Abstract
An environmentally benign and efficient method has been developed for the synthesis of a series of 2H-indazolo[2,1-b]phthalazine-triones derivatives with β-cyclodextrine-SO3H as a recyclable catalyst by simply combining of various aldehydes with cyclic 1,3-diketones and phthalhydrazide under solvent free condition. The advantageous features of this methodology are high atom-economy, operational simplicity, shorter reaction time, convergence, and facile automation.
Graphical Abstract
A greener, efficient, and expeditious method has been developed for the synthesis of 2H-indazolo [2,1-b] phthalazine-triones derivatives with β-cyclodextrine-SO3H as a recyclable catalyst for the first time.
Similar content being viewed by others
References
V.P. Litvinov, Russ. Chem. Rev. 72, 69 (2003)
W.B. Chen, Z.-J. Wu, Q.-L. Pei, L.-F. Cun, X.-M. Zhang, W.-C. Yuan, Org. Lett. 12, 3132 (2010)
S. Grasso, G. DeSarro, N. Micale, M. Zappala, G. Puia, M. Baraldi, C. Demicheli, J. Med. Chem. 43, 2851 (2000)
J.S. Kim, H.K. Rhee, H.J. Park, S.K. Lee, C.O. Lee, H.Y. Park Choo, Bioorg. Med. Chem. 16, 4545 (2008)
S.S. El-Saka, A.H. Soliman, A.M. Imam, Afinidad J 66, 167 (2009)
L. Zhang, L.P. Guan, X.Y. Sun, C.X. Wei, K.Y. Chai, Z.S. Quan, Chem. Biol. Drug Des. 73, 313 (2009)
H. Wu, X.M. Chen, Y. Wan, H.Q. Xin, H.H. Xu, R. Ma, C.H. Yue, L.L. Pang, Lett. Org. Chem. 6, 219 (2009)
E.L. Piatnitski, M.A.J. Duncton, A.S. Kiselyov, R. Katoch-Rouse, D. Sherman, D.L. Milligan, C. Balagtas, W.C. Wong, J. Kawakami, J.F. Doody, Bioorg. Med. Chem. Lett. 15, 4696 (2005)
J. Sinkkonen, V. Ovcharenko, K.N. Zelenin, I.P. Bezhan, B.A. Chakchir, F. Al-Assar, K. Pihlaja, Eur. J. Org. Chem. 12, 2046 (2002)
M. Sayyafi, M. Sayyedhamzeh, H.R. Khavasi, A. Bazgir, Tetrahedron 64, 2375 (2008)
R. Ghorbani-Vaghei, R. Karimi-Nami, Z. Toghraei-Semiromi, M. Amiri, M.M. Ghavidel, Tetrahedron 67, 1930 (2011)
G. Shukla, R.K. Verma, G.K. Verma, M.S. Singh, Tetrahedron Lett. 52, 7195 (2011)
M. Kidwai, R. Chauhan, A. Jahan, Chin. Sci. Bull. 57, 2273 (2012)
H.J. Wang, X.N. Zhang, Z.H. Zhang, Monatsh. Chem. 141, 425 (2010)
E. Mosaddegh, A. Hassankhani, Tetrahedron Lett. 52, 488 (2011)
A. Corma, H. Garcia, Catal. Today 38, 257 (1997)
M.V. Reddy, G.C.S. Reddy, Y.T. Jeong, Tetrahedron 68, 6820 (2012)
H.R. Shaterian, M. Ghashang, M. Feyzi, Appl. Catal. A 345, 128 (2008)
G. Sabitha, C. Srinivas, A. Raghavendar, J.S. Yadav, Helv. Chim. Acta 93, 1375 (2010)
T. Khan, Z.N. Siddiqui, New J. Chem. 38, 4847 (2014)
G.J. Hernandez, E. Juaristi, J. Org. Chem. 75, 7107 (2010)
M.S. Singh, S. Chowdhury, RSC Adv. 2, 4547 (2012)
J. Wu, X. Du, J. Ma, Y. Zhang, Q. Shi, L. Luo, B. Song, S. Yang, D. Hu, Green Chem. 16, 3210 (2014)
A.B. Atar, Y.S. Jeong, Y.T. Jeong, Tetrahedron 70, 5207 (2014)
A.B. Atar, Y.T. Jeong, Tetrahedron Lett. 54, 1302 (2013)
A.B. Atar, Y.T. Jeong, Tetrahedron Lett. 54, 5624 (2013)
A.B. Atar, J.S. Kim, K.T. Lim, Y.T. Jeong, New J. Chem. 39, 396 (2015)
A.B. Atar, J.T. Kim, K.T. Lim, Y.T. Jeong, Synth. Commun. 44, 2679 (2014)
S. Asghari, M. Tajbakhsh, B.J. Kenari, S. Khaksar, Chin. Chem. Lett. 22, 127 (2011)
Acknowledgments
This research work was supported by the BK 21 plus program.
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
Atar, A.B., Lee, S.D., Cho, B.G. et al. β-Cyclodextrine-SO3H: the most efficient catalyst for one-pot synthesis of 2H-indazolo[2,1-b]phthalazine-triones under solvent-free conditions. Res Chem Intermed 42, 1707–1728 (2016). https://doi.org/10.1007/s11164-015-2113-3
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11164-015-2113-3