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Synthesis of Chromeno/Pyrano-quinolines via Tandem Approach involving Michael Addition-Cyclization Catalyzed by L-Proline/Cu(II)
Corresponding Author(s) : Panaganti Leelavathi
Asian Journal of Chemistry,
Vol. 37 No. 2 (2025): Vol 37 Issue 2, 2025
Abstract
In this study, the reaction of β-nitrovinylquinolines with 1,3-dicarbonyl compounds to furnish chromeno-quinolines under L-proline/Cu(II) catalysis was described. The nitro methyl derivatives of chromeno-quinolines were obtained via the Michael addition followed by the cyclization reaction of cyclic 1,3-dicarbonyl compounds with β-nitrovinylquinolines in a tandem approach. The reaction with open-chain 1,3-dicarbonyl compounds furnished the corresponding aci form of pyranoquinolines.
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- B.S. Matada, R. Pattanashettar and N.G. Yernale, Bioorg. Med. Chem., 32, 115973 (2021); https://doi.org/10.1016/j.bmc.2020.115973
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- J.E. Anthony, Chem. Rev., 106, 5028 (2006); https://doi.org/10.1021/cr050966z
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- C. Marchand, M. Abdelmalak, J. Kankanala, S.-Y. Huang, E. Kiselev, K. Fesen, K. Kurahashi, H. Sasanuma, S. Takeda, H. Aihara, Z. Wang and Y. Pommier, ACS Chem. Biol., 11, 1925 (2016); https://doi.org/10.1021/acschembio.5b01047
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- P.K. Rathod, S. Jonnalagadda and L. Panaganti, Tetrahedron Lett., 66, 152808 (2021); https://doi.org/10.1016/j.tetlet.2020.152808
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- B. List, Chem. Rev., 107, 5413 (2007); https://doi.org/10.1021/cr078412e
- Q. Li, Y. Yan, X. Wang, B. Gong, X. Tang, J. Shi, H. Xu and W. Yi, RSC Adv., 3, 23402 (2013); https://doi.org/10.1039/c3ra43175d
References
B.S. Matada, R. Pattanashettar and N.G. Yernale, Bioorg. Med. Chem., 32, 115973 (2021); https://doi.org/10.1016/j.bmc.2020.115973
A. Weyesa and E. Mulugeta, RSC Adv., 10, 20784 (2020); https://doi.org/10.1039/D0RA03763J
J.E. Anthony, Chem. Rev., 106, 5028 (2006); https://doi.org/10.1021/cr050966z
L. Jacobs, C. de Kock, D. Taylor, S.C. Pelly and M.A.L. Blackie, Bioorg. Med. Chem., 26, 5730 (2018); https://doi.org/10.1016/j.bmc.2018.10.029
N.A. McGrath, M. Brichacek and J.T. Njardarson, J. Chem. Educ., 87, 1348 (2010); https://doi.org/10.1021/ed1003806
R. Watpade, A. Bholay and R. Toche, J. Heterocycl. Chem., 54, 3434 (2017); https://doi.org/10.1002/jhet.2966
M. Abass, A.R.A. Alzandi, M.M. Hassan and N. Mohamed, Polycycl. Aromat. Compd., 41, 2120 (2021); https://doi.org/10.1080/10406638.2019.1710856
I.A. Bala, O.F. Al Sharif, A.M. Asiri and R.M. El-Shishtawy, Results Chem., 7, 101529 (2024); https://doi.org/10.1016/j.rechem.2024.101529
R.A. Mekheimer, M.A. Al-Sheikh, H.Y. Medrasi and K.U. Sadek, RSC Adv., 10, 19867 (2020); https://doi.org/10.1039/D0RA02786C
C. Marchand, M. Abdelmalak, J. Kankanala, S.-Y. Huang, E. Kiselev, K. Fesen, K. Kurahashi, H. Sasanuma, S. Takeda, H. Aihara, Z. Wang and Y. Pommier, ACS Chem. Biol., 11, 1925 (2016); https://doi.org/10.1021/acschembio.5b01047
M. Costa, T. A. Dias, A. Brito and F. Proenca, Eur. J. Med. Chem., 123, 487 (2016); https://doi.org/10.1016/j.ejmech.2016.07.057
A. Chaudhary, K. Singh, N. Verma, S. Kumar, D. Kumar and P.P. Sharma, Mini Rev. Med. Chem., 22, 2736 (2022); https://doi.org/10.2174/1389557522666220331161636
V. Raj and J. Lee, Front Chem., 8, 623 (2020); https://doi.org/10.3389/fchem.2020.00623
P. Patra and G.K. Kar, New J. Chem., 45, 2879 (2021); https://doi.org/10.1039/D0NJ04761A
S. Hosseinzadegan, N. Hazeri, M.T. Maghsoodlou, M. Moghaddam-Manesh and M. Shirzaei, J. Iran. Chem. Soc., 17, 3271 (2020); https://doi.org/10.1007/s13738-020-01990-3
K. Mahesh, K. Ravi, P.K. Rathod and P. Leelavathi, New J. Chem., 44, 2367 (2020); https://doi.org/10.1039/C9NJ05254B
P.K. Rathod, S. Jonnalagadda and L. Panaganti, Tetrahedron Lett., 66, 152808 (2021); https://doi.org/10.1016/j.tetlet.2020.152808
J. Sowmya, B. Padma and P. Leelavathi, J. Indian Chem. Soc., 99, 100279 (2022); https://doi.org/10.1016/j.jics.2021.100279
P. Kumar Rathod, K. Krishnaveni and P. Leelavathi, Tetrahedron Lett., 104, 154028 (2022); https://doi.org/10.1016/j.tetlet.2022.154028
V. Oliveira, M. Cardoso and L. Forezi, Catalysts, 8, 605 (2018); https://doi.org/10.3390/catal8120605
B. List, Chem. Rev., 107, 5413 (2007); https://doi.org/10.1021/cr078412e
Q. Li, Y. Yan, X. Wang, B. Gong, X. Tang, J. Shi, H. Xu and W. Yi, RSC Adv., 3, 23402 (2013); https://doi.org/10.1039/c3ra43175d