European Journal of Chemistry 2013, 4(3), 195-202 | doi: https://doi.org/10.5155/eurjchem.4.3.195-202.777 | Get rights and content

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Synthesis of some new spirocyclic β-lactam and spirocyclic thiazolidin-4-one derivatives


Nadia Ali Ahmed Elkanzi (1,*) , Hisham Abdallah Abd El-Monem Yosef (2) , Nesrin Mahmoud Morsy Mohamed (3)

(1) Chemistry Department, Faculty of Science, Al Jouf University, Al Jouf, 2014, Kingdom of Saudi Arabia
(2) Department of Organometallic and Organometalloid Chemistry, National Research Centre, Dokki, 12622, Cairo, Egypt
(3) Chemistry Department, Aswan-Faculty of Science, Aswan University, Aswan, 81528, Egypt
(*) Corresponding Author

Received: 19 Mar 2013 | Revised: 19 Apr 2013 | Accepted: 19 Apr 2013 | Published: 30 Sep 2013 | Issue Date: September 2013

Abstract


Selective oxidation of 4-amino-2-methyl-5,10-dioxo-1,5,10,10a-tetrahydrobenzo[g]-quinoline-3-carbonitrile (1) with selenium dioxide provided, 4-amino-2-formyl-5,10-dioxo-1,5,10,10a-tetrahydrobenzo[g]quinoline-3-carbonitrile (2). The one-pot reaction of compound 2 with ethyl cyanoacetate and thiourea in ethanol yielded 4-amino-2-(5-cyano-6-oxo-2-thioxo-1,2,3,6-tetrahydropyrimidin-4-yl)-5,10-dioxo-1,5,10,10a-tetrahydrobenzo[g]-quinoline-3-carbonitrile (3). The cycloaddition reaction of chloroacetic acid with compound 3 yielded 7-(4-amino-3-cyano-5,10-dioxo-1,5,10,10a-tetrahydrobenzo-[g]quinolin-2-yl)-3,5-dioxo-3,5-dihydro-2H-thiazolo[3,2-a]pyrimidine-6-carbonitrile (4). Moreover, Ehrlich-Sachs condensation reaction of compound 4 with the aromatic nitroso compounds 5a-c gave the corresponding new Schiff bases 6a-c. Staudinger's ketene-imine cycloaddition reaction of compounds 6a-c with chloroacetyl chloride afforded the corresponding spiro[chloroazetidinethiazolopyrimidine] derivatives, 7a-c. On the otherhand, cycoladdition reaction of thioglycolic acid with Schiff bases 6a-c yielded the corresponding spiro[thiazolidinethiazolopyrimidine] derivatives, 8a-c. Structures of the new compounds were elucidated by compatible analytical and spectroscopic (IR, 1H NMR and MS) measurements. Moreover, the reaction mechanisms that account for formation of the synthesized compounds have been discussed.

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Keywords


Schiff bases; Benzoquinolines; Spirocyclic β-lactams; Reaction mechanisms; Spirocyclic thiazolidin-4-ones; Spectroscopic measurements

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DOI: 10.5155/eurjchem.4.3.195-202.777

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Funding information


Department of Chemistry, Aswan-Faculty of Science, Aswan University, Aswan, 81528, Egypt

Citations

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[1]. Jacek Młochowski, Halina Wójtowicz-Młochowska
Developments in Synthetic Application of Selenium(IV) Oxide and Organoselenium Compounds as Oxygen Donors and Oxygen-Transfer Agents
Molecules  20(6), 10205, 2015
DOI: 10.3390/molecules200610205
/


References


[1]. Alcaide, B.; Almendros, P.; Aragoncillo, C. Chem. Rev. 2007, 107, 4437-4492.
http://dx.doi.org/10.1021/cr0307300
PMid:17649981

[2]. O'Driscoll, M.; Greenhalgh, K.; Young, A.; Turos, E.; Dickey, S.; Lim, D. V. Bioorg. Med. Chem. 2008, 16, 7832-7837.
http://dx.doi.org/10.1016/j.bmc.2008.06.035
PMid:18672374 PMCid:PMC2617728

[3]. Dugar, S.; Yumibe, N.; Clader, J. W.; Vizziano, M.; Huie, K.; VanHeek, M.; Compton, D. S.; Davis, H. R. J. Bioorg. Med. Chem. Lett. 1996, 6, 1271-1274.
http://dx.doi.org/10.1016/0960-894X(96)00214-4

[4]. Arora, R.; Venugopalan, P.; Bari, S. S. J. Chem. Sci. 2010, 122, 125-135.
http://dx.doi.org/10.1007/s12039-010-0013-z

[5]. Han, W. T.; Trehan, A. K.; Wright, J. J. K.; Federici, M. E.; Seiler, S. M.; Meanwell, N. A. Bioorg. Med. Chem. 1995, 3, 1123-1143.
http://dx.doi.org/10.1016/0968-0896(95)00101-L

[6]. Borthwick, A. D.; Weingarte, G.; Haley, T. M.; Tomaszewski, M.; Wang, W.; HuBedard, Z. J.; Jin, H.; Yuen, L.; Mansour, T. S. Bioorg. Med. Chem. Lett. 1998, 8, 365-370.
http://dx.doi.org/10.1016/S0960-894X(98)00032-8

[7]. Bonneau, P. R.; Hasani, F.; Plouffe, C.; Goamez-Gallego, M.; Malenfant, E.; LaPlante, S. R.; Guse, I.; Ogilvie, W. W.; Plante, R.; Davidson, W. C.; Hopkins, J. L.; Morelock, M. M.; Cordingley, M. G.; Deaziel, R. J. Am. Chem. Soc. 1999, 121, 2965-2973.
http://dx.doi.org/10.1021/ja983905+

[8]. Cainelli, G.; Galletti, P.; Garbisa, S.; Giacomini, D.; Sartor, L.; Quintavalla, A. Bioorg. Med. Chem. 2003, 11, 5391-5399.
http://dx.doi.org/10.1016/j.bmc.2003.09.035
PMid:14642583

[9]. Zhou, N. E.; Guo, D.; Thomas, G.; Reddy, A. V. N.; Kaleta, J.; Purisima, E.; Menard, R.; Micetich, R. G.; Singh, R. Bioorg. Med. Chem. Lett. 2003, 13, 139-141.
http://dx.doi.org/10.1016/S0960-894X(02)00831-4

[10]. Cvetovich, R. J.; Chartran, M .; Hartner, F. W.; Roberge, C.; Amato, J. S.; Grabowski, E. J. J. Org. Chem. 1996, 61, 6575-6580.
http://dx.doi.org/10.1021/jo960618k

[11]. Bittermann, H.; Gmeiner, P. J. Org. Chem. 2006, 71, 97-102.
http://dx.doi.org/10.1021/jo0517287
PMid:16388623

[12]. Alonso, E.; Del Pozo, C.; Gonzalez, J. Synlett. 2002, 69-72.
http://dx.doi.org/10.1055/s-2002-19326

[13]. Skiles, J. W.; McNeil, D. Tetrahedron Lett. 1990, 31, 7277-7280.
http://dx.doi.org/10.1016/S0040-4039(00)88543-3

[14]. Sheehan, J. C.; Chacko, E.; Lo, Y. S.; Ponzi, D. R.; Sato, E. J. Org. Chem. 1978, 43, 4856-4859.
http://dx.doi.org/10.1021/jo00419a031

[15]. Veinberg, G.; Shestakova, I.; Vorona, M.; Kenepe, I.; Lukevics, E. Bioorg. Med. Chem. Lett. 2004, 14, 147-150.
http://dx.doi.org/10.1016/j.bmcl.2003.09.078
PMid:14684317

[16]. Sperka, T.; Pitlik, J.; Bagossi, P.; Tozser, J. Bioorg. Med. Chem. Lett. 2005, 15, 3086-3090.
http://dx.doi.org/10.1016/j.bmcl.2005.04.020
PMid:15893929

[17]. Saturnino, C.; Fusco, B.; Saturnino, P.; de Martino, G.; Rocco, F.; Lancelot, J. C. Biol. Pharm. Bull. 2000, 23, 654-656.
http://dx.doi.org/10.1248/bpb.23.654
PMid:10823683

[18]. Shetgiri, N. P.; Chitre, A. D. Ind. J. Chem. B 2006, 45, 1308-1311.

[19]. Omar, K.; Geronikaki, A.; Zoumpoulakis, P.; Camoutsis, C.; Sokovic, M.; Ciric, A.; Glamoclija, J. Bioorg. Med. Chem. 2010, 18, 426-432.
http://dx.doi.org/10.1016/j.bmc.2009.10.041
PMid:19914077

[20]. Patel, R. B.; Desai, P. S.; Desai, K. R.; Chikhalia, K. H. Indian J. Chem. B 2006, 45, 773-778.

[21]. Turgut, Z.; Yolacan, C.; Aydogan, F.; Bagdatli, E.; Ocal, N. Molecules 2007, 12, 2151-2159.
http://dx.doi.org/10.3390/12092151
PMid:17962733

[22]. Previtera, T.; Vigorita, M. G.; Bisila, M.; Orsini, F.; Benetolla, F.; Bombieri, G. Eur. J. Med. Chem. 1994, 29, 317-324.
http://dx.doi.org/10.1016/0223-5234(94)90102-3

[23]. Srivastava, S.; Jain, A.; Srivastava, S. J. Indian Chem. Soc. 2006, 83, 1118-1123.

[24]. Havrylyuk, D.; Mosula, L.; Zimenkovsky, B.; Vasylenko, O.; Gzella, A.; Lesyk, R. Eur. J. Med. Chem. 2010, 45(11), 5012-5021.
http://dx.doi.org/10.1016/j.ejmech.2010.08.008
PMid:20810193

[25]. Vigorita, M. G.; Ottana, R.; Monforte, F.; Maccari, R.; Trovato, A.; Monforte, M. T.; Taviano, M. F. Biorg. Med. Chem. Lett, 2001, 11, 2791-2794.
http://dx.doi.org/10.1016/S0960-894X(01)00476-0

[26]. Abdel-Moty, S. G.; Abdel-Rahman, M. H.; Elsherief, H. A.; Kafafy, A. H. N. Bull. Pharm. Sci. (Assiut Univ.) 2005, 28, 79-93.

[27]. Vlahov, R.; Parushev, St.; Vlahov, J.; Nickel, P.; Snatzke, G. Pure Appl. Chem. 1990, 62, 1303-1306.
http://dx.doi.org/10.1351/pac199062071303

[28]. Normand-Bayle, M.; Benard, C.; Zouhiri, V.; Mouscadet, J.; Leh, H.; Thomas, C.; Mbemba, G.; Desmaele, D.; Dangelo, J. Bioorg. Med. Chem. Lett. 2005, 15, 4019-4022.
http://dx.doi.org/10.1016/j.bmcl.2005.06.036
PMid:16002283

[29]. Hazeldine, S. T.; Polin, L.; Kushner, J.; White, K.; Corbett, T. H.; Biehl, J.; Horwitz, J. P. Bioorg. Med. Chem. 2005, 13, 1069-1081.
http://dx.doi.org/10.1016/j.bmc.2004.11.034
PMid:15670915

[30]. He, J.; Yun, L.; Yang, R.; Xiao, Z.; Cheng, J.; Zhou, W.; Zhang, Y. Bioorg. Med. Chem. Lett. 2005, 15, 2980-2985.
http://dx.doi.org/10.1016/j.bmcl.2005.04.040
PMid:15908212

[31]. Goda, F. E.; Abdel-Aziz, A. A.; Ghoneim, H. A. Bioorg. Med. Chem. 2005, 13, 3175-3183.
http://dx.doi.org/10.1016/j.bmc.2005.02.050
PMid:15809153

[32]. Savini, L.; Chiasserini, L.; Pellerano, C.; Filippelli, W.; Falcone, G. Farmaco 2001 56, 939-945.

[33]. Khalafallah, A. K.; Abd El-Aal, R. M.; Elkanzi, N. A. A. J. Chin. Chem. Soc. 2002, 49, 387-396.

[34]. Khalafallah, A. K.; Elkanzi, N. A. A.; Soleiman, H. A.; Younis, M. Phosphorous Sulfur 2006, 181, 2483-2503.
http://dx.doi.org/10.1080/10426500600754760

[35]. El-Kanzi, N. A. A. IOSR J. Appl. Chem. 2012, 1(1), 18-30.
http://dx.doi.org/10.9790/5736-0111830

[36]. Tagawa, Y.; Yamashita, K.; Higuchi, Y.; Goto, Y. Heterocycles, 2003, 60(4), 953-957.
http://dx.doi.org/10.3987/COM-02-9702

[37]. Silverstein, R. M.; Bassler, G. C.; Morrill, T. C. Spectrometric Identification of Organic Compounds, 5th ed, John Wiley& Sons. New York (1991).

[38]. Miller, D. D.; Li, W.; Wang, Z.; Lu, Y.; Chen, J.; Dalton, J. T.; Li, C. US Patent 2009/0326020 A1 (2009).

[39]. Ghozlan, S. A. S.; Hassanien, A. A. Tetrahedron 2002, 58, 9423-9429.
http://dx.doi.org/10.1016/S0040-4020(02)01220-6

[40]. Tupare, S. D.; Bhagat, D. V.; Dakea, S. A.; Pawar, R. P. Int. J. Chem. Sci. 2012, 10(4), 1837-1843.

[41]. Ehrlich, P.; Sachs, F. Ber. Dtsch. Chem. Ges. 1899, 32, 2341-2346.
http://dx.doi.org/10.1002/cber.189903202172

[42]. Anderson, D. M. W.; Duncan, G. L. J. Chem. Soc. 1961, 1631-1635.
http://dx.doi.org/10.1039/jr9610001631

[43]. Staudinger, H. Justus Liebigs Ann. Chem. 1907, 356, 51-123.
http://dx.doi.org/10.1002/jlac.19073560106

[44]. Palomo, C.; Aizpurua, J. M.; Ganboa, I.; Oirabide, M. Eur. J. Org. Chem. 1999, 8, 3223-3235.
http://dx.doi.org/10.1002/(SICI)1099-0690(199912)1999:12<3223::AID-EJOC3223>3.0.CO;2-1

[45]. Van der Steen, F. H.; Van Koten, G. Tetrahedron 1991, 47, 7503-7524.
http://dx.doi.org/10.1016/S0040-4020(01)88276-4

[46]. Jiao, L.; Liang, Y.; Xu, J. J. Am. Chem. Soc. 2006, 128, 6060-6069.
http://dx.doi.org/10.1021/ja056711k
PMid:16669675

[47]. Singh, G. S. Tetrahedron, 2003, 59, 7631-7649.
http://dx.doi.org/10.1016/S0040-4020(03)01099-8

[48]. Youssef, M. M.; Amin, M. A. Molecules 2012, 17, 9652-9667.
http://dx.doi.org/10.3390/molecules17089652
PMid:22890170


How to cite


Elkanzi, N.; Yosef, H.; Mohamed, N. Eur. J. Chem. 2013, 4(3), 195-202. doi:10.5155/eurjchem.4.3.195-202.777
Elkanzi, N.; Yosef, H.; Mohamed, N. Synthesis of some new spirocyclic β-lactam and spirocyclic thiazolidin-4-one derivatives. Eur. J. Chem. 2013, 4(3), 195-202. doi:10.5155/eurjchem.4.3.195-202.777
Elkanzi, N., Yosef, H., & Mohamed, N. (2013). Synthesis of some new spirocyclic β-lactam and spirocyclic thiazolidin-4-one derivatives. European Journal of Chemistry, 4(3), 195-202. doi:10.5155/eurjchem.4.3.195-202.777
Elkanzi, Nadia, Hisham Abdallah Abd El-Monem Yosef, & Nesrin Mahmoud Morsy Mohamed. "Synthesis of some new spirocyclic β-lactam and spirocyclic thiazolidin-4-one derivatives." European Journal of Chemistry [Online], 4.3 (2013): 195-202. Web. 28 Nov. 2021
Elkanzi, Nadia, Yosef, Hisham, AND Mohamed, Nesrin. "Synthesis of some new spirocyclic β-lactam and spirocyclic thiazolidin-4-one derivatives" European Journal of Chemistry [Online], Volume 4 Number 3 (30 September 2013)

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