Three-component reaction of β-keto esters, aromatic aldehydes and urea/thiourea promoted by caffeine: A green and natural, biodegradable catalyst for eco-safe Biginelli synthesis of 3,4-dihydropyrimidin-2-(1H)-ones/tiones derivatives under solvent-free conditions

Farzaneh Mohamadpour, Mojtaba Lashkari

Abstract


Caffeine was found to be a natural and green and biodegradable cat­alyst for the one-pot, three-component condensation Biginelli reaction of β-keto esters, aromatic aldehydes and urea/thiourea to afford the corres­pond­ing 3,4-dihydropyrimidin-2(1H)-ones/thiones derivatives under solvent-free conditions. The remarkable features of this green procedure are high yields, short reaction times, simplicity of operation and work-up procedures, the avail­ability and easy handling of this solid catalyst, avoidance of hazardous or toxic catalysts and organic solvents and economic availability of the catalyst.

Keywords


caffeine; natural and green biodegradable catalyst; Biginelli react¬ion; 3,4-dihydropyrimidin-2(1H)-ones/tihones derivatives; eco-safe procedure; solvent-free conditions

References


B. Pouramiri, M. Shirvani, E. Tavakolinejad Kermani, J. Serb. Chem. Soc. 82 (2017) 483

D. Setamdideh, J. Serb. Chem. Soc. 81 (2016) 971

G. Mohamadi Ziarani, M. Rahimifard, F. Nouri, A. Badiei, J. Serb. Chem. Soc. 80 (2015) 1265

S. Z. Hejazi, A. Fallah Shojaei, K. Tabatabaeian, F. Shirini, J. Serb. Chem. Soc. 80 (2015) 971

F. Mohamadpour, M. T. Maghsoodlou, R. Heydari, M. Lashkari, J. Iran. Chem. Soc. 13 (2016) 1549

F. Mohamadpour, M. T. Maghsoodlou, R. Heydari, M. Lashkari, Res. Chem. Intermed. 42 (2016) 7841

K. Sujatha, P. Shanmugam, P. T. Perumal, D. Muralidharan, M. Rajendran, Bioorg. Med. Chem. Lett. 16 (2006) 4893

S. Wisen, J. Androsavich, C. G. Evans, L. Chang, J. E. Gestwicki, Bioorg. Med. Chem. Lett. 18 (2008) 60

L. Heys, C. G. Moore, P. Murphy, Chem. Soc. Rev. 29 (2000) 57

M. Ashok, B. S. Holla, N. S. Kumara, Eur. J. Med. Chem. 42 (2007) 380

E. W. Hurst, R. Hull, J. Med. Pharm. Chem. 3 (1961) 215

A. M. Magerramow, M. M. Kurbanova, R. T. Abdinbekova, I. A. Rzaeva, V. M. Farzaliev, M. A. Allokhverdiev, Russ. J. Appl. Chem. 79 (2006) 787

S. S. Bahekar, D. B. Shinde, Bioorg. Med. Chem. Lett. 14 (2004) 1733

S. Chitra, K. Pandiarajan, Tetrahedron Lett. 50 (2009) 2222

J. N. Liu, J. Li, L. Zhang, L. P. Song, M. Zhang, W. J. Cao, S. Z. Zhu, H. G. Deng, M. Shao, Tetrahedron Lett. 53 (2012) 2469

A. Kumar, R. A. Maurya, Tetrahedron Lett. 48 (2007) 4569

J. Lai, M. Sharma, S. Gupta, P. Parashar, P. Sahu, D. D. Agarwal, J. Mol. Catal., A: Chem. 352 (2012) 31

M. Litvić, I. Večenaj, Z. Mikuldaš Ladišić, M. Lovrić, V. Vinković, M. Filipan-Litvić, Tetrahedron 66 (2010) 3463

B. Ahmad, R. A. Khan, A. Habibullah, M. Keshai, Tetrahedron Lett. 50 (2009) 2889

A. Kamal, T. Krishnaji, M. A. Azhar, Catal. Commun. 8 (2007) 1929

Y. Zhang, B. Wang, X. Zhang, J. Huang, C. Liu, Molecules 20 (2015) 3811

P. Attri, R. Bhatia, J. Gaur, B. Arora, A. Gupta, N. Kumar, E. H. Choi, Arab. J. Chem. (2014), doi: http://dx.doi.org/10.1016/j.arabjc.2014.05.007

K. Aswin, S. S. Mansoor, K. Logaiya, P. N. Sudhan, R. N. Ahmed, J. Taibah Univ. Sci. 8 (2014) 236

A. Cano-Marquina, J. J. Tarín, A. Cano, Maturitas 75 (2013) 7

H. Qi, S. Li, Geriatr. Gerontol. Int. 14 (2014) 430

D. R. Lara, J. Alzheimer’s Dis. 20 (2010) S239

E. Poleszak, A. Szopa, E. Wyska, W. Kukuła-Koch, A. Serefko, S. Wośko, K. Bogatko, A. Wróbel, P. Wlaź, Pharmacol. Rep. 68 (2016) 56

A. Nehlig, J. L. Daval, G. Debry, Brain. Res. Rev. 17 (1992) 139

R. Mohebat, A. Yazdani-Elah, Chin. Chem. Lett. 28 (2017) 1340

A. Y. Elah Abadi, M. T. Maghsoodlou, R. Heydari, R. Mohebat, Res. Chem. Intermed. 42 (2016) 1227

M. T. Maghsoodlou, R. Heydari, M. Lashkari, F. Mohamadpour, Indian. J. Chem., Sect. B 56 (2017) 160

H. Bahrami, M. Tabrizchi, H. Farrokhpour, Chem. Phys. 415 (2013) 222.




DOI: https://doi.org/10.2298/JSC170712041M

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