Catalyzed by Cetyltrimethylammoniumbromide (CTAB). Curr Org Synth. 2020.
Bansal, R., Soni, P. K., Gupta, N., Bhagyawant, S. S., & Halve, A. K. (2020). Synthesis and Antibacterial Screening of Some Pyrazole Derivatives Catalyzed by Cetyltrimethylammoniumbromide (CTAB). Current Organic Synthesis. https://doi.org/10.2174/1570179417666200620220232
Bansal R, et al. Synthesis and Antibacterial Screening of some Pyrazole Derivatives Catalyzed By Cetyltrimethylammoniumbromide (CTAB). Curr Org Synth. 2020 Jun 20; PubMed PMID: 32562527.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Synthesis and Antibacterial Screening of Some Pyrazole Derivatives Catalyzed by Cetyltrimethylammoniumbromide (CTAB). AU - Bansal,Ravi, AU - Soni,Pradeep K, AU - Gupta,Neha, AU - Bhagyawant,Sameer S, AU - Halve,Anand K, Y1 - 2020/06/20/ PY - 2020/01/15/received PY - 2020/05/06/revised PY - 2020/05/11/accepted PY - 2020/6/21/entrez PY - 2020/6/21/pubmed PY - 2020/6/21/medline KW - Green synthesis KW - Heterocycles KW - antibacterial screening KW - cetyltrimethylammoniumbromide (CTAB). KW - multi-component synthesis KW - one-pot KW - pyrazoles JF - Current organic synthesis JO - Curr Org Synth N2 - 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. SN - 1570-1794 UR - https://www.unboundmedicine.com/medline/citation/32562527/Synthesis_and_Antibacterial_Screening_of_Some_Pyrazole_Derivatives_Catalyzed_by_Cetyltrimethylammoniumbromide__CTAB__ DB - PRIME DP - Unbound Medicine ER -
Try the Free App:
Prime PubMed app for iOS iPhone iPad
Prime PubMed app for Android
Prime PubMed is provided
free to individuals by:
Unbound Medicine.