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An Efficient, One-Pot Synthesis of 1,3-Disubstituted imidazo[1,5-a]pyridines, Fe(OTf)3 Mediated C-C Bond Formation
Corresponding Author(s) : T. Demappa
Asian Journal of Chemistry,
Vol. 35 No. 5 (2023): Vol 35 Issue 5, 2023
Abstract
A vital approach of Fe(OTf)3 and MS3Å (molecular sieves 3Å) mediated one pot synthesis of 1,3-disubstituted imidazo[1,5-a]pyridines from dithioester, 2-methylaminopyridine and alcohol. This methodology involves the intramolecular cyclization and C–C bond formation under mild condition and operates in a single step yielding the products in good to excellent yields. This protocol was compatible to construct various 1,3-disubstituted imidazo[1,5-a] pyridines derivatives.
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- J. Panda, B.P. Raiguru, M. Mishra, S. Mohapatra and S. Nayak, ChemistrySelect, 7, e202103987 (2022); https://doi.org/10.1002/slct.202103987
- R.Z.U. Kobak and B. Akkurt, J. Turk. Chem. Soc. A, 9, 1335 (2022); https://doi.org/10.18596/jotcsa.1110922
- D. Kim, L. Wang, J.J. Hale, C.L. Lynch, R.J. Budhu, M. MacCoss, S.G. Mills, L. Malkowitz, S.L. Gould, J.A. DeMartino, M.S. Springer, D. Hazuda, M. Miller, J. Kessler, R.C. Hrin, G. Carver, A. Carella, K. Henry, J. Lineberger, W.A. Schleif and E.A. Emini, Bioorg. Med. Chem. Lett., 15, 2129 (2005); https://doi.org/10.1016/j.bmcl.2005.02.030
- R. Nirogi, A.R. Mohammed, A.K. Shinde, S.R. Gagginapally, D.M. Kancharla, V.R. Middekadi, N. Bogaraju, S.R. Ravella, P. Singh, S.R. Birangal, R. Subramanian, R.C. Palacharla, V. Benade, N. Muddana and P. Jayarajan, J. Med. Chem., 61, 4993 (2018); https://doi.org/10.1021/acs.jmedchem.8b00457
- D.R. Mohbiya and N. Sekar, ChemistrySelect, 3, 1635 (2018); https://doi.org/10.1002/slct.201702579
- L.A. Sorbera, J. Castaner and P.A. Leeson, Drugs Future, 27, 935 (2002); https://doi.org/10.1358/dof.2002.027.10.701186
- J. Liu, Y. Cao, L. Li, H. Pei, Y. Chen, J. Hu, Y. Qin, Y. Li, W. Li and W. Liu, RSC Adv., 5, 10318 (2015); https://doi.org/10.1039/C4RA14692A
- C.-W. Hsia, M. Velusamy, J.-T. Tsao, C.-H. Hsia, D.-S. Chou, T. Jayakumar, L.-W. Lee, J.-Y. Li and J.-R. Sheu, Int. J. Mol. Sci., 18, 2616 (2017); https://doi.org/10.3390/ijms18122616
- R. Nirogi, A.R. Mohammed, A.K. Shinde, N. Bogaraju, S.R. Gagginapalli, S.R. Ravella, L. Kota, G. Bhyrapuneni, N.R. Muddana, V. Benade, R.C. Palacharla, P. Jayarajan, R. Subramanian and V.K. Goyal, Eur. J. Med. Chem., 103, 289 (2015); https://doi.org/10.1016/j.ejmech.2015.08.051
- M.D. Weber, C. Garino, G. Volpi, E. Casamassa, M. Milanesio, C. Barolo and R.D. Costa, Dalton Trans., 45, 8984 (2016); https://doi.org/10.1039/C6DT00970K
- H. Sheng, Y. Hu, Y. Zhou, S. Fan, Y. Cao, X. Zhao and W. Yang, Dyes Pigments, 160, 48 (2019); https://doi.org/10.1016/j.dyepig.2018.07.036
- F. Yagishita, C. Nii, Y. Tezuka, A. Tabata, H. Nagamune, N. Uemura, Y. Yoshida, T. Mino, M. Sakamoto and Y. Kawamura, Asian J. Org. Chem., 7, 1614 (2018); https://doi.org/10.1002/ajoc.201800250
- S.-L. Shen, X.-Q. Huang, Y.-Y. Zhang, Y. Zhu, C. Hou, Y.-Q. Ge and X.-Q. Cao, Sens. Actuators B Chem., 263, 252 (2018); https://doi.org/10.1016/j.snb.2018.02.121
- Y. Ge, R. Ji, S. Shen, X. Cao and F. Li, Sens. Actuators B Chem., 245, 875 (2017); https://doi.org/10.1016/j.snb.2017.01.169
- A. Fattori, R. Majer, A. Mazzanti, M.F. Ottaviani, A. Modelli, F. Mantellini and S. Santeusanio, Dyes Pigments, 145, 246 (2017); https://doi.org/10.1016/j.dyepig.2017.05.058
- L. Salassa, C. Garino, A. Albertino, G. Volpi, C. Nervi, R. Gobetto and K.I. Hardcastle, Organometallics, 27, 1427 (2008); https://doi.org/10.1021/om701175z
- H. Reimlinger and W.R.F. Lingier, Chem. Ber., 108, 3787 (1975); https://doi.org/10.1002/cber.19751081212
- S.W. Schneller and D.G. Bartholomew, J. Heterocycl. Chem., 15, 439 (1978); https://doi.org/10.1002/jhet.5570150315
- K. Mantelingu, Y. Lin and D. Seidel, Org. Lett., 16, 5910 (2014); https://doi.org/10.1021/ol502918g
- A.B. Ramesha, G.M. Raghavendra, K.N. Nandeesh, K.S. Rangappa and K. Mantelingu, Tetrahedron Lett., 54, 95 (2013); https://doi.org/10.1016/j.tetlet.2012.10.112
- A.B. Ramesha, N.C. Sandhya, C.S. Pavan Kumar, M. Hiremath, K. Mantelingu and K.S. Rangappa, New J. Chem., 40, 7637 (2016); https://doi.org/10.1039/C6NJ01038E
- T.A. Jenifer Vijay, K.N. Nandeesh, G.M. Raghavendra, K.S. Rangappa and K. Mantelingu, Tetrahedron Lett., 54, 6533 (2013); https://doi.org/10.1016/j.tetlet.2013.09.094
- N.C. Sandhya, K.N. Nandeesh, K.S. Rangappa and S. Ananda, RSC Adv., 5, 29939 (2015); https://doi.org/10.1039/C5RA02114F
- A.B. Ramesha, C.S. Pavan Kumar, N.C. Sandhya, M.N. Kumara, K. Mantelingu and K.S. Rangappa, RSC Adv., 6, 48375 (2016); https://doi.org/10.1039/C6RA03771B
- H.A. Swarup, N. Chaithra, K. Mantelingu and K.S. Rangappa, ChemistrySelect, 3, 5390 (2018); https://doi.org/10.1002/slct.201800886
- S. Cheruku, C. Nagaraju, P. Shetty, S. Hassan A, S. Nagarakere C, K. Manikyanally N and M. Kempegowda, Synth. Commun., 50, 1486 (2020); https://doi.org/10.1080/00397911.2020.1743319
References
J. Panda, B.P. Raiguru, M. Mishra, S. Mohapatra and S. Nayak, ChemistrySelect, 7, e202103987 (2022); https://doi.org/10.1002/slct.202103987
R.Z.U. Kobak and B. Akkurt, J. Turk. Chem. Soc. A, 9, 1335 (2022); https://doi.org/10.18596/jotcsa.1110922
D. Kim, L. Wang, J.J. Hale, C.L. Lynch, R.J. Budhu, M. MacCoss, S.G. Mills, L. Malkowitz, S.L. Gould, J.A. DeMartino, M.S. Springer, D. Hazuda, M. Miller, J. Kessler, R.C. Hrin, G. Carver, A. Carella, K. Henry, J. Lineberger, W.A. Schleif and E.A. Emini, Bioorg. Med. Chem. Lett., 15, 2129 (2005); https://doi.org/10.1016/j.bmcl.2005.02.030
R. Nirogi, A.R. Mohammed, A.K. Shinde, S.R. Gagginapally, D.M. Kancharla, V.R. Middekadi, N. Bogaraju, S.R. Ravella, P. Singh, S.R. Birangal, R. Subramanian, R.C. Palacharla, V. Benade, N. Muddana and P. Jayarajan, J. Med. Chem., 61, 4993 (2018); https://doi.org/10.1021/acs.jmedchem.8b00457
D.R. Mohbiya and N. Sekar, ChemistrySelect, 3, 1635 (2018); https://doi.org/10.1002/slct.201702579
L.A. Sorbera, J. Castaner and P.A. Leeson, Drugs Future, 27, 935 (2002); https://doi.org/10.1358/dof.2002.027.10.701186
J. Liu, Y. Cao, L. Li, H. Pei, Y. Chen, J. Hu, Y. Qin, Y. Li, W. Li and W. Liu, RSC Adv., 5, 10318 (2015); https://doi.org/10.1039/C4RA14692A
C.-W. Hsia, M. Velusamy, J.-T. Tsao, C.-H. Hsia, D.-S. Chou, T. Jayakumar, L.-W. Lee, J.-Y. Li and J.-R. Sheu, Int. J. Mol. Sci., 18, 2616 (2017); https://doi.org/10.3390/ijms18122616
R. Nirogi, A.R. Mohammed, A.K. Shinde, N. Bogaraju, S.R. Gagginapalli, S.R. Ravella, L. Kota, G. Bhyrapuneni, N.R. Muddana, V. Benade, R.C. Palacharla, P. Jayarajan, R. Subramanian and V.K. Goyal, Eur. J. Med. Chem., 103, 289 (2015); https://doi.org/10.1016/j.ejmech.2015.08.051
M.D. Weber, C. Garino, G. Volpi, E. Casamassa, M. Milanesio, C. Barolo and R.D. Costa, Dalton Trans., 45, 8984 (2016); https://doi.org/10.1039/C6DT00970K
H. Sheng, Y. Hu, Y. Zhou, S. Fan, Y. Cao, X. Zhao and W. Yang, Dyes Pigments, 160, 48 (2019); https://doi.org/10.1016/j.dyepig.2018.07.036
F. Yagishita, C. Nii, Y. Tezuka, A. Tabata, H. Nagamune, N. Uemura, Y. Yoshida, T. Mino, M. Sakamoto and Y. Kawamura, Asian J. Org. Chem., 7, 1614 (2018); https://doi.org/10.1002/ajoc.201800250
S.-L. Shen, X.-Q. Huang, Y.-Y. Zhang, Y. Zhu, C. Hou, Y.-Q. Ge and X.-Q. Cao, Sens. Actuators B Chem., 263, 252 (2018); https://doi.org/10.1016/j.snb.2018.02.121
Y. Ge, R. Ji, S. Shen, X. Cao and F. Li, Sens. Actuators B Chem., 245, 875 (2017); https://doi.org/10.1016/j.snb.2017.01.169
A. Fattori, R. Majer, A. Mazzanti, M.F. Ottaviani, A. Modelli, F. Mantellini and S. Santeusanio, Dyes Pigments, 145, 246 (2017); https://doi.org/10.1016/j.dyepig.2017.05.058
L. Salassa, C. Garino, A. Albertino, G. Volpi, C. Nervi, R. Gobetto and K.I. Hardcastle, Organometallics, 27, 1427 (2008); https://doi.org/10.1021/om701175z
H. Reimlinger and W.R.F. Lingier, Chem. Ber., 108, 3787 (1975); https://doi.org/10.1002/cber.19751081212
S.W. Schneller and D.G. Bartholomew, J. Heterocycl. Chem., 15, 439 (1978); https://doi.org/10.1002/jhet.5570150315
K. Mantelingu, Y. Lin and D. Seidel, Org. Lett., 16, 5910 (2014); https://doi.org/10.1021/ol502918g
A.B. Ramesha, G.M. Raghavendra, K.N. Nandeesh, K.S. Rangappa and K. Mantelingu, Tetrahedron Lett., 54, 95 (2013); https://doi.org/10.1016/j.tetlet.2012.10.112
A.B. Ramesha, N.C. Sandhya, C.S. Pavan Kumar, M. Hiremath, K. Mantelingu and K.S. Rangappa, New J. Chem., 40, 7637 (2016); https://doi.org/10.1039/C6NJ01038E
T.A. Jenifer Vijay, K.N. Nandeesh, G.M. Raghavendra, K.S. Rangappa and K. Mantelingu, Tetrahedron Lett., 54, 6533 (2013); https://doi.org/10.1016/j.tetlet.2013.09.094
N.C. Sandhya, K.N. Nandeesh, K.S. Rangappa and S. Ananda, RSC Adv., 5, 29939 (2015); https://doi.org/10.1039/C5RA02114F
A.B. Ramesha, C.S. Pavan Kumar, N.C. Sandhya, M.N. Kumara, K. Mantelingu and K.S. Rangappa, RSC Adv., 6, 48375 (2016); https://doi.org/10.1039/C6RA03771B
H.A. Swarup, N. Chaithra, K. Mantelingu and K.S. Rangappa, ChemistrySelect, 3, 5390 (2018); https://doi.org/10.1002/slct.201800886
S. Cheruku, C. Nagaraju, P. Shetty, S. Hassan A, S. Nagarakere C, K. Manikyanally N and M. Kempegowda, Synth. Commun., 50, 1486 (2020); https://doi.org/10.1080/00397911.2020.1743319