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Combinatorial Chemistry & High Throughput Screening

Author(s): Abdolrahman Keyhani, Mohammad Nikpassand*, Leila Zare Fekri and Hassan Kefayati

DOI: 10.2174/1386207324999210120194730

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One-pot Synthesis of a New Category of 2-aryl-quinazolinones Using OImDSA as an Efficient Heterocyclic Medium

Page: [267 - 273] Pages: 7

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Abstract

Background: Dihydroquinazolinone derivatives are an important family of fused heterocyclic compounds which possess a wide range of biological, medicinal and pharmacological properties such as anti-tumor, anti-biotic, diuretic, analgesic, anti-hypertonic, anti-pyretic, antidepressant, anti-histamine and vasodilation activities.

Introduction: So far, some acid catalysts, e.g. p-toluenesulfonic acid, silica sulfuric acid, zinc(II) perfluorooctanoate, gallium(III) triflate, ionic liquid, Al(H2PO4)3, I2, montmorillonite K-10, Amberlyst-15, Al/Al2O3 and Fe3O4 nanoparticles, have been reported to accomplish this threecomponent reaction. Some of these methods have drawbacks such as toxic solvents and catalysts, long reaction time, the use of expensive catalysts and adverse yields.

Methods: A mixture of benzaldehydes (1mmol), isatoic anhydride (1 mmol), Glycine (1 mmol) and OImDSA (2 mL) were stirred at room temperature for the required reaction times (1-2 h). The progress of the reaction was monitored by TLC (EtOAc: petroleum ether 1:2). After completion of the reaction, as indicated by TLC, the ionic liquid was separated by extraction with 2×15 mL of water. The solid residue was separated by recrystallization from EtOH. The pure products were collected in 86-97% yields.

Results: Herein, we report the mild synthesis of some derivatives of 2-aryl-quinazolin-4(1H)-ones from isatoic anhydride and Glycine using OImDSA, which has been found to be an efficient synthesis method, with depleted side effects, reduced reaction steps, increased efficiency and curtailed reaction time, in continuation of our research on the synthesis of heterocyclic and pharmaceutical compounds.

Conclusion: In conclusion, we have developed a simple, green and efficient protocol for the synthesis of 2-aryl-quinazolin-4(1H)-ones using OImDSA. Simplicity, easy practice, inexpensive, environmentally friendly and reusable ionic liquid are notable attributes of this new method. To the best of our knowledge, this is the first report on the synthesis of a new library of quinazolin-4(1H)- ones derived from Glycine as a natural substrate based on green chemistry conditions.

Keywords: One-pot reaction, 2-aryl-quinazolin-4(1H)-one, Glycine, ionic liquid, synthesis, isatoic anhydride.

Graphical Abstract

[1]
Narasimhulu, M.; Lee, Y.R. Ethylenediamine diacetate-catalyzed three-component reaction for the synthesis of 2, 3-dihydroquinazolin-4(1H)-ones and their spirooxindole derivatives. Tetrahedron, 2011, 67, 9627-6934.
[http://dx.doi.org/10.1016/j.tet.2011.08.018]
[2]
Armarego, W.L.F. Quinazolines. Adv. Heterocycl. Chem., 1979, 24, 1-62.
[http://dx.doi.org/10.1016/S0065-2725(08)60507-3] [PMID: 14087221]
[3]
Shaterian, H.R.; Oveisi, A.R. PPA‐SiO2 as a Heterogeneous Catalyst for Efficient Synthesis of 2‐Substituted‐1,2,3,4‐tetrahydro‐4‐quinazolinones under Solvent‐free Conditions. Chin. J. Chem., 2009, 27, 2418-2422.
[http://dx.doi.org/10.1002/cjoc.201090018]
[4]
Yu, Y.; Ostresh, J.M.; Houghten, R.A. A traceless approach for the parallel solid-phase synthesis of 2-(arylamino)quinazolinones. J. Org. Chem., 2002, 67(16), 5831-5834.
[http://dx.doi.org/10.1021/jo020236g] [PMID: 12153287]
[5]
Kamal, A.; Ramana, K.V.; Ankati, H.B.; Ramana, A.V. Mild and efficient reduction of azides to amines: synthesis of fused [2,1-b]quinazolinones. Tetrahedron Lett., 2002, 43, 6861-6863.
[http://dx.doi.org/10.1016/S0040-4039(02)01454-5]
[6]
Rao, V.B.; Ratnam, C.V. Versatile one-pot synthesis of 2, 3-dihydro-4 (1H)-quinazolinones from isatolic anhydrides and Schiff-bases. Indian J. Chem. B, 1979, 18, 409-412.
[7]
Akazome, M.; Yamamoto, J.; Kondo, T.; Watanabe, Y. Palladium complex-catalyzed intermolecular reductive N-heterocyclization: novel synthesis of quinazoline derivatives from 2-nitrobenzaldehyde or 2-nitrophenyl ketones with formamide. J. Organomet. Chem., 1995, 494, 229-233.
[http://dx.doi.org/10.1016/0022-328X(95)05387-5]
[8]
Wang, L.M.; Hu, L.; Shao, J.H.; Yu, J.; Zhang, L. A novel catalyst zinc(II) perfluorooctanoate [Zn(PFO)2]-catalyzed three-component one-pot reaction: Synthesis of quinazolinone derivatives in aqueous micellar media. J. Fluor. Chem., 2008, 129, 1139-1145.
[http://dx.doi.org/10.1016/j.jfluchem.2008.08.005]
[9]
Baghbanzadeh, M.; Salehi, P.; Dabiri, M.; Kozehgary, G. Water-Accelerated Synthesis of Novel Bis-2,3-dihydroquinazolin-4(1H)-one Derivatives. Synthesis, 2006, 344-348.
[10]
Dabiri, M.; Salehi, P.; Baghbanzadeh, M.; Zolfigol, M.A.; Agheb, M.; Heydari, S. Silica sulfuric acid: An efficient reusable heterogeneous catalyst for the synthesis of 2,3-dihydroquinazolin-4(1H)-ones in water and under solvent-free conditions. Catal. Commun., 2008, 9, 785-788.
[http://dx.doi.org/10.1016/j.catcom.2007.08.019]
[11]
Chen, J.X.; Wu, D.Z.; He, F.; Liu, M.; Wu, H.Y.; Ding, J.C.; Su, W.K. Gallium(III)triflate-catalyzed one-pot selective synthesis of 2,3-dihydroquinazolin-4(1H)-ones and quinazolin-4(3H)-ones. Tetrahedron Lett., 2008, 49, 3814-3818.
[http://dx.doi.org/10.1016/j.tetlet.2008.03.127]
[12]
Chen, J.X.; Su, W.K.; Wu, H.Y.; Liu, M.C.; Jin, C. Eco-friendly synthesis of 2,3-dihydroquinazolin-4(1H)-ones in ionic liquids or ionic liquid–water without additional catalyst. Green Chem., 2007, 9, 972-975.
[http://dx.doi.org/10.1039/b700957g]
[13]
Darvatkar, N.B.; Bhilare, S.V.; Deorukhkar, A.R.; Raut, D.G.; Salunkhe, M.M. [bmim]HSO4: an efficient and reusable catalyst for one-pot three-component synthesis of 2,3-dihydro-4(1H)-quinazolinones. Green Chem. Lett. Rev., 2010, 3, 301-306.
[http://dx.doi.org/10.1080/17518253.2010.485581]
[14]
Shaterian, H.R.; Oveisi, A.R.; Honarmand, M. Synthesis of 2,3-Dihydroquinazoline-4(1H)-ones. Synth. Commun., 2010, 40, 1231-1242.
[http://dx.doi.org/10.1080/00397910903064831]
[15]
Dabiri, M.; Salehi, P.; Bahramnejad, M.; Alizadeh, M. A practical and versatile approach toward a one-pot synthesis of 2,3-disubstituted 4(3H)-quinazolinones. Monatsh. Chem., 2010, 141, 877-881.
[http://dx.doi.org/10.1007/s00706-010-0341-1]
[16]
Salehi, P.; Dabiri, M.; Baghbanzadeh, M.; Bahramnejad, M. One‐Pot, three‐component synthesis of 2,3‐Dihydro‐4(1H)‐quinazolinones by Montmorillonite K‐10 as an efficient and reusable catalyst. Synth. Commun., 2006, 36, 2287-2292.
[http://dx.doi.org/10.1080/00397910600639752]
[17]
Surpur, M.P.; Singh, P.R.; Patil, S.B.; Samant, S.D. Expeditious one‐pot and solvent‐free synthesis of dihydroquinazolin‐4(1H)‐ones in the presence of microwaves. Synth. Commun., 2007, 37, 1965-1970.
[http://dx.doi.org/10.1080/00397910701354699]
[18]
Kassaee, M.Z.; Rostamizadeh, S.; Shadjou, N.; Motamedi, E.; Esmaeelzadeh, M. An efficient one‐pot solvent‐free synthesis of 2,3‐dihydroquinazoline‐4(1H)‐ones via Al/Al2O3 nanoparticles. J. Heterocycl. Chem., 2010, 47, 1421-1424.
[http://dx.doi.org/10.1002/jhet.506]
[19]
Zhang, Z.H.; Lü, H.Y.; Yang, S.H.; Gao, J.W. Synthesis of 2,3-dihydroquinazolin-4(1H)-ones by three-component coupling of isatoic anhydride, amines, and aldehydes catalyzed by magnetic Fe3O4 nanoparticles in water. J. Comb. Chem., 2010, 12(5), 643-646.
[http://dx.doi.org/10.1021/cc100047j] [PMID: 20684507]
[20]
Saffar-Teluri, A.; Bolouk, S. One-pot, three-component synthesis of 2,3-dihydroquinazolin-4(1H)-ones using p-toluenesulfonic acid–paraformaldehyde copolymer as an efficient and reusable catalyst. Monatsh. Chem., 2010, 141, 1113-1115.
[http://dx.doi.org/10.1007/s00706-010-0376-3]
[21]
Rostamizadeh, S.; Amani, A.M.; Mahdavinia, G.H.; Sepehrian, H.; Ebrahimi, S. Synthesis of some novel 2-Aryl-Substituted 2,3-Dihydroquinazolin-4(1H)-ones under solvent-free conditions using MCM-41-SO3H as a highly efficient sulfonic acid. Synthesis, 2010, 1356-1360.
[http://dx.doi.org/10.1055/s-0029-1218676]
[22]
Shahi, A.M.; Nikpassand, M.; Fekri, L.Z. Acidic Ionic Liquid-catalyzed Synthesis of Pyrano[4,3-b]pyran-5(4H)-ones using 4,4,4-trifluoro-1-phenylbutane-1,3-dione as a Building Block. Curr. Org. Synth., 2020, 17(8), 648-653.
[http://dx.doi.org/10.2174/1570179417666200520111536] [PMID: 32433006]
[23]
Nikpassand, M.; Zare Fekri, L.; Gharib, M.; Marvi, O. Fe+3-montmorillonite K-10 as a green and reusable catalyst for the synthesis of new generation of dihydropyrimidinones. Lett. Org. Chem., 2012, 9, 745-748.
[http://dx.doi.org/10.2174/157017812803901917]
[24]
Nikpassand, M.; Pirdelzendeh, D. Green synthesis of novel azo-linked 2-phenyl benzimidazoles using ionic liquid [BDBIMm]Br. Dyes Pigm, 2016, 130, 314-318.
[http://dx.doi.org/10.1016/j.dyepig.2016.03.038]
[25]
Nikpassand, M.; Fekri, L.Z.; Farokhian, P. An efficient and green synthesis of novel benzoxazole under ultrasound irradiation. Ultrason. Sonochem., 2016, 28, 341-345.
[http://dx.doi.org/10.1016/j.ultsonch.2015.08.014] [PMID: 26384917]
[26]
Masoumi Shahi, A.; Nikpassand, M.; Zare Fekri, L. An efficient and green synthesis of new Benzo[f]chromenes Using 1,4-Disulfo-1,4-diazoniabicyclo[2.2.2]octane chloride as a novel medium. Org. Prep. Proced. Int., 2019, 51, 521-529.
[http://dx.doi.org/10.1080/00304948.2019.1666637]
[27]
Mamaghani, M.; Tabatabaeian, K.; Mirzaeinejad, M.; Nikpassand, M. One-pot facile conversion of Baylis-Hillman adducts into 1, 5-diarylpyrazoles using microwave irradiation. J. Iran. Chem. Soc, 2006, 3, 89-92.
[http://dx.doi.org/10.1007/BF03245796]