Copyright (c) 2024 Om Prakash Joshi, Ankit Kumar Dash, Ramalingam Thirumoorthi, Chandrakanta Dash
This work is licensed under a Creative Commons Attribution 4.0 International License.
Iron-Catalyzed Annulation of 2-Aminobenzaldehydes with Iodonium Ylides: A Mild and General Route for the Synthesis of Acridinone Derivatives
Corresponding Author(s) : Chandrakanta Dash
Asian Journal of Chemistry,
Vol. 36 No. 6 (2024): Vol 36 Issue 6, 2024
Abstract
An inexpensive iron-catalyzed annulation of 2-aminobenzaldehydes with iodonium ylides for the synthesis of acridinone derivatives was reported. A library of biologically relevant 3,4-dihydropyridine-1-one scaffold was synthesized by the reaction of corresponding 2-amino benzaldehyde and iodonium ylides under mild reaction conditions in a green solvent. The reaction tolerates various alkyl, aryl and halogenated substrates and affords the desired product in moderate to good yields. The reported reaction has an inexpensive catalytic system, mild reaction conditions, easily accessible substrates and the use of green solvents.
Keywords
Download Citation
Endnote/Zotero/Mendeley (RIS)BibTeX
- Z.-H. Yu, H.-F. Zheng, W. Yuan, Z.-L. Tang, A.-D. Zhang and D.-Q. Shi, Tetrahedron, 69, 8137 (2013); https://doi.org/10.1016/j.tet.2013.07.050
- C.-C. Wang, C.-K. Chan and C.-Y. Lai, Synthesis, 52, 1779 (2020); https://doi.org/10.1055/s-0039-1690088
- V. Sridharan, P. Ribelles, M.T. Ramos and J.C. Menéndez, J. Org. Chem., 74, 5715 (2009); https://doi.org/10.1021/jo900965f
- R.R. Rajawinslin, S.D. Gawande, V. Kavala, Y.-H. Huang, C.-W. Kuo, T.-S. Kuo, M.-L. Chen, C.-H. He and C.-F. Yao, RSC Adv., 4, 37806 (2014); https://doi.org/10.1039/C4RA06410K
- N. Yadav, K. Gopalaiah, J. Pandey and R. Nagarajan, Dalton Trans., 52, 5969 (2023); https://doi.org/10.1039/D3DT00435J
- A.S. Oyedele, D.N. Bogan and C.O. Okoro, Bioorg. Med. Chem., 28, 115426 (2020); https://doi.org/10.1016/j.bmc.2020.115426
- P. Lv, C.-L. Xia, N. Wang, Z.-Q. Liu, Z.-S. Huang and S.-L. Huang, Bioorg. Med. Chem., 26, 4693 (2018); https://doi.org/10.1016/j.bmc.2018.08.007
- J. Marco-Contelles, E. Pérez-Mayoral, A. Samadi, M.C. Carreiras and E. Soriano, Chem. Rev., 109, 2652 (2009); https://doi.org/10.1021/cr800482c
- N. Paul, S. Muthusubramanian and N. Bhuvanesh, New J. Chem., 35, 2607 (2011); https://doi.org/10.1039/c1nj20539k
- R.R. Rajawinslin, S.S. Ichake, V. Kavala, S.D. Gawande, Y.-H. Huang, C.-W. Kuo and C.-F. Yao, RSC Adv., 5, 52141 (2015); https://doi.org/10.1039/C5RA06395G
- M.P. Maguire, K.R. Sheets, K. McVety, A.P. Spada and A. Zilberstein, J. Med. Chem., 37, 2129 (1994); https://doi.org/10.1021/jm00040a003
- A. Arcadi, M. Chiarini, S. Di Giuseppe and F. Marinelli, Synlett, 2003, 203 (2003); https://doi.org/10.1055/s-2003-36798
- J.S. Yadav, B.V.S. Reddy and K. Premalatha, Synlett, 2004, 963 (2004); https://doi.org/10.1055/s-2004-822898
- J. Wang, X. Fan, X. Zhang and L. Han, Can. J. Chem., 82, 1192 (2004); https://doi.org/10.1139/v04-066
- P. Arumugam, G. Karthikeyan, R. Atchudan, D. Muralidharan and P.T. Perumal, Chem. Lett., 34, 314 (2005); https://doi.org/10.1246/cl.2005.314
- S.K. De and R.A. Gibbs, Tetrahedron Lett., 46, 1647 (2005); https://doi.org/10.1016/j.tetlet.2005.01.075
- D.S. Bose and R.K. Kumar, Tetrahedron Lett., 47, 813 (2006); https://doi.org/10.1016/j.tetlet.2005.11.075
- E. Soleimani, M.M. Khodaei, N. Batooie and S. Samadi, Chem. Pharm. Bull. (Tokyo), 58, 212 (2010); https://doi.org/10.1248/cpb.58.212
- S. Genovese, F. Epifano, M.C. Marcotullio, C. Pelucchini and M. Curini, Tetrahedron Lett., 52, 3474 (2011); https://doi.org/10.1016/j.tetlet.2011.04.109
- B. Tanwar, D. Kumar, A. Kumar, M.I. Ansari, M.M. Qadri, M.D. Vaja, M. Singh and A.K. Chakraborti, New J. Chem., 39, 9824 (2015); https://doi.org/10.1039/C5NJ02010G
- S. Telu, S. Durmus and G.F. Koser, Tetrahedron Lett., 48, 1863 (2007); https://doi.org/10.1016/j.tetlet.2006.12.132
- A. Antos, Y. Elemes, A. Michaelides, J.A. Nyxas, S. Skoulika and L.P. Hadjiarapoglou, J. Org. Chem., 77, 10949 (2012); https://doi.org/10.1021/jo3020787
- S. Mo, X. Li and J. Xu, J. Org. Chem., 79, 9186 (2014); https://doi.org/10.1021/jo501628h
- A. Yoshimura and V.V. Zhdankin, Chem. Rev., 116, 3328 (2016); https://doi.org/10.1021/acs.chemrev.5b00547
- M.B. Camacho, A.E. Clark, T.A. Liebrecht and J.P. DeLuca, J. Am. Chem. Soc., 122, 5210 (2000); https://doi.org/10.1021/ja000334o
- R.M. Moriarty, S. Tyagi and M. Kinch, Tetrahedron, 66, 5801 (2010); https://doi.org/10.1016/j.tet.2010.05.005
- F.-X. Felpin and S. Sengupta, Chem. Soc. Rev., 48, 1150 (2019); https://doi.org/10.1039/C8CS00453F
- X. Yao, X. Shan and L. Zu, Org. Lett., 20, 6498 (2018); https://doi.org/10.1021/acs.orglett.8b02823
- S. Mayakrishnan, M. Tamizmani and N.U. Maheswari, Chem. Commun. (Camb.), 56, 15462 (2020); https://doi.org/10.1039/D0CC06038K
- Z.-P. Han, M.-M. Xu, R.-Y. Zhang, X.-P. Xu and S.-J. Ji, Green Chem., 23, 6337 (2021); https://doi.org/10.1039/D1GC01820E
- X.-C. Huang, Y.-L. Liu, Y. Liang, S.-F. Pi, F. Wang and J.-H. Li, Org. Lett., 10, 1525 (2008); https://doi.org/10.1021/ol800051k
- R.M. Moriarty, S. Tyagi, D. Ivanov and M. Constantinescu, J. Am. Chem. Soc., 130, 7564 (2008); https://doi.org/10.1021/ja802735f
- S. Nunewar, S. Kumar, H. Pandhare, S. Nanduri and V. Kanchupalli, Org. Lett., 23, 4233 (2021); https://doi.org/10.1021/acs.orglett.1c01167
- S. Kumar, V. Borkar, M. Mujahid, S. Nunewar and V. Kanchupalli, Org. Biomol. Chem., 21, 24 (2022); https://doi.org/10.1039/D2OB01644C
- X. Li, Y. Shen, G. Zhang, X. Zheng, Q. Zhao and Z. Song, Org. Lett., 24, 5281 (2022); https://doi.org/10.1021/acs.orglett.2c01843
- H. Li, H. Gu, Y. Lu, N. Xu, N. Han, J. Li, J. Liu and J. Liu, J. Org. Chem., 87, 8142 (2022); https://doi.org/10.1021/acs.joc.2c00852
- C. Liu, Q. Dai, Y. Li, C. Huang, L. Guo and Z. Yang, J. Org. Chem., 88, 7281 (2023); https://doi.org/10.1021/acs.joc.3c00517
- X. Liu, B. Zhou, K. Yan, J. Wen, Q. Li, X. Wang and X. Wang, Adv. Synth. Catal., 366, 1744 (2024); https://doi.org/10.1002/adsc.202301451
- G.R. Fulmer, A.J.M. Miller, N.H. Sherden, H.E. Gottlieb, A. Nudelman, B.M. Stoltz, J.E. Bercaw and K.I. Goldberg, Organometallics, 29, 2176 (2010); https://doi.org/10.1021/om100106e
- B. Kaewmee, V. Rukachaisirikul and J. Kaeobamrung, Org. Biomol. Chem., 15, 7387 (2017); https://doi.org/10.1039/C7OB01867C
- E. Cini, E. Petricci, G.I. Truglio, M. Vecchio and M. Taddei, RSC Advances, 6, 31386 (2016); https://doi.org/10.1039/C6RA03585J
- A.M. Pandey, N.K. Digrawal, N. Mohanta, A.B. Jamdade, M.B. Chaudhari, G.S. Bisht and B. Gnanaprakasam, J. Org. Chem., 86, 8805 (2021); https://doi.org/10.1021/acs.joc.1c00714
- H. Li, B. Song, M. Mahmut and M. Imerhasan, Curr. Org. Synth., 18, 399 (2021); https://doi.org/10.2174/1570179417666201228165500
- M. Godino-Ojer, A.J. López-Peinado, R.M. Martín-Aranda, J. Przepiórski, E. Pérez-Mayoral and E. Soriano, ChemCatChem, 6, 3440 (2014); https://doi.org/10.1002/cctc.201402602
References
Z.-H. Yu, H.-F. Zheng, W. Yuan, Z.-L. Tang, A.-D. Zhang and D.-Q. Shi, Tetrahedron, 69, 8137 (2013); https://doi.org/10.1016/j.tet.2013.07.050
C.-C. Wang, C.-K. Chan and C.-Y. Lai, Synthesis, 52, 1779 (2020); https://doi.org/10.1055/s-0039-1690088
V. Sridharan, P. Ribelles, M.T. Ramos and J.C. Menéndez, J. Org. Chem., 74, 5715 (2009); https://doi.org/10.1021/jo900965f
R.R. Rajawinslin, S.D. Gawande, V. Kavala, Y.-H. Huang, C.-W. Kuo, T.-S. Kuo, M.-L. Chen, C.-H. He and C.-F. Yao, RSC Adv., 4, 37806 (2014); https://doi.org/10.1039/C4RA06410K
N. Yadav, K. Gopalaiah, J. Pandey and R. Nagarajan, Dalton Trans., 52, 5969 (2023); https://doi.org/10.1039/D3DT00435J
A.S. Oyedele, D.N. Bogan and C.O. Okoro, Bioorg. Med. Chem., 28, 115426 (2020); https://doi.org/10.1016/j.bmc.2020.115426
P. Lv, C.-L. Xia, N. Wang, Z.-Q. Liu, Z.-S. Huang and S.-L. Huang, Bioorg. Med. Chem., 26, 4693 (2018); https://doi.org/10.1016/j.bmc.2018.08.007
J. Marco-Contelles, E. Pérez-Mayoral, A. Samadi, M.C. Carreiras and E. Soriano, Chem. Rev., 109, 2652 (2009); https://doi.org/10.1021/cr800482c
N. Paul, S. Muthusubramanian and N. Bhuvanesh, New J. Chem., 35, 2607 (2011); https://doi.org/10.1039/c1nj20539k
R.R. Rajawinslin, S.S. Ichake, V. Kavala, S.D. Gawande, Y.-H. Huang, C.-W. Kuo and C.-F. Yao, RSC Adv., 5, 52141 (2015); https://doi.org/10.1039/C5RA06395G
M.P. Maguire, K.R. Sheets, K. McVety, A.P. Spada and A. Zilberstein, J. Med. Chem., 37, 2129 (1994); https://doi.org/10.1021/jm00040a003
A. Arcadi, M. Chiarini, S. Di Giuseppe and F. Marinelli, Synlett, 2003, 203 (2003); https://doi.org/10.1055/s-2003-36798
J.S. Yadav, B.V.S. Reddy and K. Premalatha, Synlett, 2004, 963 (2004); https://doi.org/10.1055/s-2004-822898
J. Wang, X. Fan, X. Zhang and L. Han, Can. J. Chem., 82, 1192 (2004); https://doi.org/10.1139/v04-066
P. Arumugam, G. Karthikeyan, R. Atchudan, D. Muralidharan and P.T. Perumal, Chem. Lett., 34, 314 (2005); https://doi.org/10.1246/cl.2005.314
S.K. De and R.A. Gibbs, Tetrahedron Lett., 46, 1647 (2005); https://doi.org/10.1016/j.tetlet.2005.01.075
D.S. Bose and R.K. Kumar, Tetrahedron Lett., 47, 813 (2006); https://doi.org/10.1016/j.tetlet.2005.11.075
E. Soleimani, M.M. Khodaei, N. Batooie and S. Samadi, Chem. Pharm. Bull. (Tokyo), 58, 212 (2010); https://doi.org/10.1248/cpb.58.212
S. Genovese, F. Epifano, M.C. Marcotullio, C. Pelucchini and M. Curini, Tetrahedron Lett., 52, 3474 (2011); https://doi.org/10.1016/j.tetlet.2011.04.109
B. Tanwar, D. Kumar, A. Kumar, M.I. Ansari, M.M. Qadri, M.D. Vaja, M. Singh and A.K. Chakraborti, New J. Chem., 39, 9824 (2015); https://doi.org/10.1039/C5NJ02010G
S. Telu, S. Durmus and G.F. Koser, Tetrahedron Lett., 48, 1863 (2007); https://doi.org/10.1016/j.tetlet.2006.12.132
A. Antos, Y. Elemes, A. Michaelides, J.A. Nyxas, S. Skoulika and L.P. Hadjiarapoglou, J. Org. Chem., 77, 10949 (2012); https://doi.org/10.1021/jo3020787
S. Mo, X. Li and J. Xu, J. Org. Chem., 79, 9186 (2014); https://doi.org/10.1021/jo501628h
A. Yoshimura and V.V. Zhdankin, Chem. Rev., 116, 3328 (2016); https://doi.org/10.1021/acs.chemrev.5b00547
M.B. Camacho, A.E. Clark, T.A. Liebrecht and J.P. DeLuca, J. Am. Chem. Soc., 122, 5210 (2000); https://doi.org/10.1021/ja000334o
R.M. Moriarty, S. Tyagi and M. Kinch, Tetrahedron, 66, 5801 (2010); https://doi.org/10.1016/j.tet.2010.05.005
F.-X. Felpin and S. Sengupta, Chem. Soc. Rev., 48, 1150 (2019); https://doi.org/10.1039/C8CS00453F
X. Yao, X. Shan and L. Zu, Org. Lett., 20, 6498 (2018); https://doi.org/10.1021/acs.orglett.8b02823
S. Mayakrishnan, M. Tamizmani and N.U. Maheswari, Chem. Commun. (Camb.), 56, 15462 (2020); https://doi.org/10.1039/D0CC06038K
Z.-P. Han, M.-M. Xu, R.-Y. Zhang, X.-P. Xu and S.-J. Ji, Green Chem., 23, 6337 (2021); https://doi.org/10.1039/D1GC01820E
X.-C. Huang, Y.-L. Liu, Y. Liang, S.-F. Pi, F. Wang and J.-H. Li, Org. Lett., 10, 1525 (2008); https://doi.org/10.1021/ol800051k
R.M. Moriarty, S. Tyagi, D. Ivanov and M. Constantinescu, J. Am. Chem. Soc., 130, 7564 (2008); https://doi.org/10.1021/ja802735f
S. Nunewar, S. Kumar, H. Pandhare, S. Nanduri and V. Kanchupalli, Org. Lett., 23, 4233 (2021); https://doi.org/10.1021/acs.orglett.1c01167
S. Kumar, V. Borkar, M. Mujahid, S. Nunewar and V. Kanchupalli, Org. Biomol. Chem., 21, 24 (2022); https://doi.org/10.1039/D2OB01644C
X. Li, Y. Shen, G. Zhang, X. Zheng, Q. Zhao and Z. Song, Org. Lett., 24, 5281 (2022); https://doi.org/10.1021/acs.orglett.2c01843
H. Li, H. Gu, Y. Lu, N. Xu, N. Han, J. Li, J. Liu and J. Liu, J. Org. Chem., 87, 8142 (2022); https://doi.org/10.1021/acs.joc.2c00852
C. Liu, Q. Dai, Y. Li, C. Huang, L. Guo and Z. Yang, J. Org. Chem., 88, 7281 (2023); https://doi.org/10.1021/acs.joc.3c00517
X. Liu, B. Zhou, K. Yan, J. Wen, Q. Li, X. Wang and X. Wang, Adv. Synth. Catal., 366, 1744 (2024); https://doi.org/10.1002/adsc.202301451
G.R. Fulmer, A.J.M. Miller, N.H. Sherden, H.E. Gottlieb, A. Nudelman, B.M. Stoltz, J.E. Bercaw and K.I. Goldberg, Organometallics, 29, 2176 (2010); https://doi.org/10.1021/om100106e
B. Kaewmee, V. Rukachaisirikul and J. Kaeobamrung, Org. Biomol. Chem., 15, 7387 (2017); https://doi.org/10.1039/C7OB01867C
E. Cini, E. Petricci, G.I. Truglio, M. Vecchio and M. Taddei, RSC Advances, 6, 31386 (2016); https://doi.org/10.1039/C6RA03585J
A.M. Pandey, N.K. Digrawal, N. Mohanta, A.B. Jamdade, M.B. Chaudhari, G.S. Bisht and B. Gnanaprakasam, J. Org. Chem., 86, 8805 (2021); https://doi.org/10.1021/acs.joc.1c00714
H. Li, B. Song, M. Mahmut and M. Imerhasan, Curr. Org. Synth., 18, 399 (2021); https://doi.org/10.2174/1570179417666201228165500
M. Godino-Ojer, A.J. López-Peinado, R.M. Martín-Aranda, J. Przepiórski, E. Pérez-Mayoral and E. Soriano, ChemCatChem, 6, 3440 (2014); https://doi.org/10.1002/cctc.201402602