Fatemeh MIRHASHEMI, Mohammad Ali AMROLLAHI

Host/guest inclusion system of surfactants with -cyclodextrin as a viable catalyst for one-pot synthesis of mono - and bis (indolyl)methylmalononitriles in H 2 O

In this study, encapsulation processes of cetyltrimethylammonium bromide (CTAB) or sodium dodecyl sulfate (SDS) monomers into the cavity of ββ\beta -cyclodextrin (ββ\beta -CD) were applied to synthesize mono - and bis (indolyl)methylmalononitrile derivatives by a one-pot three-component reaction of an aldehyde, malononitrile, and indole in an aqueous solution. These two inclusion complexes proved to be superior to CTAB or SDS individually, as cationic or anionic surfactants, respectively, for accessing high yields of pure products within shorter reaction times. In addition, simple isolation of products and mild reaction conditions are the other advantages of this green procedure.

Keywords:

Conductance ; -cyclodextrin, encapsulation inclusion complexes, surfactants,

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Manabe, K.; Mori, Y.; Wakabayashi, T.; Nagayama, S.; Kobayashi, S. J. Am. Chem. Soc . 2000 , 122 , 7202-7207.
Stepankova, V.; Damborsky, J.; Chaloupkova, R. Biotechnol. J . 2013 , 8 , 719-729.
Galan, M. C.; Tran, A. T.; Whitaker, S. Chem. Commun . 2010 , 46 , 2106-2108.
Megens, R. P.; Roelfes, G. Org. Biomol. Chem . 2010 , 8 , 1387-1393.
Talbi, B.; Haquette, P.; A. Martel, A.; Montigny, F. D.; Fosse, C.; Cordier, S.; Roisnel, T.; J. G. Salmain, J. G. Dalton Trans. 2010 , 39 , 5605-5607.
Firouzabadi, H.; Iranpoor, N.; Jafari, A. A. Tetrahedron Lett . 2005 , 46 , 2683-2686.
Satoh, K.; Kamigaito, M.; Sawamoto, M. Macromolecules 2000 , 33 , 5836-5840.
Rebacz, N. A.; Savage P. E. Ind. Eng. Chem. Res. 2010 , 49 , 535-540.
Corma, A.; Domine, M. E.; Valencia, S . J. Catal. 2003 , 215 , 294-304.
Trembleau, L.; Rebek, J. Chem. Commun . 2004 , 1 , 58-59.
Klein, R.; Touraud, D.; Kunz, W. Green Chem . 2008 , 10 , 433-435 :
Jafari A. A.; Ghadami, M. Chem. Lett. 2016 , 14 , 215-221.
Ye, Y.; Ding, Q.; Wu, J. Tetrahedron 2008 , 64 , 1378-1382.
Firouzabadi, H.; Iranpoor N.; Khoshnood, A. J. Mol. Catal. A Chem . 2007 , 274 , 109-115.
Manabe, K.; Iimura, S.; Sun, X. M.; Kobayashi, S. J. Am. Chem. Soc . 2002 , 124 , 11971-11978.
Manabe, K.; Kobayashi, S. Org. Lett. 1999 , 1 , 1965-1967.
Gargm, R. Supramolecular Chemistry of Host-Guest Inclusion Complexes ; GRIN Verlag: Dordrecht, Netherlands, 2013.
Atwood, J. L. Molecular Recognition and Inclusion ; Kluwer Academic Publishers: Norderstedt, Germany, 1998.
Szejtli, J. Chem. Rev. 19981 , 98 , 1743-1754.
Zhang, J.; Ma, P. X. Adv. Drug. Deliv . Rev. 2013 , 65 , 1215-1233.
Tanford, C. The Hydrophobic Effect ; Wiley: New York, NY, USA, 1973.
Rosen, M. J. Surfactants and Interfacial Phenomena ; Wiley: New York, NY, USA, 2004.
Tadros, T. F. Applied Surfactants, Principles and Applications ; Wiley-VCH Verlag, Weinheim, Germany, 2005.
Svenson, S. Curr. Opin. Colloid Interface Sci . 2004 , 9 , 201-212.
Guo, T.; Huang, F.; Yu, L.; Yu, Z. Tetrahedron Lett. 2015 , 56 , 296-302.
Rahimi, S.; Amrollahi, M. A.; Kheilkordi, Z. C. R. Chim . 2015 , 18 , 558-563.
Li, J. T.; Lin, Z. P. Ultrason. Sonochem. 2008 , 15 , 265-268.
Rajesh, U. C.; Kholiya, R.; Thakur, A.; Rawat, D. S. Tetrahedron Lett . 2015 , 56 , 1790-1793.
Omidi M.; Amrollahi, M. A.; C. R. Chim . 2016 , 20 , 1-5.
Chandrasekhar, S.; Patro, V.; Reddy, G. P. K.; Grée, R. Tetrahedron Lett. 2012 , 53 , 6223-6225.
Wang, L.; Huang, M.; Zhu, X.; Wan, Y . Appl.Catal A-Gen. 2013 , 454 , 160-163.
Jari, T.; Amrollahi, M. A.; Kheilkordi, Z. Heterocycl. Commun . 2015 , 21 , 89-92.