Generic placeholder image

Letters in Organic Chemistry

Editor-in-Chief

ISSN (Print): 1570-1786
ISSN (Online): 1875-6255

Letter Article

Ecofriendly Synthesis of Formamidine Derivatives Catalyzed by Al-MCM- 41 Mesoporous Materials

Author(s): Datoussaid Yazid*, Ali-Dahmane Tewfik, Mehiaoui Nawel, Lamia Brahmi, Kibou Zahira, Hamacha Rachida and Choukchou-Braham Noureddine

Volume 19, Issue 5, 2022

Published on: 18 February, 2021

Page: [347 - 352] Pages: 6

DOI: 10.2174/1570178618666210218212300

Price: $65

Abstract

Formamidine derivatives have been synthesized in excellent yields at room temperature from primary amine and N,N-dimethylformamide dimethylacetal (DMF-DMA) in the presence of a catalytic amount of Al-MCM-41 synthesized from natural bentonite as silica and aluminum source. The advantages of this method are the use of a cheap, stable, non-toxic, and readily available catalyst, easy work-up, improved yields, and solvent-free conditions.

Keywords: Formamidine, DMF-DMA, Al-MCM-41, mesoporous materials, heterogeneous catalysis, formamidine derivatives.

Graphical Abstract
[1]
Erian, A.W.; Sherif, S.M.; Alassar, A-Z.A.; Elkholy, Y.M. Tetrahedron, 1994, 50, 1877-1884.
[http://dx.doi.org/10.1016/S0040-4020(01)80859-0]
[2]
Meyers, A.; Marra, J.M. Tetrahedron Lett., 1985, 26, 5863-5866.
[http://dx.doi.org/10.1016/S0040-4039(00)98247-9]
[3]
Belhadj, F.; Kibou, Z.; Cheikh, N.; Choukchou-Braham, N.; Villemin, D. Tetrahedron Lett., 2015, 56, 5999-6002.
[http://dx.doi.org/10.1016/j.tetlet.2015.09.042]
[4]
Jalani, H.B.; Pandya, A.N.; Pandya, D.H.; Sharma, J.A.; Sudarsanam, V.; Vasu, K.K. Tetrahedron Lett., 2012, 53, 4062-4064.
[http://dx.doi.org/10.1016/j.tetlet.2012.05.104]
[5]
Furth, H.P.S.; Reitman, M.S.; Cook, A.F. Tetrahedron Lett., 1997, 38, 5403-5406.
[http://dx.doi.org/10.1016/S0040-4039(97)01200-8]
[6]
Lüth, A.; Löwe, W. Eur. J. Med. Chem., 2008, 43(7), 1478-1488.
[http://dx.doi.org/10.1016/j.ejmech.2007.09.018] [PMID: 17981366]
[7]
Zhang, M.; Jiang, L.; Tao, J.; Pan, Z.; He, M.; Su, D.; He, G.; Jiang, Q. Bioorg. Med. Chem., 2019, 27(11), 2268-2279.
[http://dx.doi.org/10.1016/j.bmc.2019.04.022] [PMID: 31014565]
[8]
Toste, D.; McNulty, J.; Still, I.W. Synth. Commun., 1994, 24, 1617-1624.
[http://dx.doi.org/10.1080/00397919408010163]
[9]
Vincent, S.; Mons, S.; Lebeau, L.; Mioskowski, C. Tetrahedron Lett., 1997, 38, 7527-7530.
[http://dx.doi.org/10.1016/S0040-4039(97)10023-5]
[10]
Meesala, R.; Arshad, A.S.M.; Mordi, M.N.; Mansor, S.M. Tetrahedron Lett., 2014, 55, 7023-7025.
[http://dx.doi.org/10.1016/j.tetlet.2014.10.123]
[11]
Dar, B.A.; Ahmad, S.N.; Wagay, M.A.; Hussain, A.; Ahmad, N.; Bhat, K.A.; Khuroo, M.A.; Sharma, M.; Singh, B. Tetrahedron Lett., 2013, 54, 4880-4884.
[http://dx.doi.org/10.1016/j.tetlet.2013.06.131]
[12]
Han, Y.; Cai, L. Tetrahedron Lett., 1997, 38, 5423-5426.
[http://dx.doi.org/10.1016/S0040-4039(97)01206-9]
[13]
Mekhalfia, A.; Mutter, R.; Heal, W.; Chen, B. Tetrahedron, 2006, 62, 5617-5625.
[http://dx.doi.org/10.1016/j.tet.2006.03.099]
[14]
Abu‐Shanab, F.A.; Sherif, S.M.; Mousa, S.A. J. Heterocycl. Chem., 2009, 46, 801-827.
[http://dx.doi.org/10.1002/jhet.69]
[15]
Patil, P. S.; Chavan, S. M.; Toche, R. B.; Bhole, A. D.; Patil, V. M.; Aware, P. B. IOSR- JAC., 2017, 10, 96-100.
[16]
Chandregowda, V.; Venkateswara Rao, G.; Chandrasekara Reddy, G. Org. Process Res. Dev., 2007, 11, 813-816.
[http://dx.doi.org/10.1021/op700054p]
[17]
Sartori, G.; Ballini, R.; Bigi, F.; Bosica, G.; Maggi, R.; Righi, P. Chem. Rev., 2004, 104(1), 199-250.
[http://dx.doi.org/10.1021/cr0200769] [PMID: 14719975]
[18]
Berrichi, A.; Bachir, R.; Benabdallah, M.; Choukchou-Braham, N. Tetrahedron Lett., 2015, 56, 1302-1306.
[http://dx.doi.org/10.1016/j.tetlet.2015.01.132]
[19]
Berrichi, A.; Bachir, R.; Bedrane, S.; Choukchou-Braham, N.; Belkacemi, K. Res. Chem. Intermed., 2019, 45, 3481-3495.
[http://dx.doi.org/10.1007/s11164-019-03803-6]
[20]
Ferouani, G.; Ameur, N.; Bachir, R. Res. Chem. Intermed., 2020, 46, 1373-1387.
[http://dx.doi.org/10.1007/s11164-019-04039-0]
[21]
Brahmi, L.; Ali-Dahmane, T.; Hamacha, R.; Hacini, S. J. Mol. Catal. Chem., 2016, 423, 31-40.
[http://dx.doi.org/10.1016/j.molcata.2016.06.004]
[22]
Chen, D.; Yang, Y.; Zhang, X.; Wang, X.; Xu, Y.; Qian, G. Int. J. Hydrogen Energy, 2019, 44, 18123-18133.
[http://dx.doi.org/10.1016/j.ijhydene.2019.03.106]
[23]
Jermy, R.; Arumugam, P. Appl. Catal. A Gen., 2005, 288, 25-33.
[http://dx.doi.org/10.1016/j.apcata.2005.03.047]
[24]
Nouali, F.; Kibou, Z.; Boukoussa, B.; Choukchou-Braham, N.; Bengueddach, A.; Villemin, D.; Hamacha, R. Res. Chem. Intermed., 2020, 46, 3179-3191.
[http://dx.doi.org/10.1007/s11164-020-04144-5]
[25]
Selvaraj, M.; Pandurangan, A.; Seshadri, K.; Sinha, P.; Lal, K. Appl. Catal. A Gen., 2003, 242, 347-364.
[http://dx.doi.org/10.1016/S0926-860X(02)00527-6]
[26]
Boukoussa, B.; Kibou, Z.; Abid, Z.; Ouargli, R.; Choukchou-Braham, N.; Villemin, D.; Bengueddach, A.; Hamacha, R. Chem. Pap., 2018, 72, 289-299.
[http://dx.doi.org/10.1007/s11696-017-0279-4]
[27]
Villemin, D.; Belhadj, Z.; Cheikh, N.; Choukchou-Braham, N.; Bar, N.; Lohier, J-F. Tetrahedron Lett., 2013, 54, 1664-1668.
[http://dx.doi.org/10.1016/j.tetlet.2013.01.021]
[28]
Kibou, Z.; Cheikh, N.; Villemin, D.; Choukchou-Braham, N.; Mostefa-Kara, B.; Benabdallah, M. Int. J. Org. Chem. (Irvine), 2011, 1, 242-249.
[http://dx.doi.org/10.4236/ijoc.2011.14035]
[29]
Medjdoub, A.; Belhadj, F.; Merzouk, A.S.; Hamed, Y.B.; Kibou, Z.; Choukchou-Braham, N.; Merzouk, H. Chem. Pap., 2020, 74, 903-913.
[http://dx.doi.org/10.1007/s11696-019-00924-5]
[30]
Ali-Dahmane, T.; Adjdir, M.; Hamacha, R.; Villieras, F.; Bengueddach, A.; Weidler, P.G. C. R. Chim., 2014, 17, 1-6.
[http://dx.doi.org/10.1016/j.crci.2012.12.017]
[31]
Ali-Dahmane, T.; Hamacha, R.; Hacini, S.; Bengueddach, A. Bull. Chem. React. Eng. Catal., 2019, 14, 358-368.
[http://dx.doi.org/10.9767/bcrec.14.2.3367.358-368]

Rights & Permissions Print Cite
© 2024 Bentham Science Publishers | Privacy Policy