Efficient synthesis of pyrano[2,3-d]pyrimidinone and pyrido[2,3-d]pyrimidine derivatives in presence of novel basic ionic liquid catalyst

doi:10.1016/S1872-2067(17)62827-4

Abstract

Abstract:

A basic ionic liquid, namely 1,1'-(butane-1,4-diyl)bis(1,4-diazabicyclo[2.2.2]octan-1-ium) hydrox-ide, was prepared and characterized using Fourier-transform infrared spectroscopy, ¹H nuclear magnetic resonance spectroscopy, and pH measurements. The ionic liquid was used for efficient promotion of the synthesis of pyrano[2,3-d]pyrimidinone and pyrido[2,3-d]pyrimidine derivatives at room temperature under grinding conditions. A simple procedure, short reaction time, high yields, non-column chromatographic separation, commercial availability of the starting materials, and recyclability of the catalyst are attractive features of this process.

Key words: Basic catalyst, Multicomponent reaction, Pyrimidine derivative, Grinding

Omid Goli Jolodar, Farhad Shirini, Mohadeseh Seddighi. Efficient synthesis of pyrano[2,3-d]pyrimidinone and pyrido[2,3-d]pyrimidine derivatives in presence of novel basic ionic liquid catalyst[J]. Chinese Journal of Catalysis, 2017, 38(7): 1245-1251.

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URL: https://www.cjcatal.com/EN/10.1016/S1872-2067(17)62827-4

https://www.cjcatal.com/EN/Y2017/V38/I7/1245

References

[1] A. Mulik, D. Chandam, P. Patil, D. Patil, S. Jagdale, M. Deshmukh, J. Mol. Liq., 2013, 179, 104-109.
[2] J. M. Xu, B. K. Liu, W. B. Wu, C. Qian, Q. Wu, X. F. Lin, J. Org. Chem., 2006, 71, 3991-3993.
[3] A. R. Hajipour, F. Rafiee, J. Iran. Chem. Soc., 2009, 6, 647-678.
[4] K. Niknam, N. Borazjani, R. Rashidian, A. Jamali, Chin. J. Catal., 2013, 34, 2245-2254.
[5] S. I. Alqasoumi, A. M. Al-Taweel, A. M. Alafeefy, E. Noaman, M. M. Ghorab, Eur. J. Med. Chem., 2010, 45, 738-744.
[6] A. D. Broom, J. L. Shim, G. L. Anderson, J. Org. Chem., 1976, 41, 1095-1099.
[7] A. A. Joshi, C. L. Viswanathan, Anti-Infect. Agents Med. Chem., 2006, 5, 105-122.
[8] M. M. Ghorab, A. Y. Hassan, Phosphorus, Sulfur Silicon Relat. Elem., 1998, 141, 251-261.
[9] P. Sharma, N. Rane, V. K. Gurram, Bioorg. Med. Chem. Lett., 2004, 14, 4185-4190.
[10] A. B. A. El-Gazzar, H. N. Hafez, G. A. M. Nawwar, Eur. J. Med. Chem., 2009, 44, 1427-1436.
[11] R. Gupta, A. Jain, R. Joshi, M. Jain, Bull. Korean Chem. Soc., 2011, 32, 899-904.
[12] M. M. Hanna, Eur. J. Med. Chem., 2012, 55, 12-22.
[13] S. V. Shinde, W. N. Jadhav, N. N. Karade, Orient. J. Chem., 2010, 26, 307-317.
[14] R. B. Lichtner, G. Hutchinson, K. Hellmann, Eur. J. Cancer Clin. On-col., 1989, 25, 945-951.
[15] J. I. DeGraw, P. H. Christie, W. T. Clowell, F. M. Sirotnak, J. Med. Chem., 1992, 35, 320-324.
[16] H. D. Thomas, K. Saravanan, L. Z. Wang, M. J. Lin, J. S. Northen, H. Barlow, M. Barton, D. R. Newell, R. J. Griffin, B. T. Golding, N. J. Cur-tin, Mol. Cancer Ther., 2009, 8, 1828-1837.
[17] J. P. De la Cruz, A. Moreno, F. Mérida, J. García-Campos, F. S. de la Cuesta, Pharmacol. Toxicol., 1994, 75, 250-254.
[18] N. C. Petal, A. G. Mehta, Asian J. Chem., 2001, 13, 1385-1388.
[19] B. S. Holla, M. Mahalinga, M. S. Karthikeyan, P. M. Akberali, N. S. Shetty, Bioorg. Med. Chem., 2006, 14, 2040-2047.
[20] S. Calus, E. Gondek, A. Danel, B. Jarosz, M. Pokladko, A. V. Kityk, Mater. Lett., 2007, 61, 3292-3295.
[21] M. Bararjanian, S. Balalaie, B. Movassagh, A. M. Amani, J. Iran. Chem. Soc., 2009, 6, 436-442.
[22] M. M. Heravi, A. Ghods, K. Bakhtiari, F. Derikvand, Synth. Commun., 2010, 40, 1927-1931.
[23] J. Yu, H. Q. Wang, Synth. Commun., 2005, 35, 3133-3140.
[24] S. Balalaie, S. Abdolmohammadi, H. R. Bijanzadeh, A. M. Amani, Mol. Divers., 2008, 12, 85-91.
[25] J. Azizian, A. Shameli, S. Balalaie, M. M. Ghanbari, S. Zomorod-bakhsh, M. Entezari, S. Bagheri, G. Fakhrpour, Orient. J. Chem., 2012, 28, 327-332.
[26] G. M. Ziarani, S. Faramarzi, S. Asadi, A. Badiei, R. Bazl, M. Amanlou, DARU J. Pharm. Sci., 2013, 21, 3.
[27] A. Mobinikhaledi, M. A. B. Fard, Acta. Chim. Slov., 2010, 57, 931-935.
[28] S. Mashkouri, M. R. Naimi-Jamal, Molecules, 2009, 14, 474-479.
[29] H. Kefayati, M. Valizadeh, A. Islamnezhad, Anal. Bioanal. Electro-chem., 2014, 6, 80-90.
[30] O. Goli-Jolodar, F. Shirini, M. Seddighi, J. Iran. Chem. Soc., 2016, 13, 457-463.
[31] A. M. Rad, M. Mokhtary, Int. Nano Lett., 2015, 5, 109-123.