Abstract
Efficient and green reactions of different aromatic aldehydes, 3-amino-1-phenyl-1H-pyrazol-5(4H)-one, and substituted 3-aminopyrazoles for the synthesis of pyrazolo[3,4-b:4′,3′-e]pyridin-3(2H)-one derivatives have been reported through deamination cyclization reactions. This is a new route for the generation of pyrazolo[3,4-b:4′,3′-e]pyridin-3(2H)-one compounds. According to the reported literature, these kinds of compounds have important optical properties, and have potential application prospects. Other advantages of this process are simple operation, easy separation, and a wide range of substrates. Best of all, this method possesses an environmentally benign procedure.
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P.K. Chinthakindi, H.G. Kruger, T. Govender, T. Naicker, P.I. Arvidsson, J. Org. Chem. 81, 2618 (2016)
L. Yang, T. Dong, H.M. Revankar, C.P. Zhang, Green Chem. 19, 3951 (2017)
P. Norcott, S.P. McErlean, Org. Biomol. Chem. 14, 1288 (2016)
B. Li, P.H. Dixneuf, Chem. Soc. Rev. 42, 5744 (2013)
P. Czerwiński, M. Michalak, J. Org. Chem. 82, 7980 (2017)
J. Xu, L. Qiao, J. Shen, K. Chai, P. Zhang, Org. Lett. 19, 5661 (2017)
H. de Mello, A. Echevarria, A.M. Bernardino, M. Canto-Cavalheiro, L.L. Leon, J. Med. Chem. 47, 5427 (2004)
T.J. Tucker, J.T. Sisko, R.M. Tynebor, T.M. Williams, P.J. Felock, J.A. Flynn, M.T. Lai, Y. Liang, G. McGaughey, M. Liu, M. Miller, G. Moyer, V. Munshi, R. Perlow-Poehnelt, S. Prasad, J.C. Reid, R. Sanchez, M. Torrent, J.P. Vacca, B.L. Wan, Y. Yan, J. Med. Chem. 51, 6503 (2008)
H. Ochiai, A. Ishida, T. Ohtani, K. Kusumi, K. Kishikawa, S. Yamamoto, H. Takeda, T. Obata, H. Makai, M. Toda, Bioorg. Med. Chem. 12, 4089 (2004)
A. Cappelli, C. Nannicini, A. Gallelli, G. Giuliani, S. Valenti, G.P. Mohr, M. Anzini, L. Mennuni, F. Ferrari, G. Caselli, A. Giordani, W. Pereis, F. Makovec, G. Giorgi, S. Vomero, J. Med. Chem. 51, 2137 (2008)
L. Revesz, E. Blum, F.E. Di Padova, T. Buhl, R. Feifel, H. Gram, P. Hiestand, U. Manning, U. Neumann, G. Rucklin, Bioorg. Med. Chem. Lett. 16, 262 (2006)
F. Manetti, S. Schenone, F. Bondavalli, C. Brullo, O. Bruno, A. Ranise, L. Mosti, G. Menozzi, P. Fossa, M.L. Trincavelli, C. Martini, A. Martinelli, C. Tintori, M. Botta, J. Med. Chem. 48, 7172 (2005)
T. Tuccinardi, S. Schenone, F. Bondavalli, C. Brullo, O. Bruno, L. Mosti, A.T. Zizzari, C. Tintori, F. Manetti, C. Oiampi, M.L. Trincavelli, C. Martini, A. Martinelli, M. Botta, ChemMedChem 3, 898 (2008)
G.M. Shutske, J.E. Roehr, J. Heterocyclic Chem. 34, 789 (1997)
B.R. Henke, C.J. Aquino, L.S. Birkemo, D.K. Croom, R.W. Dougherty, G.N. Ervin, M.K. Grizzle, G.C. Hirst, M.K. James, M.F. Johnson, K.L. Queen, R.G. Sherrill, E.E. Sugg, E.M. Suh, J.W. Szewczyk, R.J. Unwalla, J. Yingling, T.M. Willson, J. Med. Chem. 40, 2706 (1997)
A. Straub, J. Benet-Buckholtz, R. Frode, A. Kern, C. Kohlsdorfer, P. Schmitt, T. Schwarz, H.M. Siefert, J.P. Stasch, Bioorg. Med. Chem. 10, 1711 (2002)
Y.S. Sanghvi, S.B. Larson, R.C. Willis, R.K. Robins, G.R. Revankar, J. Med. Chem. 32, 945 (1989)
C.H. Chuen, Y.T. Tao, Appl. Phys. Lett. 81, 4409 (2002)
K. Rechthaler, R. Schamschule, A.B.J. Parusel, K. Rotkiewicz, D. Piorun, G. Kohler, Acta Phys. Pol., A 95, 321 (1999)
Z. He, G. Milburn, A. Danel, A. Puchala, P. Tomasik, D. Rasala. J. Mater. Chem. 7, 2323 (1997)
A.B.J. Parusel, R. Schamschule, D. Piorun, K. Rechthaler, A. Puchała, D. Rasała, K. Rotkiewicz, G. Kohler, J. Mol. Struct. (TEOCHEM) 419, 63 (1997)
K.C. Joshi, K. Dubey, A. Dandia, Pharmazie 36, 336 (1981)
J. Quiroga, J. Portilla, B. Insuasty, R. Abonia, M. Nogueras, M. Sortino, S. Zacchino, J. Heterocycl. Chem. 42, 61 (2005)
N.J. Green, J. Xiang, J. Chen, L. Chen, A.M. Davies, D. Erbe, S. Tam, J.F. Tobin, Bioorg. Med. Chem. 11, 2991 (2003)
P. Acosta, B. Insuasty, A. Ortiz, R. Abonia, M. Sortino, S.A. Zacchino, J. Quiroga, Arab. J. Chem. 9, 481 (2016)
R. Ghahremanzadeh, M. Sayyafi, S. Ahadi, A. Bazgir, J. Comb. Chem. 11, 393 (2009)
B. Jiang, W. Fan, M.Y. Sun, Q. Ye, S.L. Wang, S.J. Tu, G. Li, J. Org. Chem. 79, 5258 (2014)
Z. Chen, Y. Shi, Q. Shen, H. Xu, F. Zhang, Tetrahedron Lett. 56, 4749 (2015)
K. Karnakar, S.N. Murthy, K. Ramesh, G. Satish, J.B. Nanubolu, Y.V.D. Nageswar, Tetrahedron Lett. 53, 2897 (2012)
X. Zhang, D. Li, X. Fan, X. Wang, X. Li, Mol. Divers. 14, 159 (2010)
A. Rahmati, T. Kenarkoohi, H.R. Khavasi, ACS Comb. Sci. 14, 657 (2012)
Z. Huang, Y. Hu, Y. Zhou, D.Q. Shi, ACS Comb. Sci. 13, 45 (2011)
S.S. Xu, Z.S. Wang, X.L. Li, L.C. Rong, S.J. Tu, Tetrahedron 72, 5754 (2016)
Z.S. Wang, L.L. Gao, Z.Y. Xu, Z. Ling, Y.Q. Qin, L.C. Rong, S.J. Tu, Tetrahedron 73, 385 (2017)
Acknowledgements
We are grateful to the National Natural Science Foundation of China (NSFC) (51174201, 21571087), the Open Foundation of Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials (K201312), the Major Projects of Natural Science Research in Jiangsu Province (15KJA150004), and the Priority Academic Program Development of Jiangsu Higher Education Institutions for financial support. This work was also sponsored by TAPP.
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Xu, H., Li, L., Wang, Z. et al. A green synthesis of 1,7-dihydrodipyrazolo[3,4-b:4′,3′-e]pyridin-3(2H)-one derivatives from deamination cyclization reactions in aqueous medium. Res Chem Intermed 44, 3211–3226 (2018). https://doi.org/10.1007/s11164-018-3302-7
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DOI: https://doi.org/10.1007/s11164-018-3302-7