Abstract
In this study, we present a straightforward, efficient and convenient approach for the synthesis of medicinally important 1,4-dihydrobenzo[4,5] imidazo [1,2-a]pyrimidine-3-carboxylates via three-component reactions of aldehydes, 1H-benzo[d]imidazol-2-amine and active methylene compounds in the presence of di-n-butyl ammonium chlorosulfonate ionic liquids (DBA IL) under ultrasound irradiation. This process develops the synthetic potential of ultrasound irradiation with DBA IL combination and presents much compensation, such as outstanding product yields, reusable catalyst, less reaction periods, gainful cost, easy work-up/purification and environmentally benign reaction conditions.
Graphical Abstract
The attractive features of this methodology are simple procedure, green reaction, reusability and high efficiency of the catalyst, and easy workability.
Similar content being viewed by others
References
P. Molina, M.J. Vilaplana, Synthesis 1197 (1994)
A. Deiters, S.F. Martin, Chem. Rev. 104, 2199 (2004)
X.F. Wu, H. Neumann, M. Beller, Chem. Rev. 113, 1 (2013)
A.V. Gulevich, A.S. Dudnik, N. Chernyak, V. Gevorgyan, Chem. Rev. 113, 3084 (2013)
S. Hameed, T. Akhtar, Curr. Org. Chem. 15, 694 (2011)
S. Sadjadi, M.M. Heravi, Tetrahedron 67, 2707 (2011)
R. Alajarin, J. Alvarez-Builla, J.J. Vaquero, C. Sunkel, M. Fau de Casa-Junna, P.R. Statkow, J. Sanz-Aparicio, Tetrahedron Asymmetry 4, 617 (1993)
F. Bossert, W. Vater, Med. Res. Rev. 9, 291 (1989)
M. Cheung, P.A. Harris, M. Hasegawa, S. Ida, K. Kano, N. Nishigaki, H. Sato, J.M. Veal, Y. Washio, R.I. West, WO. Pat., 2002044156 (2002)
J.J. Nunes, X.T. Zhu, M. Ermann, C. Ghiron, D.N. Johnston, C.G.P. Saluste, WO. Pat., 2005021551 (2005)
J.J. Nunes, X.T. Zhu, P. Amouzegh, C. Ghiron, D.N. Johnston, E.C. Power, WO. Pat., 2005009443 (2005)
A.A.M. Abdel-Hafez, Arch. Pharm. Res. 30, 678 (2007)
J.P. Whitten, M. Schwaebe, WO. Pat., 2008060693 (2008)
M.W. Martin, J. Newcomb, J.J. Nunes, C. Boucher, L. Chai, L.F. Epstein, T. Faust, S. Flores, P. Gallant, A. Gore, Y. Gu, F. Hsieh, X. Huang, J.L.S. Kim, S. Middleton, K. Morgenstern, A. Oliveira-dos-Santos, V.F. Patel, D. Powers, P. Rose, Y. Tudor, S.M. Turci, A.A. Welcher, D. Zack, H.L. Zhao, L. Zhu, X.T. Zhu, C. Ghiron, M. Ermann, D. Johnston, C.G.P. Saluste, J. Med. Chem. 51, 1637 (2008)
N. Zanatta, S.S. Amaral, A. Esteves-Souza, A. Echevarria, P.B. Brondani, D.C. Flores, H.G. Bonacorso, A.F.C. Flores, M.A.P. Martins, Synthesis 14, 2305 (2006)
B.B. Snider, Z. Shi, J. Org. Chem. 58, 3828 (1993)
L.E. Overman, M.H. Rabinowitz, P.A. Renhowe, J. Am. Chem. Soc. 117, 2657 (1995)
A. Shaabani, A. Rahmati, S. Naderi, Bioorg. Med. Chem. Lett. 15, 5553 (2005)
J. Liu, M. Lei, L. Hu, Green Chem. 14, 840 (2012)
Y. Chang-Shenga, L. Songa, W. Cui-Huaa, Y. Chen-Xiaa, S. Qing-Qinga, T. Shu-Jiang, Chin. J. Chem. 26, 2107 (2008)
L. Wu, F. Yan, C. Yang, Bull. Chem. Soc. Ethiop. 24, 417 (2010)
A. Shaabani, A. Rahmati, A.H. Rezayan, M. Darvishi, Z. Badri, A. Sarvari, QSAR Comb. Sci. 26, 973 (2007)
C. Yao, S. Lei, C. Wang, T. Li, C. Yu, X. Wang, S. Tu, J. Heterocycl. Chem. 47, 26 (2010)
S. Tu, Q. Shao, D. Zhou, L. Cao, F. Shi, C. Li, J. Heterocycl. Chem. 44, 1401 (2007)
S. Ya-Li, D. Yun-Fang, W. Fan, Y. Tao, Y. Geng-Liang, Ultrason. Sonochem. 22, 119 (2015)
L. Wang, A. Keyume, J. Feng, Ultrason. Sonochem. 22, 113 (2015)
G. Javad Safaei, A. Zeinab, Ultrason. Sonochem. 22, 365 (2015)
R. Suman, M. Priyabrata, M. Chhanda, Ultrason. Sonochem. 22, 22 (2015)
A. Yinga, L. Wanga, F. Qiua, H. Hua, J. Yang, C.R. Chimie 18, 223 (2015)
Md Nasim Khan, S. Karamthulla, L.H. Choudhury, Md Serajul Haque Faizib, RSC Adv. 5, 22168 (2015)
K. Azizi, M. Karimi, H. Reza Shaterianb, A. Heydari, RSC Adv. 4, 42220 (2014)
B. Thirupathaiahy, M. Veeranarayana Reddy, Y. Tae Jeong, Tetrahedron 71, 2168 (2015)
K. Bheru Singh, M. Singh, New J. Chem. 38, 4290 (2014)
G.L. Balaji, K. Rajesh, M. Venkatesh, S. Sarveswari, V. Vijayakumar, RSC Adv. 4, 39 (2014)
M. Veeranarayana Reddy, K. Taek Lim, J. Tae Kim, Y. Tae Jeong, J. Chem. Res. 7, 398 (2012)
K. Erfurt, I. Wandzik, K. Walczak, K. Matuszek, A. Chrobok, Green Chem. 16, 3508 (2014)
V. Fuente, N. Fleury-Brégeot, S. Castillón, C. Claver, Green Chem. 14, 2715 (2012)
D. Arup Kumar, P. Gogoia, R. Borah, RSC Adv. 4, 41287 (2014)
Q. Yan, H. Zang, C. Wu, J. Feng, M. Li, M. Zhang, L. Wang, B. Cheng, J. Mol. Liq. 204, 156 (2015)
J. Isaad, RSC Adv. 4, 49333 (2014)
A. Khalafi-Nezhad, M. Somayeh, RSC Adv. 4, 13782 (2014)
H. Zhou, J. Song, X. Kang, J. Hu, Y. Yang, H. Fan, Q. Menga, B. Han, RSC Adv. 5, 15267 (2015)
K. Ali Reza, Z. Dalirnasab, M. Karimi, Synthesis 46, 917 (2014)
P. Sharma, M. Gupta, Green Chem. 17, 1100 (2015)
M. Veeranarayana Reddy, K. Reddi Mohan Naidu, L. Sang Dong, Y.T. Jeong, Catal. Commun. 61, 102 (2015)
G. Chatel, D.R. MacFarlane, Chem. Soc. Rev. 43, 8132 (2014)
S. Marullo, F.D. Anna, C. Rizzo, R. Noto, Ultrason. Sonochem. 23, 317 (2015)
M. Veeranarayana Reddy, G. Chandra Sekhar Reddy, K. Reddi Mohan Naidu, Y. Tae Jeong, RSC Adv. 5, 35267 (2015)
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
Reddy, M.V., Reddy, A.V.S. & Jeong, Y.T. Di-n-butyl ammonium chlorosulfonate ionic liquids as an efficient and recyclable catalyst for the synthesis of 1,4-dihydrobenzo[4,5]imidazo[1,2-a]pyrimidine-3-carboxylates under solvent-free ultrasound irradiation. Res Chem Intermed 42, 4893–4906 (2016). https://doi.org/10.1007/s11164-015-2328-3
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11164-015-2328-3