Green synthesis of novel phosphonate derivatives using ultrasonic irradiation
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Green synthesis of novel phosphonate derivatives using ultrasonic irradiation Shirin Sharafian1, Zinatossadat Hossaini1*, Faramarz Rostami-Charati1,2, Mohammad A. Khalilzadeh1 1
Department of Chemistry, Qaemshahr Branch, Islamic Azad University, Qaemshahr, Iran; e-mail: [email protected] 2 Research Center for Conservation of Culture Relics, Research Institute of Cultural Heritage & Tourism, Tehran, Iran Published in Khimiya Geterotsiklicheskikh Soedinenii, 2020, 56(10), 1283–1291
Submitted November 25, 2019 Accepted after revision July 9, 2020
A novel and efficient procedure for the generation of quinazolinone phosphonate derivatives employing the reaction of euparin, isatin or its derivatives, primary amines, dialkyl acetylenedicarboxylates, trimethyl phosphite or triphenyl phosphite, and acidic solution of hydrogen peroxide in aqueous media at ambient temperature under ultrasonic irradiation was developed. Without ultrasonic irradiation, the reaction does not proceed and agitation of the reaction mixture is difficult. Some advantages of this procedure are: short time of reaction, high yields of products, easy isolation of products. Keywords: euparin, isatin, primary amines, multicomponent reaction, ultrasonic irradiation.
Many diverse sonochemistry-based procedures have been developed recently.1 Sonochemistry is as an original and valuable method attracting increasing interest for accelerating organic reactions.2–5 Luche and coworkers have carried out a number of investigations which provided the basis for using sonochemistry in organic synthesis6–9 offering significant features for organic reactions such as improvement of reaction rates, formation of pure products with high yields and easier process, energy saving, and waste decreasing when compared with traditional methods.10,11 In our previous work,12 we prepared phosphonate in H2O under conventional conditions at high temperature and with long reaction time, but under ultrasonic irradiation we managed to improve the course of the reaction in H2O in terms of chemoselectivity and economic issues.12,13 On the other hand, optically active phosphonates are valuable compounds,14,15 displaying wide range of biological activity, including anti-influenza,16 antipsoriatic,17 antibiotic,18 antibacterial,19 enzyme inhibiting,20 and herbicidal.21–23 Many approaches to the synthesis of 0009-3122/20/56(10)-1283©2020 Springer Science+Business Media, LLC
organophosphorus compounds exist and are described in current literarute.24–31 Another structural moiety that was targeted in this study was quinazolinone framework. Quinazolinones are important compounds with pharmacological and biological activities such as antifungal,32 antibacterial,33 and antitumor.34 Because of these important properties, different procedures have been reported in literature for producing quinazolinone derivatives.35–41 Herein, in continuation of previous works42,43 and our studies for discovering new synthetic methodologies, in this research, a series of novel phosphonate derivatives containing q
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