Efficient protocol for the production of pyrimido[4,5-b] quinolines using an organic-inorganic hybrid catalyst

Dianat, Manije; Zare, Abdolkarim; Hosainpour, Monavvar

doi:10.26655/AJNANOMAT.2021.4.4

Document Type : Original Article

Authors

¹ Department of Chemistry, Payame Noor University, PO Box 19395-3697, Tehran, Iran

² Department of Chemistry, Payame Noor University, PO Box 19395‐3697 Tehran, Iran

https://doi.org/10.26655/AJNANOMAT.2021.4.4

Abstract

In this work, an efficient protocol for the synthesis of pyrimido[4,5-b]quinolines was reported. The one-pot multi-component reaction of arylaldehydes, barbituric acid (or 2-thiobarbituric acid) and anilines in the presence of an organic-inorganic hybrid material namely tetramethyl-N-(silica-n-propyl)-N′-sulfonic acid-ethylenediaminium chloride/mesylate ([TSSECM]) afforded the mentioned compounds. This protocol has several advantages including, high yields (86-95%), relatively short reaction times (110-120 min), recyclability of the catalyst and easy purification of the products without column chromatography.

Graphical Abstract

Keywords

Main Subjects

Catalyst

References

[1]. Nikoorazm M., Khanmoradi M., Mohammadi M. Appl. Organometal. Chem., 2020, 34:e5504

[2]. Pourkazemi A., Nasouri Z., Fakhraie F., Razzaghi A., Parhami A., Zare A. Asian J. Nanosci. Mater., 2020, 3:131

[3]. Kumari P., Yadav R., Bharti R., Parvin T. Mol. Divers., 2020, 24:107

[4]. Majidi Arlan F., Javahershenas R., Khalafy J. Asian J. Nanosci. Mater., 2020, 3:238

[5]. Kumari S., Kumar D., Gajaganti S., Srivastava V., Singh S. Synth. Commun., 2019, 49:431

[6]. Ezzatzadeh E., Sheikholeslami-Farahani F., Yadollahzadeh K., Rezayati S. Comb. Chem. High Throughput Screen., 2021, 24:1465

[7]. Nabi Bidhendi G., Mehrdadi N., Firouzbakhsh M. Chem. Methodol., 2021, 5:271

[8]. Huang P., Chen Y., Lin H., Yu L., Zhang L., Wang L., Zhu Y., Shi J. Biomaterials, 2017, 125:23

[9]. Zhang B., Zhang Y., Wang Z., Yang D., Gao Z., Wang D., Guo Y., Zhu D., Mori T. Dalton Trans., 2016, 45:16561

[10]. Zare A., Dianat M., Eskandari M.M. New J. Chem., 2020, 44:4736

[11]. Sajjadifar S., Amini I., Habibzadeh S., Mansouri G., Ebadi E. Chem. Methodol., 2020, 4:624

[12]. Zafari S., Ghorbani-Vaghei R., Alavinia S. Mater. Chem. Phys., 2021, 270:124840

[13]. Sajjadifar S., Amini I., Mansouri G., Alimohammadi S. Eurasian Chem. Commun., 2020, 2:626

[14]. Khazaei A., Gohari-Ghalil F., Tavasoli M., Rezaei-Gohar M., Moosavi-Zare A.R. Chem. Methodol., 2020, 4:543

[15]. Zare A., Atashrooz J., Eskandari M.M. Res. Chem. Intermed., 2021, 47:1349

[16]. Ezzatzadeh E. Asian J. Nanosci. Mater., 2021, 4:125

[17]. A. Sadeghi Meresht, E. Ezzatzadeh, B. Dehbandi, M. Salimifard, R. Rostamian, Polycycl. Arom. Compd. in press, doi: 10.1080/10406638.2021.1913426

[18]. Ezzatzadeh E., Zamani Hargalani F., Shafaei F. Polycycl. Arom. Compd., in press, doi: 10.1080/10406638.2021.1879882

[19]. Althuis T.H., Moore P.F., Hess H.J. J. Med. Chem., 1979, 22:44

[20]. El-Sayed O.A., El-Baih F.M.E., El-Aqeel S.I., Al Bassam B.A., Hussein M.E. Boll. Chem. Farmac., 2002, 141:461

[21]. Nargund L.V.G., Badiger V.V., Yarnal S.M. J. Pharm. Sci., 1992, 81:365

[22]. Ghorab M.M., Ragab F.A., Heiba H.I., Arafa R.K., El-Hossary E.M. Eur. J. Med. Chem., 2010, 45:3677

[23]. El-Gazzar A.B.A., Hafez H.N., Nawwar G.A.M. Eur. J. Med. Chem., 2009, 44:1427

[24]. Abbas H.A.S., Hafez H.N., El-Gazzar A.-R.B.A. Eur. J. Med. Chem., 2011, 46:21

[25]. Khalafi-Nezhad A., Sarikhani S., Shaikhi Shahidzadeh E., Panahi F. Green Chem., 2012, 14:2876

[26]. Mohire P.P., Patil R.B., Chandam D.R., Jadhav S.J., Patravale A.A., Kumbhar D.R., Ghosh J.S., Deshmukh M.B. Res. Chem. Intermed., 2017, 43:7013

[27]. Reddy S.S., Reddy M.V.K., Reddy P.V.G. ChemistrySelect, 2018, 3:4283

[28]. Mosslemin M.H., Zarenezhad E., Shams N., Soltani Rad M.N., Anaraki-Ardakani H., Fayazipoor R. J. Chem. Res., 2014, 38:169

[29]. Nongthombam G.S., Nongkhlaw R. Synth. Comun., 2018, 48:541

[30]. Nongthombam G.S., Kharmawlong G.K., Kumar J.E., Nongkhlaw R. New J. Chem., 2018, 42:9436

Asian Journal of Nanoscience and Materials

Efficient protocol for the production of pyrimido[4,5-b] quinolines using an organic-inorganic hybrid catalyst

References

References

Volume 4, Issue 4
October 2021
Pages 282-289

Efficient protocol for the production of pyrimido[4,5-b] quinolines using an organic-inorganic hybrid catalyst

References

References

Volume 4, Issue 4October 2021Pages 282-289

Volume 4, Issue 4
October 2021
Pages 282-289