Three-component synthesis of 2,3-dihydroquinazilin-4(1H)-ones catalyzed by mesoporous NU-1000 metal-organic framework

Oveisi, Ali Reza; Daliran, Saba

doi:10.22036/cr.2022.347281.1185

Three-component synthesis of 2,3-dihydroquinazilin-4(1H)-ones catalyzed by mesoporous NU-1000 metal-organic framework

Document Type : Original Article

Authors

Ali Reza Oveisi ¹

Saba Daliran ²

¹ Department of Chemistry,, Faculty of Sciences, University of Zabol,

² Department of Chemistry, Faculty of Sciences,, University of Zabol, Zabol, Iran

10.22036/cr.2022.347281.1185

Abstract

In recent years, the synthesis of heterocyclic compounds with biological and pharmacological activities has received much attention In this work, a mesoporous zirconium‐based metal-organic framework (MOF), namely NU-1000 (NU stands for Northwestern University) with a BET surface area of 2100 m2/g was prepared via solvothermal reaction of zirconium chloride, 1,3,6,8-tetrakis(4-carboxyphenyl)pyrene (H4TCPPy) and benzoic acid in dimethylformamide. The structure was characterized by scanning electron microscopy, powder X-ray diffraction, N2 adsorption-desorption and thermogravimetric analysis. Then, due to the high porosity, remarkable thermal and chemical stability of the Zr4+ based MOF, it was used as an heterogeneous catalyst for the synthesis of 2,3-dihydroquinazilin-4(1H)-ones as core structural unit in various biologically active compounds, employing three-component reactions of isatoic anhydride with primary amines (or ammonium acetate) and aldehydes under thermal solvent-free conditions. The solid was stable and reused several times without the loss of any activity in the process. The nanostructure framework consists of octahedral Zr6 clusters with open accessible zirconium Lewis acidic sites. Based on our knowledge, this is the first report on the three-component synthesis of quinazilin-4(1H)-ones by using a mesoporous zirconium metal-organic framework as heterogeneous catalyst.

Graphical Abstract

Three-component synthesis of 2,3-dihydroquinazilin-4(1H)-ones catalyzed by mesoporous NU-1000 metal-organic framework

Keywords

Heterogeneous catalyst

Zr-based metal-organic framework

Mesoporous structures

Nanostructures

Multicomponent reaction

Subjects

Organic Chemistry

[1] O. Yaghi, G. Li, H. Li, Nature. 378, 703 (1995).

[2] X. Han, S. Yang, M. Schröder, Nat. Rev. Chem. 3, 108 (2019).

[3] Z. Yin, S. Wan, J. Yang, M. Kurmoo, M.-H. Zeng, Coord. Chem. Rev. 378, 500 (2019).

[4] S. Karamzadeh, E. Sanchooli, A. R. Oveisi, S. Daliran, R. Luque, Appl. Catal. B: Environ. 303, 120815 (2022).

[5] T. Islamoglu, Z. Chen, M. C. Wasson, C. T. Buru, K. O. Kirlikovali, U. Afrin, M. R. Mian, O. K. Farha, Chem. Rev. 120, 8130 (2020).

[6] S. Rojas, A. Arenas-Vivo, P. Horcajada, Coord. Chem. Rev. 388, 202 (2019).

[7] A. Weddige, J. Prakt. Chem. 31, 124 (1885).

[8] P. Wdowiak, J. Matysiak, P. Kuszta, K. Czarnek, E. Niezabitowska, T. Baj, Front. Chem. 9, 765552 (2021).

[9] V. J. Ram, B. K Farhanullah, Tripathi, and A. K., Srivastava, Biorg. Med. Chem. 11, 2439 (2003).

[10] A. Levitzky, Acc. Chem. Res., 36, 462 (2003).

[11] J.-R Sheu, Cardiovasc. Drug Rev. 17, 237 (1999).

[12] M. Baghbanzadeh, P. Salehi, M. Dabiri, and G. Kozehgary, Synthesis. 2, 344 (2006).

[13] M. Dabiri, P. Salehi, S. Otokesh, M. Baghbanzadeh, G. Kozehgary, and A. A. Mohammadi, Tetrahedron Lett. 46, 6123 (2005).

[14] J. Zhang, D. Ren, Y. Ma, W. Wang, H. Wu, Tetrahedron. 70, 5274 (2014).

[15] M. Dabiri, P. Salehi, M. Baghbanzadeh, M. A. Zolfigol, M. Agheb, and S. Heydari, Catal. Commun. 9, 785 (2008).

[16] L.-M. Wang, L. Hu, J.-H. Shao, J. Yu, and L. Zhang, J. Fluor. Chem. 129, 1139 (2008).

[17] J. E. Mondloch, W. Bury, D. Fairen-Jimenez, S. Kwon, E. J. DeMarco, M. H. Weston, A. A. Sarjeant, S. T. Nguyen, P. C. Stair, R. Q. Snurr, O. K. Farha, and J. T. Hupp, J. Am. Chem. Soc. 135, 10294 (2013).

[18] J. X. Chen, H. Y. Wu, and W. K. Su, Chin. Chem. Lett. 18, 536 (2007).

[19] A. Hassankhani, E. Sanchuli, Chem. Res. 1, 32 (2019)

[20] F. Ahmadian, A. Barmak, E. Ghaderi, et al. J. Iran. Chem. Soc. 16, 2647 (2019).