Synthesis of quinazolinones and benzazoles utilizing recyclable sulfated metal-organic framework-808 catalyst in glycerol as green solvent

Yen H. Vo; Thanh V. Le; Hieu D. Nguyen; Tuong A. To; Hiep Q. Ha; Anh T. Nguyen; Anh N.Q. Phan; Nam T.S. Phan

Journal of Industrial and Engineering Chemistry, Vol.64, 107-115, August, 2018

DOI10.1016/j.jiec.2018.03.006 Export Citation

Synthesis of quinazolinones and benzazoles utilizing recyclable sulfated metal-organic framework-808 catalyst in glycerol as green solvent

Yen H. Vo, Thanh V. Le, Hieu D. Nguyen, Tuong A. To, Hiep Q. Ha, Anh T. Nguyen, Anh N.Q. Phan, and Nam T.S. Phan^†

Faculty of Chemical Engineering, HCMC University of Technology, VNU-HCM, 268 Ly Thuong Kiet, District 10, Ho Chi Minh City, Viet Nam, Vietnam

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Zirconium-based metal-organic framework MOF-808 was synthesized, and sulfated with aqueous sulfuric acid. Sulfated MOF-808 was utilized as a recyclable heterogeneous catalyst for the synthesis of quinazolinones from β-ketoesters and benzamides, and for the synthesis of benzimidazoles from β-ketoesters and o-phenylenediamines in glycerol as a green solvent. The sulfated MOF 808 catalyst was more active than many heterogeneous and homogeneous catalysts. The combination of the sulfated MOF-808 and glycerol was also effective for the reaction of o-aminothiophenols with β- diketones or cyclic β-diketones to produce benzothiazoles. To our best knowledge, MOF-based catalysts were not previously utilized as heterogeneous catalyst in glycerol as green solvent.

Keywords:Quinazolinones;Zirconium;Benzazoles;MOF-808;Glycerol

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[3] Zhou ZW, Jia FC, Xu C, Jiang SF, Wu YD, Wu AX, Chem. Commun., 53, 1056 (2017)

[4] Abe T, Kida K, Yamada K, Chem. Commun., 53, 4362 (2017)

[5] Yu ZY, Chen MY, He JX, Tao DJ, Yuan JJ, Peng YY, Song ZB, Mol. Catal., 434, 134 (2017)

[6] Abdel-Jalil RJ, Voelter W, Saeed M, Tetrahedron, 45, 3475 (2004)

[7] Kim NY, Cheon CH, Tetrahedron Lett., 55, 2340 (2014)

[8] Li SS, Qin L, Dong L, Org. Biomol. Chem., 14, 4554 (2016)

[9] Lin WH, Wu WC, Selvaraju M, Sun CM, Org. Chem. Front., 4, 392 (2017)

[10] Gholap AVA, Maity S, Schulzke C, Maiti D, Kapdi AR, Org. Biomol. Chem., 15, 7140 (2017)

[11] Li G, Xie H, Chen J, Guo Y, Deng GJ, Green Chem., 19, 4043 (2017)

[12] Xie C, Han X, Gong J, Li D, Ma C, Org. Biomol. Chem., 15, 5811 (2017)

[13] Li Z, Dong J, Chen X, Li Q, Zhou Y, Yin SF, J. Org. Chem., 80, 9392 (2015)

[14] Hammond C, Green Chem., 19, 2711 (2017)

[15] Szollosi G, Catal. Sci. Technol., 8, 389 (2018)

[16] Zhang S, Wang H, Li M, Han J, Liu X, Gong J, Chem. Sci., 8, 4489 (2017)

[17] Verboekend D, Nuttens N, Locus R, Aelst JV, Verolme P, Groen JC, Perez-Ramirez J, Sels BF, Chem. Soc. Rev., 45, 3331 (2016)

[18] Tulchinsky Y, Hendon CH, Lomachenko KA, Borfecchia E, Melot BC, Hudson MR, Tarver JD, Korzynski MD, Stubbs AW, Kagan JJ, Lamberti C, Brown CM, Dinca M, J. Am. Chem. Soc., 139(16), 5992 (2017)

[19] Yoon T, Bok T, Kim C, Na Y, Park S, Kim KS, ACS Nano, 11, 4808 (2017)

[20] Singh MP, Dhumal NR, Kim HJ, Kiefer J, Anderson JA, J. Phys. Chem. C, 121, 10577 (2017)

[21] Lee SJ, Kim S, Kim EJ, Kim M, Bae YS, J. Chem. Eng., 330, 1012 (2017)

[22] Stewart L, Lu W, Wei ZW, Ila D, Padilla C, Zhou HC, Dalton Trans., 46, 14270 (2017)

[23] Chen J, Zhang Z, Bao Z, Su Y, Xing H, Yang Q, Ren Q, ACS Appl. Mater. Interfaces, 9, 9772 (2017)

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[26] Moon SY, Liu Y, Hupp JT, Farha OK, Angew. Chem.-Int. Edit., 54, 1 (2015)

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[29] Bai Y, Dou Y, Xie LH, Rutledge W, Li JR, Zhou HC, Chem. Soc. Rev., 45, 2327 (2016)

[30] Wang C, Liu X, Demir NK, Chen JP, Li K, Chem. Soc. Rev., 45, 5107 (2016)

[31] Nguyen KD, Kutzscher C, Drache F, Senkovska I, Kaskel S, Inorg. Chem. (2018), doi:http://dx.doi.org/10.1021/acs.inorgchem.7b02854 (in press).

[32] Kuwahara Y, Kango H, Yamashita H, ACS Sustain. Chem. Eng., 5, 1141 (2017)

[33] Caratelli C, Hajek J, Cirujano FG, Waroquier M, Xamena FXLI, Van Speybroeck V, J. Catal., 352, 401 (2017)

[34] Jiang JC, Gandara F, Zhang YB, Na K, Yaghi OM, Klemperer WG, J. Am. Chem. Soc., 136(37), 12844 (2014)

[35] Gu Y, Jerome F, Green Chem., 12, 1127 (2010)

[36] Santoro S, Ferlin F, Luciani L, Ackermann L, Vaccaro L, Green Chem., 19, 1601 (2017)

[37] Liu C, Wang G, Sui W, An L, Si C, ACS Sustain. Chem. Eng., 5, 4690 (2017)

[38] Ingale AP, Patil SM, Shinde SV, Tetrahedron Lett., 58, 4845 (2017)

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[40] Volkringer C, Meddouri M, Loiseau T, Guillou N, Marrot J, Ferey G, Haouas M, Taulelle F, Audebrand N, Latroche M, Inorg. Chem., 47(24), 11892 (2008)

[41] Britt D, Tranchemontagne D, Yaghi OM, PNAS, 33, 11623 (2008)

[42] Haque E, Jun JW, Jhung SH, J. Hazard. Mater., 185, 507 (2011)

[43] Anbia M, Hoseini V, Sheykhi S, J. Ind. Eng. Chem., 18(3), 1149 (2012)

[44] Xia W, Zhu J, Guo W, An L, Xia D, Zou R, J. Mater. Chem. A, 2, 11606 (2014)

[45] Tan K, Nijem N, Canepa P, Gong Q, Li J, Thonhauser T, Chabal YJ, Chem. Mater., 24, 3153 (2012)