European Journal of Chemistry 2014, 5(4), 577-583. doi:10.5155/eurjchem.5.4.577-583.1039

Study on regioselective synthesis of bioactive bis-spiropyrazolines using molecular orbital calculations


Thoraya Abd El-Reheem Farghaly (1,*) , Ikhlass Mohamed Abbas (2) , Walid Mohamed Ibrahim Hassan (3) , Mai Samir Lotfy (4)

(1) Department of Chemistry, Faculty of Science, Cairo University, Giza, 12613, Egypt
(2) Department of Chemistry, Faculty of Science, Cairo University, Giza, 12613, Egypt
(3) Department of Chemistry, Faculty of Science, Cairo University, Giza, 12613, Egypt
(4) Department of Chemistry, Faculty of Science, Cairo University, Giza, 12613, Egypt
(*) Corresponding Author

Received: 02 Mar 2014, Accepted: 13 Jun 2014, Published: 31 Dec 2014

Abstract


1,3-Dipolar cycloaddition reaction of (2E,2'E)-2,2'-(1,4-phenylene bis(methanylylidene)) bis(3,4-dihydronaphthalen-1(2H)-one) (3) and 2,2'-(1,4-phenylene bis(methanylylidene)) bis(1H-indene-1,3(2H)-dione) (8) with a variety of nitrilimines, generated in situ by triethylamine dehydrohalogenation of the corresponding hydrazonoyl halides, (4) proceeded region-selectively and affording novel spiropyrazoline derivatives 5 and 10, respectively. The mechanisms of the reactions studied are discussed and the structures of the products were confirmed by spectral data and elemental analyses. Also, molecular orbital plots for HOMO and LUMO verify our suggested mechanism and stereo-selectivity of the reaction. The antimicrobial activity of the products was evaluated and promising results were obtained.

 


Keywords


Nitrilimine; Regioselectivity; Bis-spiropyrazole; Antimicrobial activity; Molecular orbital calculations; 1,3-Dipolar cycloaddition reaction

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DOI: 10.5155/eurjchem.5.4.577-583.1039

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Citations

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[1]. Zubi Sadiq, Sadia Naz, Erum Akbar Hussain, Umbreen Aslam
Spiropyrazolines: A Worthy Insight into the Recent Strategies and Synthetic Applications
Letters in Organic Chemistry  16(5), 357, 2019
DOI: 10.2174/1570178615666181022141147
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[2]. Fatma A. A. El-Hag, Sobhi M. Gomha, Thoraya A. Farghaly
Hydrazonoyl Halides Precursors to Synthesis of New Thiazole, Thiadiazole, and Benzothiazepine Derivatives
Journal of Heterocyclic Chemistry  54(2), 1172, 2017
DOI: 10.1002/jhet.2688
/


[3]. Yingpeng Su, Yanan Zhao, Bingbing Chang, Xiaolong Zhao, Rong Zhang, Xuan Liu, Danfeng Huang, Ke-Hu Wang, Congde Huo, Yulai Hu
[3 + 2] Cycloaddition of para-Quinone Methides with Nitrile Imines: Approach to Spiro-pyrazoline-cyclohexadienones
The Journal of Organic Chemistry  84(11), 6719, 2019
DOI: 10.1021/acs.joc.9b00434
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[4]. Sobhi M. Gomha, Thoraya A. Farghaly, Abdelwahed R. Sayed
Design, Synthesis, and Characterization of Some Newbis-thiazoles
Journal of Heterocyclic Chemistry  54(2), 1537, 2017
DOI: 10.1002/jhet.2741
/


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How to cite


Farghaly, T.; Abbas, I.; Hassan, W.; Lotfy, M. Eur. J. Chem. 2014, 5(4), 577-583. doi:10.5155/eurjchem.5.4.577-583.1039
Farghaly, T.; Abbas, I.; Hassan, W.; Lotfy, M. Study on regioselective synthesis of bioactive bis-spiropyrazolines using molecular orbital calculations. Eur. J. Chem. 2014, 5(4), 577-583. doi:10.5155/eurjchem.5.4.577-583.1039
Farghaly, T., Abbas, I., Hassan, W., & Lotfy, M. (2014). Study on regioselective synthesis of bioactive bis-spiropyrazolines using molecular orbital calculations. European Journal of Chemistry, 5(4), 577-583. doi:10.5155/eurjchem.5.4.577-583.1039
Farghaly, Thoraya, Ikhlass Mohamed Abbas, Walid Mohamed Ibrahim Hassan, & Mai Samir Lotfy. "Study on regioselective synthesis of bioactive bis-spiropyrazolines using molecular orbital calculations." European Journal of Chemistry [Online], 5.4 (2014): 577-583. Web. 21 Nov. 2019
Farghaly, Thoraya, Abbas, Ikhlass, Hassan, Walid, AND Lotfy, Mai. "Study on regioselective synthesis of bioactive bis-spiropyrazolines using molecular orbital calculations" European Journal of Chemistry [Online], Volume 5 Number 4 (31 December 2014)

DOI Link: https://doi.org/10.5155/eurjchem.5.4.577-583.1039

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