Abstract
A novel bifunctional periodic mesoporous organosilica supported isatin-Schiff-base/manganese complex [BPMO@ISB/Mn(II)] is prepared, characterized and its catalytic performance is investigated in the synthesis of dihydropyrano[3,2-c]chromene derivatives. The BPMO@ISB was prepared via grafting of 3-aminopropyltrimethoxysilane (APTS) on a phenylene based PMO followed by treatment with isatin. The BPMO@ISB was then reacted with Mn(NO3)2·4H2O to afford the BPMO@ISB/Mn(II) nanocatalyst. This catalyst was characterized using Fourier transform infrared (FT-IR) spectroscopy, thermal gravimetric analysis (TGA), energy-dispersive X-ray (EDX) spectroscopy, scanning electron microscopy (SEM), low angle powder X-ray diffraction (LAPXRD) analysis and transmission electron microscopy (TEM). The BPMO@ISB/Mn(II) nanocatalyst was successfully used in one-pot synthesis of 3,4-dihydropyrano[c]chromene derivatives at room temperature. In addition, the stability, recyclability and reusability of designed nanocatalyst were studied under applied conditions.
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References
Zhang Y, Zhao Y, Xia C (2009) J Mol Catal A 306(1–2):107–112
Wight A, Davis M (2002) Chem Rev 102:3589–3614 102
Nikoorazm M, Ghorbani-Choghamarani A, Noori N, Tahmasbi B (2016) Appl Organomet Chem 30:843–851
Zhang L, Feng C, Gao S, Wang Z, Wang C (2015) Catal Commun 61:21–25
Jin M, Park J-N, Shon JK, Kim JH, Li Z, Park Y-K, Kim JM (2012) Catal Today 185:183–190
Ghosh S, Dey R, Ahammed S, Ranu BC (2014) Clean Technol Environ Policy 16:1767–1771
Veisi H, Kordestani D, Faraji AR (2014) J Porous Mater 21:141–148
Díaz U, Brunel D, Corma A (2013) Chem Soc Rev 42:4083–4097
Inagaki S, Guan S, Fukushima Y, Ohsuna T, Terasaki O (1999) J. Am. Chem. Soc. 9611-14 121
Asefa T, MacLachlan MJ, Coombs N, Ozin GA (1999) Nature 402:867–871
Melde BJ, Holland BT, Blanford CF, Stein A (1999) Chem Mater 11:3302–3308
Stein A (2003) Adv Mater 15:763–775
Wahab MA, Beltramini JN (2015) RSC Adv 5:79129–79151
Hatton B, Landskron K, Whitnall W, Perovic D, Ozin GA (2005) Acc Chem Res 38:305–312
Hunks WJ, Ozin GA (2005) J Mater Chem 15:3716–3724
Yaghoubi A, Dekamin MG (2017) Chem Sel 2:9236–9243
Dekamin MG, Arefi E, Yaghoubi A (2016) RSC Adv 6:86982–86988
Yaghoubi A, Dekamin MG, Karimi B (2017) Catal Lett 147:2656–2663
Xia LY, Zhang MQ, Rong MZ, Xu WM (2010) Phys Chem Chem Phys 12:10569–10576
Olkhovyk O, Pikus S, Jaroniec M (2005) J Mater Chem 15:1517–1519
Alauzun J, Mehdi A, Reyé C, Corriu RJ (2007) J Mater Chem 17:349–356
Johnson-White B, Zeinali M, Shaffer KM, Patterson CH, Charles PT, Markowitz MA (2007) Biosens Bioelectron 22:1154–1162
Inagaki S, Guan S, Yang Q, Kapoor MP, Shimada T (2008) Chem Commun. https://doi.org/10.1039/b714163g
Takeda H, Goto Y, Maegawa Y, Ohsuna T, Tani T, Matsumoto K, Shimada T, Inagaki S (2009) Chem Commun 6032–6034
Modak A, Mondal J, Aswal VK, Bhaumik A (2010) J Mater Chem 20:8099–8106
Fryxell GE, Liu J, Hauser TA, Nie Z, Ferris KF, Mattigod S, Gong M, Hallen RT (1999) Chem Mater 11:2148–2154
Lu Y, Fan H, Doke N, Loy DA, Assink RA, LaVan DA, Brinker CJ (2000) J Am Chem Soc 122:5258–5261
Liu A, Hidajat K, Kawi S, Zhao D (2000) Chem Commun 13:1145–1146
Walcarius A, Mercier L (2010) J Mater Chem 20:4478–4511
Wang W, Grozea D, Kohli S, Perovic DD, Ozin GA (2011) ACS Nano 5:1267–1275
Moorthy MS, Park S-S, Fuping D, Hong S-H, Selvaraj M, Ha C-S (2012) J Mater Chem 22:9100–9108
Karimi B, Khorasani M, Bakhshandeh Rostami F, Elhamifar D, Vali H (2015) ChemPlusChem 80:990–999
Veisi H, Azadbakht R, Saeidifar F, Abdi MR (2017) Catal Lett 147:976–986
Sadeghzadeh SM (2016) Catal Lett 146:2555–2565
Hajjami M, Rahmani S (2015) J Porous Mater 22:1265–1274
Hajjami M, Kolivand S (2016) Appl Organomet Chem 30:282–288
Hajjami M, Shiri L, Jahanbakhshi A (2015) Appl Organomet Chem 29:668–673
Modak A, Mondal J, Bhaumik A (2012) Green Chem 14:2840–2855
Modak A, Nandi M, Bhaumik A (2012) Catal Today 198:45–51
Verma S, Nandi M, Modak A, Jain SL, Bhaumik A (2011) Adv Synth Catal 353:1897–1902
Horiuchi Y, Do Van D, Yonezawa Y, Saito M, Dohshi S, Kim T-H, Matsuoka M (2015) RSC Adv 5:72653–72658
Zhu F-X, Wang W, Li H-X (2011) J Am Chem Soc 133:11632–11640
Huang J, Zhu F, He W, Zhang F, Wang W, Li H (2010) J Am Chem Soc 132:1492–1493
Yang Q, Liu J, Zhang L, Li C (2009) J Mater Chem 19:945–1955
Hoffmann F, Fröba M (2011) Chem Soc Rev 40:608–620
Sasidharan M, Bhaumik A (2013) ACS Appl Mater Interfaces 5:2618–2625
Elhamifar D, Karimi B, Moradi A, Rastegar J (2014) ChemPlusChem 79:1147–1152
Wahab MA, Kim I, Ha C-S (2004) J Solid State Chem 177:3439–3447
Elhamifar D, Nasr-Esfahani M, Karimi B, Moshkelgosha R, Shábani A (2014) ChemCatChem 6:2593–2599
Na W, Wei Q, Lan J-N, Nie Z-R, Sun H, Li Q-Y (2010) Microporous Mesoporous Mater 134:72–78
Elhamifar D, Kazempoor S, Karimi B (2016) Catal Sci Technol 6:4318–4326
Elhamifar D, Kazempoor S (2016) J Mol Catal A 415:74–81
Shylesh S, Wagener A, Seifert A, Ernst S, Thiel WR (2010) Angew Chem Int Ed 49:184–187
Wei Q, Liu L, Nie Z-R, Chen H-Q, Wang Y-L, Li Q-Y, Zou J-X (2007) Microporous Mesoporous Mater 101:381–387
Cho E-B, Kim D, Jaroniec M (2009) Langmuir 25:13258–13263
Foye W (1991) Padova, Italy 416
Wu JY-C, Fong W-F, Zhang J-X, Leung C-H, Kwong H-L, Yang M-S, Li D, Cheung H-Y (2003) Eur J Pharmacol 473:9–17
Raj T, Bhatia RK, Sharma M, Saxena A, Ishar M (2010) Eur J Med Chem 45:790–794
Rueping M, Sugiono E, Merino E (2008) Chemistry A 14:6329–6332
Moon D-O, Kim K-C, Jin C-Y, Han M-H, Park C, Lee K-J, Park Y-M, Choi YH, Kim G-Y (2007) Int Immunopharmacol 7:222–229
Konkoy C, Fick D, Cai S, Lan N, Keana J, Int PCT (2000) Appl WO 0075123:2001, p. 29313a Chem. Abstr
Shaterian H, Oveisi A (2011) J Iran Chem Soc 8:545–552
Brahmachari G, Banerjee B (2013) ACS Sustain Chem Eng 2:411–422
Elhamifar D, Elhamifar D, Shojaeipoor F (2017) J Mol Catal A 426:198–204
Elhamifar D, Ardeshirfard H (2017) J Colloid Interface Sci 505:1177–1184
Elhamifar D, Yari O, Karimi B (2017) J Colloid Interface Sci 500:212–219
Elhamifar D, Badin P, Karimipoor G (2017) J Colloid Interface Sci 499:120–127
Elhamifar D, Ramazani Z, Norouzi M, Mirbagheri R (2018) J Colloid Interface Sci 511:392–401
Norouzi M, Elhamifar D, Mirbagheri R, Ramazani Z (2018) J Taiwan Inst Chem Eng 89:234–244
Elhamifar D, Shabani A (2014) Chem Eur J 20:3212–3217
Dekamin MG, Alikhani M, Javanshir S (2016) Green Chem Lett Rev 9:96–105
Dekamin MG, Peyman SZ, Karimi Z, Javanshir S, Naimi-Jamal MR, Barikani M (2016) Int J Biol Macromol 87:172–179
Khurana JM, Nand B, Saluja P (2010) Tetrahedron 66:5637–5641
Khan AT, Lal M, Ali S, Khan MM (2011) Tetrahedron Lett 52:5327–5332
Pore D, Undale K, Dongare B, Desai U (2009) Catal Lett 132:104–108
Abdolmohammadi S, Balalaie S (2007) Tetrahedron Lett 48:3299–3303
Dekamin MG, Eslami M, Maleki A (2013) Tetrahedron 69:1074–1085
Abdollahi-Alibeik M, Nezampour F (2013) React Kinet Mech Catal 108:213–229
Moghaddas M, Davoodnia A (2015) Res Chem Intermed 41:4373–4386
Esmaeilpour M, Javidi J, Dehghani F, Dodeji FN (2015) RSC Adv 33(5):26625
Niknam K, Jamali A (2012) Chin J Catal 33:1840–49
Sedaghat M, Booshehri MR, Nazarifar M, Farhadi F (2014) Appl Clay Sci 95:55–59
Tabatabaeian K, Heidari H, Mamaghani M, Mahmoodi NO (2012) Appl Organomet Chem 26:56–61
Tayebee R, Pejhan A, Ramshini H, Maleki B, Erfaninia N, Tabatabaie Z, Esmaeili E (2018) Appl Organomet Chem 32:e3924
Khoobi M, Ma’mani L, Rezazadeh F, Zareie Z, Foroumadi A, Ramazani A, Shafiee A (2012) J Mol Catal A 359:74–80
Hojati SF, Amiri A, MoeiniEghbali N, Mohamadi S (2018) Appl Organomet Chem 32(4):e4235
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The authors thank the Yasouj University and the Iran National Science Foundation (INSF) for supporting this work.
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Norouzi, M., Elhamifar, D. Phenylene and Isatin Based Bifunctional Mesoporous Organosilica Supported Schiff-Base/Manganese Complex: An Efficient and Recoverable Nanocatalyst. Catal Lett 149, 619–628 (2019). https://doi.org/10.1007/s10562-019-02653-6
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DOI: https://doi.org/10.1007/s10562-019-02653-6