Abstract
Preparation and application of novel and reusable magnetic nanoparticles with poly N,N-dimethylaniline-formaldehyde support as a heterogeneous basic catalyst have been described. The reported catalyst was characterized by Fourier transform infrared spectroscopy, scanning electron microscopy, X-ray diffraction patterns, transmission electron microscopy, energy dispersive X-ray spectroscopy, thermogravimetric analysis and vibrating sample magnetometry. The catalytic performance of this organic-inorganic hybrid nanomaterial has been studied for the green synthesis of 2-amino-3-cyanopyridine derivatives through one-pot four-component reactions. An eco-friendly method, short reaction time, high yield and easy work-up procedure are the advantages of this new methodology over earlier ones.
Similar content being viewed by others
References
V. Polshettiwar, R.S. Varma, Pure Appl. Chem. 80, 777 (2008)
J. Tang, L. Wang, Y. Yao, L. Zhang, W. Wang, Tetrahedron Lett. 52, 509 (2011)
N.M. Evdokimov, A.S. Kireev, A.A. Yakovenko, M.Y. Antipin, I.V. Magedov, A. Kornienko, J. Org. Chem. 72, 3443 (2007)
T. Šmejkal, B. Breit, Angew. Chem. 120, 317 (2008)
R. Makiura, S. Motoyama, Y. Umemura, H. Yamanaka, O. Sakata, H. Kitagawa, Nat. Mater. 9, 565 (2010)
D. Bora, B. Deb, A.L. Fuller, A.M. Slawin, J.D. Woollins, D.K. Dutta, Inorg. Chim. Acta 363, 1539 (2010)
N. De Rycke, F. Couty, O.R. David, Chem. Eur. J. 17, 12852 (2011)
L. Jayasinghe, C.P. Jayasooriya, N. Hara, Y. Fujimoto, Tetrahedron Lett. 44, 8769 (2003)
C. Temple Jr., G.A. Rener, W.R. Waud, P.E. Noker, J. Med. Chem. 35, 3686 (1992)
S.G. Konda, V. Khedkar, B. Dawane, J. Chem. Pharm. Res. 2, 187 (2010)
A.E.G. Hammam, N.A.A. El-hafeza, W.H. Midurab, M. Mikołajczyk, Z. Naturforsch. Pt. B 55, 417 (2000)
D.C. Mungra, M.P. Patel, R.G. Patel, Arkivoc 14, 64 (2009)
A.R. Gholap, K.S. Toti, F. Shirazi, R. Kumari, M.K. Bhat, M.V. Deshpande, K.V. Srinivasan, Bioorg. Med. Chem. Lett. 15, 6705 (2007)
T. Murata, M. Shimada, S. Sakakibara, T. Yoshino, T. Masuda, T. Shintani, H. Sato, Y. Koriyama, K. Fukushima, N. Nunami, Bioorg. Med. Chem. Lett. 14, 4019 (2004)
F. Zhang, Y. Zhao, L. Sun, L. Ding, Y. Gu, P. Gong, Eur. J. Med. Chem. 46, 3149 (2011)
J. Deng, T. Sanchez, L.Q. Al-Mawsawi, R. Dayam, R.A. Yunes, A. Garofalo, M.B. Bolger, N. Neamati, Bioorg. Med. Chem. Lett. 15, 4985 (2007)
T. Murata, M. Shimada, S. Sakakibara, T. Yoshino, H. Kadono, T. Masuda, M. Shimazaki, T. Shintani, K. Fuchikami, K. Sakai, Bioorg. Med. Chem. Lett. 13, 913 (2003)
A. Girgis, A. Kalmouch, H. Hosni, Amino Acids 26, 139 (2004)
M.A. Bodaghifard, M. Solimannejad, S. Asadbegi, S. Dolatabadifarahani, Res. Chem. Intermed. 42, 1165 (2015)
R. Galeeva, E. Rudometova, M.Y. Gavrilov, V. Kolla, M. Kon’shin, F.Y. Nazmetdinov, Pharm. Chem. J. 31, 89 (1997)
A. Sakurai, H. Midorikawa, Bull. Chem. Soc. Jpn 41, 430 (1968)
S. Kambe, K. Saito, A. Sakurai, H. Midorikawa, Synthesis 1980, 366 (1980)
A. Mobinikhaledi, S. Asadbegi, M.A. Bodaghifard, Synth. Commun. 19, 1605 (2016)
S. Kankala, R. Pagadala, S. Maddila, C.S. Vasam, S.B. Jonnalagadda, RSC Adv. 5, 105446 (2015)
B. Maleki, S. Sheikh, Org. Prep. Proced. Int. 47, 368 (2015)
M.M. Heravi, S.Y.S. Beheshtiha, M. Dehghani, N. Hosseintash, J. Iran. Chem. Soc. 12, 2075 (2015)
D. Khalili, Tetrahedron Lett. 57, 1721 (2016)
M. Álvarez-Pérez, J. Marco-Contelles, Arkivoc 2, 283 (2011)
F. Shi, S. Tu, F. Fang, T. Li, Arkivoc 1, 137 (2005)
T.R. Reddy, G.R. Reddy, L.S. Reddy, S. Jammula, Y. Lingappa, R. Kapavarapu, C.L.T. Meda, K.V. Parsa, M. Pal, Eur. J. Med. Chem. 48, 265 (2012)
R. Swathi, K. Sebastian, Resonance 13, 548 (2008)
S. Roy, K.K. Senapati, P. Phukan, Res. Chem. Intermed. 41, 5753 (2015)
W. Zhou, J. Yi, J. Lin, S. Fang, X. Peng, Res. Chem. Intermed. 43, 3651 (2017)
V. Polshettiwar, T. Asefa, G. Hutchings, Nanocatalysis: Synthesis and Applications (Wiley, New York, 2013)
J. Dobson, Drug Dev. Res. 67, 55 (2006)
Q.A. Pankhurst, J. Connolly, S.K. Jones, J. Dobson, J. Phys. D Appl. Phys. 36, R167 (2003)
M.M. Khodaei, A. Alizadeh, M. Haghipour, Res. Chem. Intermed. (2017). https://doi.org/10.1007/s11164-017-3008-2
S. Sun, H. Zeng, J. Am. Chem. Soc. 124, 8204 (2002)
M.A. Zolfigol, R. Ayazi-Nasrabadi, RSC Adv. 6, 69595 (2016)
B. Zakerinasab, M. Nasseri, H. Hassani, M. Samieadel, Res. Chem. Intermed. 42, 3169 (2016)
Y. Lu, Y. Yin, B.T. Mayers, Y. Xia, Nano Lett. 2, 183 (2002)
W. Wu, Q. He, C. Jiang, Nanoscale Res. Lett. 3, 397 (2008)
M. Butterworth, L. Illum, S. Davis, Colloid Surf. A 179, 93 (2001)
S. Santra, R. Tapec, N. Theodoropoulou, J. Dobson, A. Hebard, W. Tan, Langmuir 17, 2900 (2001)
M. Pramanik, A. Bhaumik, ACS Appl. Mater. Interfaces. 6, 933 (2014)
M.A. Bodaghifard, A. Mobinikhaledi, S. Asadbegi, Appl. Organomet. Chem. 31, e3557 (2016)
M.A. Bodaghifard, S. Asadbegi, Z. Bahrami, J. Iran. Chem. Soc. 14, 365 (2016)
M.A. Bodaghifard, Z. Faraki, A.R. Karimi, Curr. Org. Chem. 20, 1648 (2016)
G. Feng, D. Hu, L. Yang, Y. Cui, X.-A. Cui, H. Li, Sep. Purif. Technol. 74, 253 (2010)
K. Petcharoen, A. Sirivat, Mater. Sci. Eng., B 177, 421 (2012)
Y. Wan, R. Yuan, F.-R. Zhang, L.-L. Pang, R. Ma, C.-H. Yue, W. Lin, W. Yin, R.-C. Bo, H. Wu, Synth. Commun. 41, 2997 (2011)
O. El-Salam, D. Ella, N. Ismail, M. Abdullah, Pharmazie 64, 147 (2009)
R. Pagadala, S. Maddila, S. Jonnalagadda, J. Heterocycl. Chem. 52, 1226 (2015)
R. Khalifeh, M. Ghamari, J. Braz. Chem. Soc. 27, 759 (2016)
S. Khaksar, M. Yaghoobi, J. Fluor. Chem. 142, 41 (2012)
Q. Wu, Y. Zhang, S. Cui, Org. Lett. 16, 1350 (2014)
M.A. Zolfigol, M. Kiafar, M. Yarie, A.A. Taherpour, M. Saeidi-Rad, RSC Adv. 6, 50100 (2016)
R. Pagadala, S. Maddila, V. Moodley, W.E. van Zyl, S.B. Jonnalagadda, Tetrahedron Lett. 55, 4006 (2014)
K. Can, M. Ozmen, M. Ersoz, Colloid Surf. B 71, 154 (2009)
W. Stöber, A. Fink, E. Bohn, J. Colloid Interface Sci. 26, 62 (1968)
T. Zeng, L. Yang, R. Hudson, G. Song, A.R. Moores, C.-J. Li, Org. Lett. 13, 442 (2010)
Acknowledgements
We gratefully acknowledge the financial support of this work by the research council of Arak University.
Author information
Authors and Affiliations
Corresponding author
Electronic supplementary material
Below is the link to the electronic supplementary material.
Rights and permissions
About this article
Cite this article
Asadbegi, S., Bodaghifard, M.A. & Mobinikhaledi, A. Poly N,N-dimethylaniline-formaldehyde supported on silica-coated magnetic nanoparticles: a novel and retrievable catalyst for green synthesis of 2-amino-3-cyanopyridines. Res Chem Intermed 46, 1629–1643 (2020). https://doi.org/10.1007/s11164-017-3200-4
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11164-017-3200-4