Copyright (c) 2024 Dr. Ankusab Nadaf
This work is licensed under a Creative Commons Attribution 4.0 International License.
Facile Synthesis of Imidazo[1,2-a]pyridines via LED Light Induced Reaction between 2-Aminopyridines and Acetophenones
Corresponding Author(s) : Ankusab Noorahmadsab Nadaf
Asian Journal of Chemistry,
Vol. 37 No. 1 (2025): Vol 37 Issue 1, 2025
Abstract
Imidazo[1,2-a]pyridines are class of privileged motifs present in various important drugs. The majority of the processes involve metal catalysts, despite the fact that there are substantial benefits to develop new methodologies for the synthesis of imidazo[1,2-a]pyridines. In this work, an eco-friendly method is reported for the synthesis of imidazo[1,2-a]pyridines in the presence of LED light source under ambient conditions. The reaction proceeds smoothly with both electron donating and electron withdrawing groups to afford the products in excellent yields.
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- A.N. Nadaf and K. Shivashankar, Lett. Org. Chem., 15, 676 (2018); https://doi.org/10.2174/1570178615666181107095151
- J. Tiwari, M. Saquib, S. Singh, F. Tufail, M. Singh, J. Singh and J. Singh, Green Chem., 18, 3221 (2016); https://doi.org/10.1039/C5GC02855H
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- N. Hoffmann, Chem. Rev., 108, 1052 (2008); https://doi.org/10.1021/cr0680336
- K. Pericherla, P. Kaswan, P. Khedar, B. Khungar, K. Parang and A. Kumar, RSC Adv., 3, 18923 (2013); https://doi.org/10.1039/c3ra43889a
References
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A. Gueiffier, M. Lhassani, A. Elhakmaoui, R. Snoeck, G. Andrei, O. Chavignon, J.-C. Teulade, A. Kerbal, E.M. Essassi, J.-C. Debouzy, M. Witvrouw, Y. Blache, J. Balzarini, E. De Clercq and J.-P. Chapat, J. Med. Chem., 39, 2856 (1996); https://doi.org/10.1021/jm9507901
A. Gueiffier, S. Mavel, M. Lhassani, A. Elhakmaoui, R. Snoeck, G. Andrei, O. Chavignon, J.-C. Teulade, M. Witvrouw, J. Balzarini, E. De Clercq and J.-P. Chapat, J. Med. Chem., 41, 5108 (1998); https://doi.org/10.1021/jm981051y
Y. Rival, G. Grassy and G. Michel, Chem. Pharm. Bull., 40, 1170 (1992); https://doi.org/10.1248/cpb.40.1170
M.H. Fisher and A. Lusi, J. Med. Chem., 15, 982 (1972); https://doi.org/10.1021/jm00279a026
Y. Rival, A. Taudou and R. Ecalle, Il Farmaco, 48, 857 (1993).
J. Mendlein and G. Sachs, J. Biol. Chem., 265, 5030 (1990); https://doi.org/10.1016/S0021-9258(19)34079-7
Y. Abe, H. Kayakiri, S. Satoh, T. Inoue, Y. Sawada, K. Imai, M. Inamura, M. Asano, C. Hatori, A. Katayama, T. Oku and H. Tanaka, J. Med. Chem., 41, 564 (1998); https://doi.org/10.1021/jm970591c
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J.E. Starrett Jr., T.A. Montzka, A.R. Crosswell and R.L. Cavanagh, J. Med. Chem., 32, 2204 (1989); https://doi.org/10.1021/jm00129a028
A.R. Katritzky, Y.J. Xu and H. Tu, J. Org. Chem., 68, 4935 (2003); https://doi.org/10.1021/jo026797p
N. Devi, R.K. Rawal and V. Singh, Tetrahedron, 71, 183 (2015); https://doi.org/10.1016/j.tet.2014.10.032
B. Yang, C. Tao, T. Shao, J. Gong and C. Che, Beilstein J. Org. Chem., 12, 1487 (2016); https://doi.org/10.3762/bjoc.12.145
C. Blackburn, B. Guan, P. Fleming, K. Shiosaki and S. Tsai, Tetrahedron Lett., 39, 3635 (1998); https://doi.org/10.1016/S0040-4039(98)00653-4
N. Chernyak and V. Gevorgyan, Angew. Chem. Int. Ed., 49, 2743 (2010); https://doi.org/10.1002/anie.200907291
P. Liu, L.-S. Fang, X. Lei and G. Lin, Tetrahedron Lett., 51, 4605 (2010); https://doi.org/10.1016/j.tetlet.2010.05.139
D.K. Nair, S.M. Mobin and I.N.N. Namboothiri, Org. Lett., 14, 4580 (2012); https://doi.org/10.1021/ol3020418
S. Santra, A.K. Bagdi, A. Majee and A. Hajra, Adv. Synth. Catal., 355, 1065 (2013); https://doi.org/10.1002/adsc.201201112
R.-L. Yan, H. Yan, C. Ma, Z.-Y. Ren, X.-A. Gao, G.-S. Huang and Y.-M. Liang, J. Org. Chem., 77, 2024 (2012); https://doi.org/10.1021/jo202447p
J. Zeng, Y.J. Tan, M.L. Leow and X.-W. Liu, Org. Lett., 14, 4386 (2012); https://doi.org/10.1021/ol301858j
P. Liu, C.-L. Deng, X. Lei and G.-Q. Lin, Eur. J. Org. Chem., 2011, 7308 (2011); https://doi.org/10.1002/ejoc.201101053
A.K. Bagdi and A. Hajra, Chem. Rec., 16, 1868 (2016); https://doi.org/10.1002/tcr.201600057
S. Cacchi, L. Caglioti and E. Cernia, Synthesis, 64 (1979); https://doi.org/10.1055/s-1979-28560
L.C. King and G.K. Ostrum, J. Org. Chem., 29, 3459 (1964); https://doi.org/10.1021/jo01035a003
S.J. Pasaribu and L.R. Williams, Aust. J. Chem., 26, 1327 (1973); https://doi.org/10.1071/CH9731327
Z. Fei, Y.P. Zhu, M.C. Liu, F.C. Jia and A.N.I. Wu, Tetrahedron Lett., 54, 1222 (2013); https://doi.org/10.1016/j.tetlet.2012.12.072
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Z.-J. Cai, S.-Y. Wang and S.-J. Ji, Adv. Synth. Catal., 355, 2686 (2013); https://doi.org/10.1002/adsc.201300333
D. Kour, R. Khajuria and K.K. Kapoor, Tetrahedron Lett., 57, 4464 (2016); https://doi.org/10.1016/j.tetlet.2016.08.058
S. Santra, S. Mitra, A.K. Bagdi, A. Majee and A. Hajra, Tetrahedron Lett., 55, 5151 (2014); https://doi.org/10.1016/j.tetlet.2014.07.094
Y. Zhang, Z. Chen, W. Wu, Y. Zhang and W. Su, J. Org. Chem., 78, 12494 (2013); https://doi.org/10.1021/jo402134x
M. Jirasek, K. Strakova, T. Nevesely, E. Svobodova, Z. Rottnerova and R. Cibulka, Eur. J. Org. Chem., 39, 2139 (2017); https://doi.org/10.1002/ejoc.201601377
A. Das, Lett. Org. Chem., 19, 283 (2022); https://doi.org/10.2174/1570178618666210916164132
V. Srivastava, P.K. Singh, S. Kanaujia and P.P. Singh, New J. Chem., 42, 688 (2018); https://doi.org/10.1039/C7NJ03068A
H. Wang, Y. Ren, K. Wang, Y. Man, Y. Xiang, N. Li and B. Tang, Chem. Commun., 53, 9644 (2017); https://doi.org/10.1039/C7CC04911K
V. Srivastava, P.K. Singh, P.P. Singh and Y. Eosin, Croat. Chem. Acta, 88, 59 (2015); https://doi.org/10.5562/cca2520
Y. Zhang, Z. Wang and X. Lang, Catal. Sci. Technol., 7, 4955 (2017); https://doi.org/10.1039/C7CY01510K
A.N. Nadaf and K. Shivashankar, Synth. Commun., 48, 809 (2018); https://doi.org/10.1080/00397911.2018.1426101
A.N. Nadaf and K. Shivashankar, J. Heterocycl. Chem., 55, 1375 (2018); https://doi.org/10.1002/jhet.3171
A.N. Nadaf and K. Shivashankar, Lett. Org. Chem., 15, 676 (2018); https://doi.org/10.2174/1570178615666181107095151
J. Tiwari, M. Saquib, S. Singh, F. Tufail, M. Singh, J. Singh and J. Singh, Green Chem., 18, 3221 (2016); https://doi.org/10.1039/C5GC02855H
D.P. Hari and B. Konig, Org. Lett., 13, 3852 (2011); https://doi.org/10.1021/ol201376v
N. Hoffmann, Chem. Rev., 108, 1052 (2008); https://doi.org/10.1021/cr0680336
K. Pericherla, P. Kaswan, P. Khedar, B. Khungar, K. Parang and A. Kumar, RSC Adv., 3, 18923 (2013); https://doi.org/10.1039/c3ra43889a