Email this article 
Hide
Show all
OPEN ACCESS | 
PEER-REVIEWED |
RESEARCH ARTICLE
|
DOWNLOAD PDF
|
VIEW FULL-TEXT PDF
| TOTAL VIEWS
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 | Revised: 29 May 2014 | Accepted: 13 Jun 2014 | Published: 31 Dec 2014 | Issue Date: December 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.
Announcements
One of our sponsors will cover the article processing fee for all submissions made between May 17, 2023 and June 16, 2023 (Voucher code: SPONSOR2023).
Editor-in-Chief
European Journal of Chemistry
Keywords
Full Text:
PDF
DOI: 10.5155/eurjchem.5.4.577-583.1039
Links for Article
| | | | | | |
| | | | | | |
| | | |
Related Articles
Article Metrics
This Abstract was viewed 1443 times |
PDF Article downloaded 890 times
Citations
[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
[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]. Lyudmila Kayukova, Anna Vologzhanina, Pavel Dorovatovskii, Gulnur Baitursynova, Elmira Yergaliyeva, Ayazhan Kurmangaliyeva, Zarina Shulgau, Sergazy Adekenov, Zhanar Shaimerdenova, Kydymolla Akatan
Reaction Products of β-Aminopropioamidoximes Nitrobenzenesulfochlorination: Linear and Rearranged to Spiropyrazolinium Salts with Antidiabetic Activity
Molecules 27(7), 2181, 2022
DOI: 10.3390/molecules27072181
[4]. Thoraya A. Farghaly, Sami A. Al-Hussain, Magdi E. A. Zaki, Nadia T. Al-Qurashi, Salwa S. Alharbi, Zeinab A. Muhammad
A Review Article on Synthesis of Different Types of Bioactive Spiropyrazole Derivatives
Polycyclic Aromatic Compounds , 1, 2022
DOI: 10.1080/10406638.2022.2105911
[5]. 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
[6]. 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
References
[1]. Berquist, P. R.; Wells, R. J. Chemical and Biological Perspectives, vol. 5, Academic Press, New York, 1993, pp. 1-50.
[2]. Encarnacion, R. D.; Sandoval, E.; Malmstrom, J.; Christophersen, C. J. Nat. Prod. 2000, 63, 874-875.
http://dx.doi.org/10.1021/np990489d
[3]. James, D. M.; Kunze, H. B.; Faulkner, D. J. J. Nat. Prod. 1991, 54, 1137-1140.
http://dx.doi.org/10.1021/np50076a040
[4]. Girgis, A. S.; Ibrahim, Y. A.; Mishriky, N.; Lisgarten, J. N.; Potterc; B. S.; Palmer, R. A. Tetrahedron 2001, 57, 2015-2019.
http://dx.doi.org/10.1016/S0040-4020(01)00020-5
[5]. Fisera, L.; Sauter, F.; Frohlich, J.; Feng, Y.; Ertl, P.; Mereiter, K. Monatsh. Chem. 1994, 125, 553-563.
http://dx.doi.org/10.1007/BF00811848
[6]. Fisera, L.; Sauter, F.; Frohlich, J.; Feng, Y.; Mereiter, K. Monatsh. Chem. 1994, 125, 909-919.
http://dx.doi.org/10.1007/BF00812705
[7]. Strauss, A.; Otto, H. H. Helv. Chim. Acta, 1997, 80, 1823-1830.
http://dx.doi.org/10.1002/hlca.19970800606
[8]. Stverkova, S.; Zak, Z. J. Liebigs Ann. Chem. 1995, 477-480.
http://dx.doi.org/10.1002/jlac.199519950365
[9]. Riyadh, S. M.; Farghaly, T. A. Tetrahedron 2012, 68(44), 9056-9060.
http://dx.doi.org/10.1016/j.tet.2012.08.064
[10]. Padwa, A. 1,3-Dipolar cycloaddition reactions, Vol. 1, Wiley: New York, 1984, pp. 291.
[11]. Girgis, A. S.; Ibrahim, Y. A.; Mishriky, N.; Lisgarten, J. N.; Potter, B. S.; Palmer, R. A. Tetrahedron 2001, 57(10), 2015-2019.
http://dx.doi.org/10.1016/S0040-4020(01)00020-5
[12]. Lee, H. H.; Cain, B. F.; Denny, W. A. J. Org. Chem. 1989, 54, 428-431.
http://dx.doi.org/10.1021/jo00263a032
[13]. Claramunt, R. M.; Elguero. J. Org. Prep. Proced. Int. 1991, 23, 273-320.
http://dx.doi.org/10.1080/00304949109458208
[14]. Havaldar, F. H.; Fernandes, P. S. J. Indian Chem. Soc. 1988, 65, 691-694.
[15]. Sachchar, S. P.; Singh, A. K. J. Indian Chem. Soc. 1985, 62, 142-146.
[16]. Sangwan, N. K.; Dhindsa, K. S.; Malik, O. P.; Malik, M. S. Chim. Acta Turc. 1983, 11, 65-72.
[17]. Berenson, H. (American Cyanamid Co.), U. S. 3, 947, 583 (Cl. 242-273; A01N), 30 Mar. 1976; Chem. Abstr. 85, 1211 (1976).
[18]. Satti, N. K.; Suri, K. A.; Suri, O. P. Indian Drugs 1987, 24, 492-493.
[19]. Fauran, C.; Turin, M. G.; Pourrias, B. (Delalande, S. A.), Fr. Demande 2, 259, 590 (Cl. A61 K, C07D), 29 Aug. 1975; Chem. Abstr. 84, 59477 (1976).
[20]. Sawhney, S. N.; Dhindsa, G. S.; Vir, D. J. Indian Chem. Soc. 1988, 65, 643-645.
[21]. Reis, H.; Vilhuber, H. G.; Schulz, L.; Leuke, D. (BASF A. -G.), Ger. Offen. 2, 525, 024 (Cl. C07D403/12), 30 Dec. 1976; Chem. Abstr. 86, 140042 (1977).
[22]. Bruno, O.; Ranise, A.; Bondavalli, F.; Schenone, P. Farmaco 1992, 47, 1235-1248.
[23]. Vinge, E.; Bjoerkman, S. Acta Pharmacol. Toxicol. 1986, 59, 165-174.
http://dx.doi.org/10.1111/j.1600-0773.1986.tb00150.x
[24]. Bailey, D. M.; Hansen, P. E.; Hlavac, A. G.; Baizman, E. R.; Pearl, J.; De Felice, A. F.; Feigenson, M. E. J. Med. Chem. 1985, 28, 256-260.
http://dx.doi.org/10.1021/jm00380a020
[25]. Farghaly, T. A.; Abdallah, M. A.; Abdel Aziz, M. R. Molecules 2012, 17, 14625-14636.
http://dx.doi.org/10.3390/molecules171214625
[26]. Farghaly, T. A.; Gomha, S. M.; Abbas, E. M. H.; Abdalla, M. M. Arch. Pharm. Chem. Life Sci. 2012, 345, 117-122.
http://dx.doi.org/10.1002/ardp.201100212
[27]. Farghaly, T. A.; Hassaneen, H. M. E. Arch. Pharm. Res. 2013, 36, 564-572.
http://dx.doi.org/10.1007/s12272-013-0045-2
[28]. Farghaly, T. A.; Mahmoud, H. K. Arch. Pharm. Chem. Life Sci. 2013, 346, 392-402.
http://dx.doi.org/10.1002/ardp.201200486
[29]. Farghaly, T. A.; Riyadh, S. M.; Abdallah, M. A.; Ramadan, M. A. Acta. Chim. Slov. 2011, 58, 87-94.
[30]. Ariens, E. J.; Drug Design, Vol. 1., Ariens, E. J.; Editor. P. 1. Academic Press, New York, 1971.
http://dx.doi.org/10.1016/B978-0-12-060302-2.50008-7
[31]. Saint-Ruf, G.; Buu-Hoi, N. P.; Jacouignon, P. J. Chem. Soc. 1960, 35(8), 2690-2694.
http://dx.doi.org/10.1039/jr9600002690
[32]. Wolkoff, P. Can. J. Chem. 1975, 53(9), 1333-1335.
http://dx.doi.org/10.1139/v75-183
[33]. Hassaneen, H. M.; Hilal, R. H.; Elwan, N. M.; Harhash, A.; Shawali, A. S. J. Heterocyclic Chem. 1984, 21, 1013-1016.
http://dx.doi.org/10.1002/jhet.5570210417
[34]. Hassaneen, H. M.; Mousa, H. A. H.; Abed, N. M.; Shawali, A. S. Heterocycles 1988, 27, 695-706.
http://dx.doi.org/10.3987/COM-87-4381
[35]. Holder, I. A.; Boyce, S. T. Burns 1994, 20, 426‐429.
http://dx.doi.org/10.1016/0305-4179(94)90035-3
[36]. Agwa, H.; Aly, M. M.; Bonaly, R. J. Union Arab. Biol. 2000, 7, 62‐82.
[37]. Doughari, J. H. Trop. J. Pharm. Res. 2006, 5, 597‐603.
[38]. Midgley, G.; Clayton, Y.; Hay, J. Diagnosis in color medical mycology, international, UK. Mosby-Year Book, 1997, pp. 14‐17.
[39]. Shiriling, E. M.; Gottlieb, D. Int. J. Syst. Bact. 1966, 16, 313‐340.
http://dx.doi.org/10.1099/00207713-16-3-313
[40]. Girgis, A. S.; Osman, F. H.; El-Samahy, F. A.; Ahmed-Farag. I. S.; Chem. Pap. 2006, 60, 237-242.
http://dx.doi.org/10.2478/s11696-006-0042-8
[41]. Boudriga, S.; Askri, M.; Gharbi, R.; Rammah, M.; Ciamala, K. J. Chem. Res. (S) 2003, 2003, 204-207.
[42]. Girgis, A. S.; Ismail, N. S. M.; Farag, H.; George, R. F.; Eur. J. Med. Chem. 2010, 45, 4229-4238.
http://dx.doi.org/10.1016/j.ejmech.2010.06.018
[43]. Girgis, A. S.; Farag, H.; Ismail, N. S. M.; George, R. F. Eur. J. Med. Chem. 2011, 46, 4964-4969.
http://dx.doi.org/10.1016/j.ejmech.2011.07.058
[44]. Girgis, A. S.; Ibrahim, Y. A.; Farag, A. I. S.; Mishriky, N. J. Chem. Res. (S), 2000, 2000, 508-509.
[45]. Becke, A. D. Phys. Rev. A 1988, 38, 3098-3100.
http://dx.doi.org/10.1103/PhysRevA.38.3098
[46]. Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652.
[47]. Johnson, B. G.; Frisch, M. J. Chem. Phys. Lett. 1993, 216, 133-140.
http://dx.doi.org/10.1016/0009-2614(93)E1238-C
[48]. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785-789.
http://dx.doi.org/10.1103/PhysRevB.37.785
[49]. McLean, A. D.; Chandler. G. S.; Chandler, G. S. J. Chem. Phys. 1980, 72, 5639-5648.
http://dx.doi.org/10.1063/1.438980
[50]. Raghavachari, K.; Binkley, J. S.; Seeger, R.; Pople.; J. A. J. Chem. Phys. 1980, 72, 650-654.
[51]. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A.; Nakatsuji, H.; Caricato, M.; Li, X.; Hratchian, H. P.; Izmaylov, A. F.; Bloino, J.; Zheng, G.; Sonnenberg, J. L.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Vreven, T.; Montgomery, J. A.; Peralta, Jr.; J. E.; Ogliaro, F.; Bearpark, M.; Heyd, J. J.; Brothers, E.; Kudin, K. N.; Staroverov, V. N.; Keith, T.; Kobayashi, R.; Normand, J.; Raghavachari, K.; Rendell, A.; Burant, J. C.; Iyengar, S. S.; Tomasi, J. M.; Cossi, N.; Rega, J. M.; Millam, M.; Klene, J. E.; Knox, J. B.; Cross, V.; Bakken, C.; Adamo, J.; Jaramillo, R.; Gomperts, R. E.; Stratmann, O.; Yazyev, A. J.; Austin, R.; Cammi, C.; Pomelli, J. W.; Ochterski, R. L.; Martin, K.; Morokuma, V. G.; Zakrzewski, G. A.; Voth, P.; Salvador, J. J.; Dannenberg, S.; Dapprich, A. D.; Daniels, O.; Farkas, J. B.; Foresman, J. V.; Ortiz, J.; Cioslowski, D. J.; Fox, Gaussian, Inc.; Wallingford CT, 2010.
[52]. GaussView, Version 5, R. Dennington, T. Keith, J. Millam, Semichem Inc.; Shawnee Mission KS, 2009.
How to cite
The other citation formats (EndNote | Reference Manager | ProCite | BibTeX | RefWorks) for this article can be found online at: How to cite item
DOI Link: https://doi.org/10.5155/eurjchem.5.4.577-583.1039
| 
| 
| 
| 
| 
| 
| 
| 
| 
| 
| 
| 
| 
| 
| 
Save to Zotero
Save to Mendeley
European Journal of Chemistry 2014, 5(4), 577-583 | doi: https://doi.org/10.5155/eurjchem.5.4.577-583.1039 | Get rights and content
Refbacks
- There are currently no refbacks.
Copyright (c)
© Copyright 2010 - 2023 • Atlanta Publishing House LLC • All Right Reserved.
The opinions expressed in all articles published in European Journal of Chemistry are those of the specific author(s), and do not necessarily reflect the views of Atlanta Publishing House LLC, or European Journal of Chemistry, or any of its employees.
Copyright 2010-2023 Atlanta Publishing House LLC. All rights reserved. This site is owned and operated by Atlanta Publishing House LLC whose registered office is 2850 Smith Ridge Trce Peachtree Cor GA 30071-2636, USA. Registered in USA.