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Current Organic Chemistry

Editor-in-Chief

ISSN (Print): 1385-2728
ISSN (Online): 1875-5348

Research Article

Microwave-Assisted Regioselective Synthesis of Variously Functionalized [1,2,4]triazolo[3,4-b]quinazolin-5(1H)-ones

Author(s): Awad I. Said, Matti Haukka and Ferenc Fülöp*

Volume 24, Issue 16, 2020

Page: [1892 - 1896] Pages: 5

DOI: 10.2174/1385272824666200814134911

Price: $65

Abstract

[1,2,4]Triazolo[3,4-b]quinazolin-5(1H)-ones with varied functionalization patterns were synthesized in a regioselective manner by reacting 2-thioxo-2,3- dihydroquinazolin-4(1H)-one (2) with variously functionalized hydrazonoyl chlorides (3ah). Linear regioselectivity of the formed products was confirmed by X-ray measurements. Under microwave conditions, the reactions were completed in a few minutes without a change in the regioselectivity.

Keywords: Triazolo[3, 4-b]quinazoline, 2-thioxo-2, 3-dihydroquinazolin-4(1H)-one, hydrazonoyl chlorides, regioselectivity, microwaveassisted reaction, X-ray.

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[1]
Kleeman, A.; Engel, J. Pharmaceutical Substances: Syntheses, Patents and Applications, 4th ed; Thieme: Stuttgart, 2001.
[2]
Auterhoff, H.; Knabe, J.; Höltje, H.D. Lehrbuch der pharmazeutischen Chemie, 14th ed; Wissenschaftliche Verlag: Stuttgart, 1999.
[3]
Selassie, C.D.; Abraham, D.J. Burger’s Medicinal Chemistry and Drug Discovery; John Wiley and Sons: New York, 2003.
[4]
Witt, A.; Bergman, J. Recent developments in the field of quinazoline chemistry. Curr. Org. Chem., 2003, 7, 659-677.
[http://dx.doi.org/10.2174/1385272033486738]
[5]
Mehndiratta, S.; Sapra, S.; Singh, G.; Singh, M.; Nepali, K. Quinazolines as apoptosis inducers and inhibitors: a review of patent literature. Recent Patents Anticancer Drug Discov., 2016, 11(1), 2-66.
[http://dx.doi.org/10.2174/1574892811666151218151506] [PMID: 26681186]
[6]
Fares, M.; Abou-Seri, S.M.; Abdel-Aziz, H.A.; Abbas, S.E.S.; Youssef, M.M.; Eladwy, R.A. Synthesis and antitumor activity of pyrido [2,3-d]pyrimidine and pyrido[2,3-d] [1,2,4]triazolo[4,3-a]pyrimidine derivatives that induce apoptosis through G1 cell-cycle arrest. Eur. J. Med. Chem., 2014, 83, 155-166.
[http://dx.doi.org/10.1016/j.ejmech.2014.06.027] [PMID: 24956552]
[7]
Abdelhamid, A.O.; Gomha, S.M.; Abdelriheem, N.A.; Kandeel, S.M. Synthesis of new 3-heteroarylindoles as potential anticancer agents. Molecules, 2016, 21(7), 929-943.
[http://dx.doi.org/10.3390/molecules21070929] [PMID: 27438822]
[8]
Loev, B.; Musser, J.H.; Brown, R.E.; Jones, H.; Kahen, R.; Huang, F.C.; Khandwala, A.; Goldman, P.S.; Leibowitz, M.J. 1,2,4-Triazolo[4,3-a]quinoxaline-1,4-diones as antiallergic agents. J. Med. Chem., 1985, 28(3), 363-366.
[http://dx.doi.org/10.1021/jm00381a016] [PMID: 2579236]
[9]
Ahmed, M.S.M.; Farghaly, T.A. Antimicrobial activity of [1,2,4]triazolo[4,3-a]pyrimidine and new pyrido[3,2-f][1,4]thiazepine derivatives. Lett. Org. Chem., 2018, 15, 183-190.
[http://dx.doi.org/10.2174/1570178614666171010161751 ]
[10]
Sirakanyan, S.N.; Spinelli, D.; Geronikaki, A.; Kartsev, V.A.; Hakobyan, E.K.; Panosyan, H.A.; Stepanyan, H.M.; Zuppiroli, L.; Hovakimyan, A.A. New cyclopenta[4′,5′]pyrido[3′,2′:4,5]thieno[2,3-e][1,2,4]triazolo[4,3-c]pyri-midines and cyclopenta[4′,5′]pyrido[3′,2′:4,5]thieno[2,3-e][1,2,4]triazolo [1,5-c]pyrimidines: synthesis and antimicrobial activities. Curr. Org. Chem., 2017, 21, 1227-1241.
[http://dx.doi.org/10.2174/1385272821666170222102400 ]
[11]
Sirakanyan, S.N.; Spinelli, D.; Geronikaki, A.; Kartsev, V.A.; Hakobyan, E.K.; Hovakimyan, A.A. Synthesis of new derivatives of heterocyclic systems containing triazolopyrimidine, thiazolo[3,2-a]pyrimidine and pyri-mido[2,1-b]thiazine moiety showing promising antimicrobial activity. Curr. Org. Chem., 2018, 22, 2576-2588.
[http://dx.doi.org/10.2174/1385272822666181122111339]
[12]
Shen, H.; Wang, Q.; Yang, M.; Sun, Z.; Weng, J.; Tan, C.; Wu, H.; Han, L.; Liu, X. Recent advances of 1,2,4-triazolo[3,4-α]pyridines: synthesis and bioactivities. Curr. Org. Chem., 2017, 21, 1626-1650.
[http://dx.doi.org/10.2174/1385272821666170410145554]
[13]
Matiychuk, V.S.; Potopnyk, M.A.; Luboradzki, R.; Obushak, M.D. A new method for the synthesis of 1-aryl-1,2,4-triazole derivatives. Synthesis, 2011, 11, 1799-1813.
[http://dx.doi.org/10.1002/chin.201144126 ]
[14]
Silvestri, R.; Cascio, M.G.; La Regina, G.; Piscitelli, F.; Lavecchia, A.; Brizzi, A.; Pasquini, S.; Botta, M.; Novellino, E.; Di Marzo, V.; Corelli, F. Synthesis, cannabinoid receptor affinity, and molecular modeling studies of substituted 1-aryl-5-(1H-pyrrol-1-yl)-1H-pyrazole-3-carboxamides. J. Med. Chem., 2008, 51(6), 1560-1576.
[http://dx.doi.org/10.1021/jm070566z] [PMID: 18293908]
[15]
Liu, J.; Nie, M.; Wang, Y.; Hu, J.; Zhang, F.; Gao, Y.; Liu, Y.; Gong, P. Design, synthesis and structure-activity relationships of novel 4-phenoxyquinoline derivatives containing 1,2,4-triazolone moiety as c-Met kinase inhibitors. Eur. J. Med. Chem., 2016, 123, 431-446.
[http://dx.doi.org/10.1016/j.ejmech.2016.07.059] [PMID: 27490023]
[16]
Shawali, A.S. Reactions of heterocyclic compounds with nitrilimines and their precursors. Chem. Rev., 1993, 93, 2731-2777.
[http://dx.doi.org/10.1021/cr00024a007]
[17]
Shawali, A.S. A review on bis-hydrazonoyl halides: Recent advances in their synthesis and their diverse synthetic applications leading to bis-heterocycles of biological interest. J. Adv. Res., 2016, 7(6), 873-907.
[http://dx.doi.org/10.1016/j.jare.2016.09.001] [PMID: 27672450]
[18]
Tupychak, M.A.; Shyyka, O.Ya.; Pokhodylo, N.T.; Obushak, M.D. Nitrileimines as an alternative to azides in base-mediated click [3 + 2] cycloaddition with methylene active nitriles. RSC Advances, 2020, 10, 13696-13699.
[http://dx.doi.org/10.1039/D0RA01417F]
[19]
Abdelhamid, A.O.; Shawali, A.S.; Gomha, S.M.; El-Enany, W.M.A. Synthesis and antimicrobial evaluation of some novel thiazole, 1,3,4-thiadiazole and pyrido[2,3-d][1,2,4]triazolo[4,3-a]pyrimidine derivatives incorporating pyrazole moiety. Heterocycles, 2015, 91, 2126-2142.
[http://dx.doi.org/10.3987/COM-15-13319]
[20]
Riyadh, S.M. Enaminones as building blocks for the synthesis of substituted pyrazoles with antitumor and antimicrobial activities. Molecules, 2011, 16(2), 1834-1853.
[http://dx.doi.org/10.3390/molecules16021834] [PMID: 21343888]
[21]
Shehab, W.S. EL-Farargy, A. F.; Abdelhamid, A. O; Aziz, M. A. Synthesis and biological application of pyranopyrimidine derivatives catalyzed by efficient nanoparticles and their nucleoside analogues. Synth. Commun., 2019, 49, 3560-3572.
[http://dx.doi.org/10.1080/00397911.2019.1679538]
[22]
Said, M.A.; Eldehna, W.M.; Nocentini, A.; Bonardi, A.; Fahim, S.H.; Bua, S.; Soliman, D.H.; Abdel-Aziz, H.A.; Gratteri, P.; Abou-Seri, S.M.; Supuran, C.T. Synthesis, biological and molecular dynamics investigations with a series of triazolopyrimidine/triazole-based benzenesulfonamides as novel carbonic anhydrase inhibitors. Eur. J. Med. Chem., 2020, 185, 111843-111855.
[http://dx.doi.org/10.1016/j.ejmech.2019.111843] [PMID: 31718943]
[23]
Abdelrazek, F.M.; Gomha, S.M.; Abdel‐aziz, H.M.; Farghaly, M.S.; Peter, M.; Abdel‐Shafy, A.A. Efficient synthesis and in silico study of some novel pyrido[2,3‐d][1,2,4]triazolo[4,3‐a]pyramid-ine derivatives. J. Heterocycl. Chem., 2020, 57, 1759-1769.
[24]
Chou, S-Y.; Yin, W-K.; Chung, Y-S.; Chang, L-S.; Liu, C-W.; Chen, S-F.; Shih, K-S. Kilogram-scale synthesis of a highly selective α1-adrenoceptor antagonist (DL-028A). Org. Process Res. Dev., 2002, 6, 273-278.
[http://dx.doi.org/10.1021/op0100807]
[25]
Abdelhadi, H.A.; Abdallah, T.A.; Hassaneen, H.M. Synthesis of 1,3-disubstituted 1,2,4-triazolo[4,3-a]quinazolin-5-one derivatives. Heterocycles, 1995, 41, 1999-2005.
[http://dx.doi.org/10.3987/COM-95-7103]
[26]
CrysAlis P.R.O. Rigaku Oxford Diffraction; Yarnton: Oxfordshire, 2015.
[27]
Sheldrick, G.M. Crystal structure refinement with SHELXL. Acta Crystallogr. C Struct. Chem., 2015, 71(Pt 1), 3-8.
[http://dx.doi.org/10.1107/S2053229614024218] [PMID: 25567568]
[28]
Hübschle, C.B.; Sheldrick, G.M.; Dittrich, B. ShelXle: a Qt graphical user interface for SHELXL. J. Appl. Cryst., 2011, 44(Pt 6), 1281-1284.
[http://dx.doi.org/10.1107/S0021889811043202] [PMID: 22477785]

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