One pot three component synthesis of 2-amino-4H-chromene derivatives under microwave irradiation using Sr2As2O7 nanocatalyst

Document Type : Original Article

Authors

1 department of inorganic chemistry, faculty of chemistry, urmia university,urmia,iran

2 Inorganic Chemistry Group, Faculty of Chemistry, Semnan University, Semnan, Iran

3 Inorganic Chemistry Group, Faculty of Chemistry, Urmia University, Urmia, Iran

Abstract

2-Amino-4H-chromene compounds are belonged to an important heterocyclic groups that have extensive important in organic chemistry and medicine. The compounds have anti-cancer, anti-bacterial, anti-coagulation and anti-tumor properties and have applications to produce dye, make up and hygienic materials. Until know, several methods have been reported for the synthesis of the compounds. Most of them, suffers defects such as poisoning and volatile solvents, low yield, high length reaction time, and no reusability of used catalyst. In the present work, Sr2As2O7 pyrochlore material was used as a catalyst for the synthesis of 2-amino-4H-cromens derivatives using a three component one-pot synthesis method under microwave irradiation. The raw materials were aromatic aldehydes, malononitrile and beta-naphtol. Sr2As2O7 was synthesized by an ultrasonic assisted solvothermal method using H2O and C2H5OH solvents mixtures at the 1:1 volumetric ratio. The materials were characterized by PXRD, FESEM and FTIR techniques. Then, the catalytic performance of the synthesized nanomaterial was used for the synthesis of 2-amino-4H-chromene derivatives. To do the process, the reaction parameters such as reaction time, solvent type and catalyst amount were optimized and the reactions were performed under the conditions. It was found that the optimum conditions were 15 mg catalyst, H2O as solvent and 6-9 min reaction time.

Keywords


[1] D. Kumar, V. B. Reddy, S. Sharad, S. Kapur, Eur. J. Med. Chem. 44 (2009) 3805.
[2] A. M. M. El-Saghier, M. B. Naili, B. K. Rammash, N. A. Saleh, K. M. Kreddan, ARKIVOC. 16 (2007) 83.
[3] H. Gourdeau, L. Leblond, B. Hamelin, C. Desputeau, K. Dong, I. Kianicka, D. Custeau, C. Bourdeau, L. Geerts, S. X. Cai, J. Drewe, D. Labrecque, S. Kasibhatla, B. Tseng, Mol. Cancer Ther. 3 (2004) 1365.
[4] A. E. F. G. Hammam, O. I. Abd El-Salam, A. M. Mohamed, N. A. Hafez, Indian J. Chem. Sect. B Org. Chem. Incl. Med.Chem. 44 (2005) 1887.
[5] K. Rehse, W. Schinkel, Arch. Pharm. 316 (1983) 988.
[6] J. L. Wang, D. Liu, Z. J. Zhang, S. Shan, X. Han, S. M. Srinivasula, C. M. Croce, E. S. Alnemri, Z. Huang, Proc. Natl. Acad. Sci. USA. 97 (2000) 7124.
[7] M. S. Al-Thebeiti, Boll. Chim. Farm. 140 (2001) 221.
[8] V. B. Vangala, H. Pati, Chem. Method. 2 (2018) 333.
[9] F. K. Behbahani, R. Shahbazi, Chem. Method. 2 (2018) 270.
[10] A.R. Momeni, H. Samimi, H. Vaezzadeh, Chem. Method. 2 (2018) 260.
[11] R. M. N. Kalla, S. J. Byeon, M. S. Heo, I. Kim, Tetrahedron. 69 (2013) 10544.
[12] J. Safari, Z. Zarnegar, J. Mol. Struct. 1072 (2014) 53. 
[13] B. S. Kumar, N. Srinivasulu, R. H. Udupi, B. Rajitha, Y. T. Reddy, P. N. Reddy, P. S. Kumar, J. Heterocyclic Chem. 43 (2006) 1691.
[14] N. V. Lakshmi, S. E. Kiruthika, P. T. Perumal, Synlett. 10 (2011) 1389.
[15] S. R. Kale, S. S. Kahandal, A. S. Burange, M. B. Gawandeb, R. V. Jayaram, Catal. Sci. Technol. 3 (2013) 2050.
[16] M. G. Dekamin, M. Eslami, A. Maleki, Tetrahedron. 69 (2013) 1074.
[17] M. M. Heravi, B. Baghernejad, H. A. Oskooie, J. Chin. Chem. Soc. 55 (2008) 659.
[18] S. M. Vahdat, M. Khavarpour , F. Mohanazadeh,  Journal of Applied Chemistry , 9(2015)41.
[19] J. Cheng, J. Li, C. Ma, Z. Hao, Catalysis Communications. 10 (2009) 1170.
[20] D. J. Haynes, D. A. Berry, D. Shekhawat, J. J. Spivey, Catal. Today. 145 (2009) 121.
[21] B. J. Wuensch, K. W. Eberman, C. Heremans, E. M. Ku, P. Onnerud, E. M. E. Yeo, S. M. Haile, J. K. Stalick, J.D. Jorgensen, Solid State Ionics. 129 (2000) 111.
[22] S. Khademinia, M. Behzad, L. Kafi-Ahmadi, Zeitschrift für anorganische und allgemeine Chemie. 644 (2018) 221.
[23] M. Hasanzadeh Esfahani, M. Behzad, Journal of Applied Chemistry. 15 (2021) 11.
[24] S. Khademinia, M. Behzad, RSC Adv. 5 (2015) 24313.
[25] S. Khademinia, M. Behzad, Adv. Powder Technol. 26 (2015) 644.
[26] M. Weil, Acta Cryst. E. 57 (2001) 28.
[27] C. F. Harvey, K. N. Ashfaque, W. Yu, A. B. M. Badruzzaman, M. A. Ali, P. M. Oates, H. A. Michael, R. B. Neumann, R. Beckie, S. Islam, M. F. Ahmed, Chem. Geol. 228 (2006) 112.
[28] S. Raicevic, V. Stanic, T. Kaludjerovic-Radoicic, Mater. Sci. Forum. 555 (2007) 131.
[29] M. Weil, U. Kolitsch, Poster, Annual Meeting of the DGK, Köln, Germany, February 28 - March 4, Abstract in Z. Kristallogr. Suppl. 22 (2005) 183.
[30] M. Weil, T. drdevic´, C. L. Lengauer, U. Kolitsch, Solid State Sci. 11 (2009) 2111.
[31] A. Mbarek, F. Edhokkar, Acta Cryst. E. 69 (2013) 84.
[32] R. Esmaeili, L. Kafi-Ahmadi, S. Khademinia, J. Molecul. Struct. (2020) DOI: https://doi.org/10.1016/j.molstruc
[33] F. Yousefzadeh, L. Kafi‚ÄĎAhmadi, S. Khademinia, Catal. Lett. (2019) DOI: https://doi.org/10.1007/s10562-019-02733-7.
[34] J. Angel, M. Greena, K. Karuppasamy, R. Antony, X. S. Shajan, S. Kumaresan, Chem. Sci. Trans. 2 (2013) 141.
[35] A. Bishay, C. Maghrabi, Phys. Chem. glasses. 10 (1969) 1.
[36] A. Q. Zhang, M. Zhang, H. H. Chen, J. Chen, H. Y. Chen Synth. Commun. 37 (2007) 231.
[37] K. Gong, H. L. Wang, D. Fang, Z. L. Liu, Catal. Commun. 9 (2008) 650.
[38] H. Mehrabi, N. Kamali, J. Iran. Chemi. Soc. 9 (2012) 599.
[39] A. Mobinikhaledi, H. Moghanian, F. Sasani, Synth. React. Inorg. Met. Org. Chem. 41 (2011) 262.
[40] T. S. Jin, J. C. Xiao, S. J. Wang, T. S. Li, Ultrason. Sonochem. 11 (2004) 393-397.
[41] M. S. Rao, B. S. Chhikara, R. Tiwari, A. N. Shirazi, K. Parang, A. Kumar, Chem. Biol. Interfaces. 2 (2012) 362.
[42] S. Balalaie, S. Ramezanpour, M. Bararjanian, J. H. Gross, Synth. Commun. 38 (2008) 1078.
[43] D. Kumar, V. B. Reddy, B. G. Mishra, R. K. Rana, M. N. Nadagouda, R. S. Varma, Tetrahedron. 63 (2007) 3093.
[44] S. K. Kundu, J. Mondal, A. Bhaumi, Dalton Trans. 42 (2013) 10515.
[45] S. Akocak, B. Sen, N. Lolak, A. Savak, M. Koca, S. Kuzu, F. Sen, Nano-Struct. Nano-Object. 11 (2017) 25.
[46] H. Eshghi, S. Damavandi, G. H. Zohuri, Synth. React.Inorg.Met. 41 (2011) 1067.
[47] S. K. Kundu, A. Bhaumik, Rsc.Adv. 5 (2015) 32730.
[48] B. Sadeghi, E. Arabian, E. Akbarzadeh, Inorg. Nano-Metal Chem. (2020) DOI:10.1080/24701556.2020.1739076.
[49] J. Safari, L. Javadian, Ultrason. Sonochem. 22 (2015) 341.
[50]  S. Taghavi Fardood, A. Ramazani, P. Azimzadeh Asiabi, Y. Bigdeli Fard, B. Ebadzadeh, Asian J. Green Chem. 1 (2017) 34.