Document Type: Original Article

Authors

Department of Chemistry, Mashhad Branch, Islamic Azad University, Mashhad, Iran

Abstract

In this study, a new application of a keplerate-type giant-ball nanoporous isopolyoxomolybdate, (NH4)42[MoVI72MoV60O372(CH3COO)30(H2O)72], denoted as ({Mo132}), in the synthesis of tetrahydrobenzo[a]xanthene-11-ones via a one-pot, three-component reaction of β-naphthol, aryl aldehydes, and dimedone is reported. The reactions were performed under the solvent-free conditions, providing the corresponding products with high atom economy ranging from 90.77% to 92.32%. The catalyst was prepared using inexpensive and readily available materials and could be easily recovered from the reaction mixture by a simple filtration and reused many times with no significant loss of its catalytic activity. High activity of the catalyst, excellent yields, short reaction time, simple procedure with an easy work-up, and the absence of any volatile and hazardous organic solvents are other advantages of the present methodology.

Graphical Abstract

Keywords

[1] Santoro F., Zaccheria F., Shaikh N.I., Ravasio N. Top. Catal., 2012, 55:606

[2] Asif M. Chem. Methodol., 2019, 3:684

[3] Rani G.S., Jyotsna A., Prabhavathi Devi B.L.A. Asian J. Green Chem., 2019, 3:125

[4] Nami N., Tajbakhsh M., Vafakhah M. Iran. Chem. Commun., 2019, 7:93

[5] Davoodnia A., Mahjoobin R., Tavakoli-Hoseini N. Chin. J. Catal., 2014, 35:490

[6] Kargar-Dolatabadi A., Zare A. Chem. Methodol., 2019, 3:655

[7] Aghazadeh M. Prog. Chem. Biochem. Res., 2019, 2:34

[8] Moosavi-Zare A.R., Goudarziafshar H., Jalilian Z. Prog. Chem. Biochem. Res., 2019, 2:59

[9] Karami M., Gholami B., Hekmat-Zadeh T., Zare A. Chem. Methodol., 2019, 3:509

[10] Müller A., Peters F., Pope M.T., Gatteschi D. Chem Rev., 1998, 98:239

[11] Pope M., Müller A. Polyoxometalate Chemistry from Topology via Self‐Assembly to Applications. Netherlands: Kluwer Academic Publishers, 2001

[12] Davoodnia A., Bakavoli M., Barakouhi G., Tavakoli‐Hoseini N. Chin. Chem. Lett., 2007, 18:1483

[13] Ren Y., Wang M., Chen X., Yue B., He H. Materials, 2015, 8:1545

[14] Müller A., Kogerler P., Kuhlmann C. Chem. Commun., 1999, 15:1347

[15] Greedan J.E. J. Mater. Chem., 2001, 11:37

[16] Müller A., Das S.K., Talismanov S., Roy S., Beckmann E., Bogge H., Schmidtmann M., Merca A., Berkle A., Allouche L., Zhou Y., Zhang L. Angew. Chem. Int. Ed., 2003, 42:5039

[17] Müller A., Krickemeyer E., Bögge H., Schmidtmann M., Peters F. Angew. Chem. Int. Ed., 1998, 37:3359

[18] Polarz S., Smarsly B., Goltner C., Antonietti M. Adv. Mater., 2000, 12:1503

[19] Zhang L., Xiong T., Zhou Y., Zhang L. Chem. Asian J., 2010, 5:1984

[20] Song Y., Yang Y., You J., Liu B., Wu L., Hou Y., Wang W., Zhu J. Chem. Pharm. Bull., 2013, 61:167

[21] Wang H., Lu L., Zhu S., Li Y., Cai W. Curr. Microbiol., 2006, 52:1

[22] Banerjee A.G., Kothapalli L.P., Sharma P.A., Thomas A.B., Nanda R.K., Shrivastava S.K., Khatanglekar V.V. Arabian J. Chem., 2016, 9:S480

[23] Iniyavan P., Sarveswari S., Vijayakumar V. Res. Chem. Intermed., 2015, 41:7413

[24] Sethukumar A., Kumar C.U., Prakasam B.A. Phosphorus Sulfur Silicon Relat. Elem., 2013, 188:1652

[25] Akbari A., Hosseini-Nia A. J. Saudi Chem. Soc., 2017, 21:S7

[26] Harichandran G., Amalraj S.D., Shanmugam P. J. Mol. Catal. A: Chem., 2014, 392:31

[27] Soliman H.A., Khatab T.K. Silicon, 2018, 10:229

[28] Zhang Z.H., Wang H.J., Ren X.Q., Zhang Y.Y. Monatsh. Chem., 2009, 140:1481

[29] Ghorbani-Vaghei R., Malaekehpoor S.M. Org. Preparat. Proced. Int., 2010, 42:494

[30] Zakeri M., Heravi M.M., Saeedi M., Karimi N., Oskooie H.A., Tavakoli-Hoseini N. Chin. J. Chem,. 2011, 29:1441

[31] Maleki B., Gholizadeh M., Sepehr Z. Bull. Korean Chem. Soc., 2011, 32:1697

[32] Sudha S., Pasha M.A. Ultrason. Sonochem., 2012, 19:994

[33] Li J.T., Li Y.W., Song Y.L. Synth. Commun., 2012, 42:2161

[34] Olyaei A., Ghodrat Alidoust M. Synth. Commun., 2015, 45:94

[35] Taghavi-Khorasani F., Davoodnia A. Res. Chem. Intermed., 2015, 41:2415

[36] Davoodnia A., Yadegarian S., Nakhaei A., Tavakoli-Hoseini N. Russ. J. Gen. Chem., 2016, 86:2849

[37] Khazaei A., Rezaei M., Moosavi-Zare A.R., Saednia S. J. Chin. Chem. Soc., 2017, 64:1088

[38] Ma J., Peng X., Zhong L., Sun R. New J. Chem., 2018, 42:9140

[39] Tavakoli‐Hoseini N., Davoodnia A. Chin. J. Chem., 2011, 29:203

[40] Emrani A., Davoodnia A., Tavakoli-Hoseini N. Bull. Korean Chem. Soc., 2011, 32:2385

[41] Khashi M., Davoodnia A., Prasada Rao Lingam V.S. Res. Chem. Intermed., 2015, 41:5731

[42] Ameli S., Davoodnia A., Pordel M. Org. Prep. Proced. Int., 2016, 48:328

[43] Hosseininasab N., Davoodnia A., Rostami-Charati F., Khojastehnezhad A. Russ. J. Gen. Chem., 2017, 87:2436

[44] Kazemi E., Davoodnia A., Basafa S., Nakhaei A., Tavakoli-Hoseini N. Adv. J. Chem. A, 2018, 1:96

[45] Nakhaei A., Davoodnia A., Yadegarian S. Iran. Chem. Commun., 2018, 6:334

[46] Teymooria E., Davoodnia A., Khojastehnezhad A., Hosseininasab N. Iran. Chem. Commun., 2019, 7:271

[47] Nakhaei A., Davoodnia A. Chin. J. Catal., 2014, 35:1761

[48] Nakhaei A., Davoodnia A., Morsali A. Res. Chem. Intermed., 2015, 41:7815

[49] Davoodnia A., Nakhaei A., Tavakoli-Hoseini N. Z. Naturforsch. B: J. Chem. Sci., 2016, 71b:219

[50] Nakhaei A., Yadegarian S., Davoodnia A. Heterocycl. Lett., 2016, 6:429

[51] Davoodnia A., Nakhaei A. Synth. React. Inorg. Met. Org. Nano Met. Chem., 2016, 46:1073

[52] Rohaniyan M., Davoodnia A., Nakhaei A. Appl. Organometal. Chem., 2016, 30:626