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Synthesis of 2-Aryl-2,3-Dihydroquinazolin-4(1H)-One Derivatives Using Lactic Acid as a Green, Natural and Inexpensive Catalyst in Water

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Abstract

In this work, we used lactic acid as a green and inexpensive catalyst for the synthesis of 2,3-dihydro-2-phenylquinazolin-4(1H)-ones via the cyclocondensation of 2-aminobenzamide and aromatic aldehydes in water. The main advantages of this reaction are green conditions, short reaction times, relatively high yields and simple separation of products.

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References

  • Bie Z, Li G, Wang L, Lv Y, Niu J, Gao S (2016) A facile vanadium-catalyzed aerobic oxidative synthesis of quinazolinones from 2-Aminobenzamides with aldehydes or alcohols. Tetrahedron Lett 57(44):4935–4938

    Article  Google Scholar 

  • Coa SL, Feng YP, Jiang YY, Liu SY, Ding GY, Li RT (2005) Synthesis and in vitro antitumor activity of 4(3H)-quinazolinone derivatives with dithiocarbamate side chains. Bioorg Med Chem Lett 15:1915–1917

    Article  Google Scholar 

  • Dar BA, Sahu AK, Patidar P, patial J, Sharma P, Sharma M, Singh B (2012) An easy and efficient protocol for the synthesis of 2,3-dihydroquinazolinones using a low cost and reusable heterogeneous catalyst. Am J Chem 2(5):248–254

    Article  Google Scholar 

  • Edjlali L, Hosseinzdeh-Khanmiri R (2016) γ-alumina catalyzed green synthesis of Pyran’s annulated heterocyclic systems via three-component reaction. Iran J Sci Technol Trans Sci 40(2):151–156

    Article  Google Scholar 

  • Fatahpour M, Hazeri N, Maghsoodlou M, Lashkari M (2016) Lactic acid: a new application as an efficient catalystfor the green one-pot synthesis of 2-Hydroxy-12-aryl-8, 9, 10, 12-Tetrahydrobenzo[a]xanthene-11-one and 12-Aryl-8,9,10,12-Tetrahydrobenzo[a]xanthen-11-one Analogs. Iran J Sci Technol Trans, Sci

    Google Scholar 

  • Ghashang M, Mansoor SS, Aswin K (2015) Synthesis of 2,3-dihydroquinazolin-4(1H)-ones catalyzed by succinimide-N-sulfonic acid as a mild and efficient catalyst. Res Chem Intermed 41(6):3447–3460

    Article  Google Scholar 

  • Giri RS, Thaker HM, Giordano T, Williams J, Rogers D, Sudersanam V, Vasu KK (2009) Design, synthesis and characterization of novel 2-(2,4-disubstituted-thiazole-5-yl)-3-aryl-3H-quinazoline-4-one derivatives as inhibitors of NF-kappaB and AP-1 mediated transcription activation and as potential anti-inflammatory agents. Eur J Med Chem 44(5):2184–2189

    Article  Google Scholar 

  • Habibi-Khorassani SM, Shahraki M, Ebrahimi A, Darijani M (2017) Experimental and theoretical insight into the kinetics and mechanism of the synthesis reaction of 2,3-dihydro-2-phenylquinazolin-4(1H)-one catalyzed in formic acid. Int J Chem Kinet 49(3):157–172

    Article  Google Scholar 

  • Hamel E, Lin CM, Plowman J, Wang HK, Lee KH, Paull KD (1996) Antitumor 2,3-dihydro-2-(aryl)-4(1H)-quinazolinone derivatives: interactions with tubulin. Biochem Pharmacol 51(1):53–59

    Article  Google Scholar 

  • Jafari E, Rahmani Khajouei M, Hassanzadeh F, Hakimelahi GH, Khodarahmi GA (2016) Quinazolinone and quinazoline derivatives: recent structures with potent antimicrobial and cytotoxic activities. Res Pharm Sci 11(1):1–14

    Google Scholar 

  • Maghsoodloua MT, Hazeria N, Fereidoonia E, Salahia S, Mahmoudabadia N, Khorshidia N, Aboonajmib J, Lashkaria M (2015) Chloroacetic acid-promoted heterocyclic reactions: efficient preparation of tetrahydropyridines and 2,3-dihydroquinazolin-4(1H)-ones. Iran Catal 5(3):245–252

    Google Scholar 

  • Maleki A, Aghaei M, Ghamari N, Kamalzare M (2016) Efficient synthesis of 2, 3-dihydroquinazolin-4(1H)-ones in the presence of ferrite/chitosan as a green and reusable nanocatalyst. Int J Nanosci Nanotechnol 12:215–222

    Google Scholar 

  • Noori Sadeh F, Hazeri N, Maghsoodlou M, Lashkari M (2016) Eco-friendly and facile approach toward a one-pot synthesis of 2-Arylpyrrolo[2,3,4-kl]acridin-1(2H)-ones catalyzed by acetic acid under solvent-free conditions. Iran J Sci Technol Trans Sci. https://doi.org/10.1007/s40995-016-0133-5

    Article  Google Scholar 

  • Rostamia A, Tahmasbib B, Gholamib H, Taymorianb H (2013) Supported N-propylsulfamic acid on magnetic nanoparticles used as recoverable and recyclable catalyst for the synthesis of 2,3-dihydroquinazolin-4(1H)-ones in water. Chin Chem Lett 24(3):211–214

    Article  Google Scholar 

  • Safaei HR, Shekouhy M, Shafiee V, Davoodi M (2013) Glycerol based ionic liquid with a boron core: a new highly efficient and reusable promoting medium for the synthesis of quinazolinones. J Mol Liq 180:139–144

    Article  Google Scholar 

  • Safaei HR, Shekouhy Mb, Khademi S, Rahmanian V, Safaei M (2014) Diversity-oriented synthesis of quinazoline derivatives using zirconium tetrakis(dodecylsulfate) [Zr(DS)4] as a reusable Lewis acid-surfactant-combined catalyst in tap water. J Ind Eng Chem 20:3019–3024

    Article  Google Scholar 

  • Safari J, Gandomi-Ravandi S (2013) Environmentally friendly synthesis of 2-aryl-2,3-dihydroquinazolin-4(1H)-ones by novel Co-CNTs as recoverable catalysts. C R Chim 16:1158–1164

    Article  Google Scholar 

  • Safari J, Gandomi-Ravandi S (2014a) Efficient synthesis of 2-aryl-2,3-dihydroquinazolin-4(1H)-ones in thepresence of nanocomposites under microwave irradiation. J Mol Catal A Chem 390:1–6

    Article  Google Scholar 

  • Safari J, Gandomi-Ravandi S (2014b) Silver decorated multi-walled carbon nanotubes as a heterogeneous catalyst in the sonication of 2-aryl-2,3-dihydroquinazolin-4(1H)-ones. RSC Advances 4:11654–11660

    Article  Google Scholar 

  • Shaghayeghi Toosi F, Khakzadi M (2013) A new and facile synthesis 2,3-dihydroquinazolin-4(1H)-ones. Res Chem Intermed 41(1):311–317

    Article  Google Scholar 

  • Sivaguru P, Parameswaran K, Kiruthiga M, Vadivel P, Lalitha A (2014) Synthesis of 2-aryl-2,3-dihydroquinazolin-4(1H)-ones using boric acid-functionalized MCM-41 as a novel heterogeneous catalyst under solvent-free condition. J Iran Chem Soc 12:95–100

    Article  Google Scholar 

  • Xie Z-B, Zhang S-G, Jiang G-F, Sun D-Z, Le Z-G (2015) The green synthesis of 2,3-dihydroquinazolin-4(1H)-ones via direct cyclocondensation reaction under catalyst-free conditions. Green Chem Lett Rev 8(3–4):95–98

    Article  Google Scholar 

  • Zeng LY, Cai C (2010) Iodine: selectively promote the synthesis of mono substituted quinazolin-4(3H)-ones and 2,3-dihydroquinazolin-4(1H)-ones in One-Pot. J Heterocycl Chem 47:1035–1039

    Article  Google Scholar 

  • Zhang ZH, Lu HY, Yang SH, Gao JW (2010) 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 12:643–646

    Article  Google Scholar 

  • Zong-Bo X, Shi-Guo Z, Guo-Fang J, Da-Zhao S, Zhang-Gao L (2015) The green synthesis of 2,3-dihydroquinazolin-4(1H)-ones via direct cyclocondensation reaction under catalyst-free conditions. Green Chem Lett Rev 8:95–98

    Article  Google Scholar 

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Acknowledgements

We gratefully appreciate the financial support from the Research Council of University of Sistan and Baluchestan.

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Correspondence to Malek Taher Maghsoodlou.

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Jazinizadeh, T., Maghsoodlou, M.T. & Heydari, R. Synthesis of 2-Aryl-2,3-Dihydroquinazolin-4(1H)-One Derivatives Using Lactic Acid as a Green, Natural and Inexpensive Catalyst in Water. Iran J Sci Technol Trans Sci 42, 1929–1933 (2018). https://doi.org/10.1007/s40995-017-0362-2

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  • DOI: https://doi.org/10.1007/s40995-017-0362-2

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