Copyright (c) 2020 AJC
This work is licensed under a Creative Commons Attribution 4.0 International License.
SnCl2 Catalyzed Direct Synthesis of Pyrroles under Aqueous Conditions
Corresponding Author(s) : D. Tejeswararao
Asian Journal of Chemistry,
Vol. 32 No. 4 (2020): Vol 32 Issue 4, 2020
Abstract
Synthetic substituted pyrroles are related with interesting biological activities, yet they remain inadequately explored within drug discovery. Late years have seen a growing interest in synthetic approaches that can provide access to structurally novel pyrroles so that the biological usefulness of this compound class can be more fully investigated. Herein, an efficient and versatile practical protocol for the pyrroles using stannous(II) chloride dihydrate as catalyst is described under aqueous conditions at 55 ºC in high yields. Also, this method is applicable for the preparation of diversity and oriented pyrrole derivatives.
Keywords
Download Citation
Endnote/Zotero/Mendeley (RIS)BibTeX
- C.T. Walsh, S. Garneau Tsodikova and A.R. Howard Jones, Nat. Prod. Rep., 23, 517 (2006); https://doi.org/10.1039/b605245m
- D. Tzankova, S. Vladimirova, L. Peikova and M. Georgieva, J. Chem. Technol. Metall., 53, 451 (2018).
- H. Hoffmann and T. Lindel, Synthesis, 1753 (2003); https://doi.org/10.1055/s-2003-41005
- J.W. Huffman, Curr. Med. Chem., 6, 705 (1999).
- A. Hall, S. Atkinson, S.H. Brown, I.P. Chessell, A. Chowdhury, G.M.P. Giblin, P. Goldsmith, M.P. Healy, K.S. Jandu, M.R. Johnson, A.D. Michel, A. Naylor and J.A. Sweeting, Bioorg. Med. Chem. Lett., 17, 1200 (2007); https://doi.org/10.1016/j.bmcl.2006.12.021
- R.B. Thompson, FASEB J., 15, 1671 (2001); https://doi.org/10.1096/fj.01-0024lsf
- D. Tejeswararao, J. Chil. Chem. Soc., 61, 2843 (2016); https://doi.org/10.4067/S0717-97072016000100018
- P. Plitt, D.E. Gross, M.V. Lynch and J.L. Sessler, Chem. Eur. J., 13, 1374 (2007); https://doi.org/10.1002/chem.200601514
- K. Kumar, S.S. More, S. Goyal, M. Gangar, G.L. Khatik, R.K. Rawal and V.A. Nair, Tetrahedron Lett., 57, 2315 (2016);
- https://doi.org/10.1016/j.tetlet.2016.04.056 10. K. Ogawa and R.C. Rasmussen, J. Org. Chem., 68, 2921 (2003); https://doi.org/10.1021/jo034078k
- D.W. Yoon, H. Hwang and C.H. Lee, Angew. Chem. Int. Ed., 41, 1757 (2002); https://doi.org/10.1002/1521-3773(20020517)41:10<1757::AIDANIE1757>3.0.CO;2-0
- C.F. Lee, L.M. Yang, T.Y. Hwu, A.S. Feng, J.C. Tseng and T.Y. Luh, J. Am. Chem. Soc., 122, 4992 (2000); https://doi.org/10.1021/ja0004736
- R.W. Burli, D. McMinn, J.A. Kaizerman, W. Hu, Y. Ge, Q. Pack, V. Jiang, M. Gross, M. Garcia, R. Tanaka and H.E. Moser, Bioorg. Med. Chem. Lett., 14, 1253 (2004); https://doi.org/10.1016/j.bmcl.2003.12.042
- R.W. Burli, P. Jones, D. McMinn, Q. Le, J.X. Duan, J.A. Kaizerman, S. Difuntorum and H.E. Moser, Bioorg. Med. Chem. Lett., 14, 1259 (2004); https://doi.org/10.1016/j.bmcl.2003.12.043
- M. Del Poeta, W.A. Schell, C.C. Dykstra, S. Jones, R.R. Tidwell, A. Czarny, M. Bajic, M. Bajic, A. Kumar, D. Boykin and J.R. Perfect, Antimicrob. Agents Chemother., 42, 2495 (1998); https://doi.org/10.1128/AAC.42.10.2495
- E. Toja, D. Selva and P. Schiatti, J. Med. Chem., 27, 610 (1984); https://doi.org/10.1021/jm00371a010
- V.J. Demopoulos and E. Rekka, J. Pharm. Sci., 84, 79 (1995); https://doi.org/10.1002/jps.2600840119
- A.S. Girgis, J. Stawinski, N.S. Ismail and H. Farag, Eur. J. Med. Chem., 47, 312 (2012); https://doi.org/10.1016/j.ejmech.2011.10.058
- J. Lehuede, B. Fauconneau, L. Barrier, M. Ourakow, A. Piriou and J.M. Vierfond, Eur. J. Med. Chem., 34, 991 (1999); https://doi.org/10.1016/S0223-5234(99)00111-7
- R. Chesworth, M.D. Wessel, L. Heyden, F.M. Mangano, M. Zawistoski, L. Gegnas, D. Galluzzo, B. Lefker, K.O. Cameron, J. Tickner, B. Lu, T.A. Castleberry, D.N. Petersen, A. Brault, P. Perry, O. Ng, T.A. Owen, L. Pan, H.Z. Ke, T.A. Brown, D.D. Thompson and P. DaSilva Jardine, Bioorg. Med. Chem. Lett., 15, 5562 (2005); https://doi.org/10.1016/j.bmcl.2005.08.010
- K. Liu, H. Lu, L. Hou, Z. Qi, C. Teixeira, F. Barbault, B.-T. Fan, S. Liu, S. Jiang and L. Xie, J. Med. Chem., 51, 7843 (2008); https://doi.org/10.1021/jm800869t
- V.F. Ferreira, M.C.B.V. de Souza, A.C. Cunha, L.O.R. Pereira and M.L.G. Ferreira, Org. Prep. Proced. Int., 33, 411 (2001); https://doi.org/10.1080/00304940109356613
- T.L.J. Gilchrist, Chem. Soc. Perkin Trans. I, 615 (1998); https://doi.org/10.1039/a704493c
- R.K. Dieter and H. Yu, Org. Lett., 2, 2283 (2000); https://doi.org/10.1021/ol006050q
- N. Iwasawa, K. Maeyama and M. Saitou, J. Am. Chem. Soc., 119, 1486 (1997); https://doi.org/10.1021/ja962173n
- A. Katritzky, L. Jiang and P.J. Steel, J. Org. Chem., 59, 4551 (1994); https://doi.org/10.1021/jo00095a034
- A. Fuerstner, H. Weintritt and A. Hupperts, J. Org. Chem., 60, 6637 (1995); https://doi.org/10.1021/jo00125a068
- V.F. Ferreira, M.C.B.V. De Souza, A.C. Cunha, L.O.R. Pereira and M.L.G. Ferreira, Org. Prep. Proced. Int., 33, 411 (2001); https://doi.org/10.1080/00304940109356613
- I. Elghamry, Synth. Commun., 32, 897 (2002); https://doi.org/10.1081/SCC-120002701
- P.K. Chiu and M.P. Sammes, Tetrahedron, 46, 3439 (1990); https://doi.org/10.1016/S0040-4020(01)81514-3
- K. Aghapoor, F. Mohsenzadeh, H.R. Darabi, H. Sayahi and Y. Balavar, Res. Chem. Intermed., 42, 407 (2016); https://doi.org/10.1007/s11164-015-2026-1
- H. Huang, L. Tang, J. Cai and G.-J. Deng, RSC Adv., 6, 7011 (2016); https://doi.org/10.1039/C5RA24006A
- N.K. Jain, C.S. Patil, R.E. Kartasasmita, M. Decker, J. Lehmann and S.K. Kulkarni, Drgu Dev. Res., 61, 66 (2004); https://doi.org/10.1002/ddr.10337
- P. Helissey, C. Bailly, J.N. Vishwakarma, C. Auclair, M.J. Waring and S. Giorgi Renault, Anticancer Drug Des., 11, 527 (1996).
- M. Tercel, S.M. Stribbling, H. Sheppard, B.G. Siim, K. Wu, S.M. Pullen, K.J. Botting, W.R. Wilson and W.A. Denny, J. Med. Chem., 46, 2132 (2003); https://doi.org/10.1021/jm020526p
- P.G. Baraldi, G. Balboni, B. Cacciari, A. Guiotto, S. Manfredini, R. Romagnoli, G. Spalluto, D.E. Thurston, P.W. Howard, N. Bianchi, C. Rutigliano, C. Mischiati and R. Gambari, J. Med. Chem., 42, 5131 (1999); https://doi.org/10.1021/jm991033w
- P.G. Baraldi, G. Balboni, M.G. Pavani, G. Spalluto, M.A. Tabrizi, E.D. Clercq, J. Balzarini, T. Bando, H. Sugiyama and R. Romagnoli, J. Med. Chem., 44, 2536 (2001); https://doi.org/10.1021/jm0108404
References
C.T. Walsh, S. Garneau Tsodikova and A.R. Howard Jones, Nat. Prod. Rep., 23, 517 (2006); https://doi.org/10.1039/b605245m
D. Tzankova, S. Vladimirova, L. Peikova and M. Georgieva, J. Chem. Technol. Metall., 53, 451 (2018).
H. Hoffmann and T. Lindel, Synthesis, 1753 (2003); https://doi.org/10.1055/s-2003-41005
J.W. Huffman, Curr. Med. Chem., 6, 705 (1999).
A. Hall, S. Atkinson, S.H. Brown, I.P. Chessell, A. Chowdhury, G.M.P. Giblin, P. Goldsmith, M.P. Healy, K.S. Jandu, M.R. Johnson, A.D. Michel, A. Naylor and J.A. Sweeting, Bioorg. Med. Chem. Lett., 17, 1200 (2007); https://doi.org/10.1016/j.bmcl.2006.12.021
R.B. Thompson, FASEB J., 15, 1671 (2001); https://doi.org/10.1096/fj.01-0024lsf
D. Tejeswararao, J. Chil. Chem. Soc., 61, 2843 (2016); https://doi.org/10.4067/S0717-97072016000100018
P. Plitt, D.E. Gross, M.V. Lynch and J.L. Sessler, Chem. Eur. J., 13, 1374 (2007); https://doi.org/10.1002/chem.200601514
K. Kumar, S.S. More, S. Goyal, M. Gangar, G.L. Khatik, R.K. Rawal and V.A. Nair, Tetrahedron Lett., 57, 2315 (2016);
https://doi.org/10.1016/j.tetlet.2016.04.056 10. K. Ogawa and R.C. Rasmussen, J. Org. Chem., 68, 2921 (2003); https://doi.org/10.1021/jo034078k
D.W. Yoon, H. Hwang and C.H. Lee, Angew. Chem. Int. Ed., 41, 1757 (2002); https://doi.org/10.1002/1521-3773(20020517)41:10<1757::AIDANIE1757>3.0.CO;2-0
C.F. Lee, L.M. Yang, T.Y. Hwu, A.S. Feng, J.C. Tseng and T.Y. Luh, J. Am. Chem. Soc., 122, 4992 (2000); https://doi.org/10.1021/ja0004736
R.W. Burli, D. McMinn, J.A. Kaizerman, W. Hu, Y. Ge, Q. Pack, V. Jiang, M. Gross, M. Garcia, R. Tanaka and H.E. Moser, Bioorg. Med. Chem. Lett., 14, 1253 (2004); https://doi.org/10.1016/j.bmcl.2003.12.042
R.W. Burli, P. Jones, D. McMinn, Q. Le, J.X. Duan, J.A. Kaizerman, S. Difuntorum and H.E. Moser, Bioorg. Med. Chem. Lett., 14, 1259 (2004); https://doi.org/10.1016/j.bmcl.2003.12.043
M. Del Poeta, W.A. Schell, C.C. Dykstra, S. Jones, R.R. Tidwell, A. Czarny, M. Bajic, M. Bajic, A. Kumar, D. Boykin and J.R. Perfect, Antimicrob. Agents Chemother., 42, 2495 (1998); https://doi.org/10.1128/AAC.42.10.2495
E. Toja, D. Selva and P. Schiatti, J. Med. Chem., 27, 610 (1984); https://doi.org/10.1021/jm00371a010
V.J. Demopoulos and E. Rekka, J. Pharm. Sci., 84, 79 (1995); https://doi.org/10.1002/jps.2600840119
A.S. Girgis, J. Stawinski, N.S. Ismail and H. Farag, Eur. J. Med. Chem., 47, 312 (2012); https://doi.org/10.1016/j.ejmech.2011.10.058
J. Lehuede, B. Fauconneau, L. Barrier, M. Ourakow, A. Piriou and J.M. Vierfond, Eur. J. Med. Chem., 34, 991 (1999); https://doi.org/10.1016/S0223-5234(99)00111-7
R. Chesworth, M.D. Wessel, L. Heyden, F.M. Mangano, M. Zawistoski, L. Gegnas, D. Galluzzo, B. Lefker, K.O. Cameron, J. Tickner, B. Lu, T.A. Castleberry, D.N. Petersen, A. Brault, P. Perry, O. Ng, T.A. Owen, L. Pan, H.Z. Ke, T.A. Brown, D.D. Thompson and P. DaSilva Jardine, Bioorg. Med. Chem. Lett., 15, 5562 (2005); https://doi.org/10.1016/j.bmcl.2005.08.010
K. Liu, H. Lu, L. Hou, Z. Qi, C. Teixeira, F. Barbault, B.-T. Fan, S. Liu, S. Jiang and L. Xie, J. Med. Chem., 51, 7843 (2008); https://doi.org/10.1021/jm800869t
V.F. Ferreira, M.C.B.V. de Souza, A.C. Cunha, L.O.R. Pereira and M.L.G. Ferreira, Org. Prep. Proced. Int., 33, 411 (2001); https://doi.org/10.1080/00304940109356613
T.L.J. Gilchrist, Chem. Soc. Perkin Trans. I, 615 (1998); https://doi.org/10.1039/a704493c
R.K. Dieter and H. Yu, Org. Lett., 2, 2283 (2000); https://doi.org/10.1021/ol006050q
N. Iwasawa, K. Maeyama and M. Saitou, J. Am. Chem. Soc., 119, 1486 (1997); https://doi.org/10.1021/ja962173n
A. Katritzky, L. Jiang and P.J. Steel, J. Org. Chem., 59, 4551 (1994); https://doi.org/10.1021/jo00095a034
A. Fuerstner, H. Weintritt and A. Hupperts, J. Org. Chem., 60, 6637 (1995); https://doi.org/10.1021/jo00125a068
V.F. Ferreira, M.C.B.V. De Souza, A.C. Cunha, L.O.R. Pereira and M.L.G. Ferreira, Org. Prep. Proced. Int., 33, 411 (2001); https://doi.org/10.1080/00304940109356613
I. Elghamry, Synth. Commun., 32, 897 (2002); https://doi.org/10.1081/SCC-120002701
P.K. Chiu and M.P. Sammes, Tetrahedron, 46, 3439 (1990); https://doi.org/10.1016/S0040-4020(01)81514-3
K. Aghapoor, F. Mohsenzadeh, H.R. Darabi, H. Sayahi and Y. Balavar, Res. Chem. Intermed., 42, 407 (2016); https://doi.org/10.1007/s11164-015-2026-1
H. Huang, L. Tang, J. Cai and G.-J. Deng, RSC Adv., 6, 7011 (2016); https://doi.org/10.1039/C5RA24006A
N.K. Jain, C.S. Patil, R.E. Kartasasmita, M. Decker, J. Lehmann and S.K. Kulkarni, Drgu Dev. Res., 61, 66 (2004); https://doi.org/10.1002/ddr.10337
P. Helissey, C. Bailly, J.N. Vishwakarma, C. Auclair, M.J. Waring and S. Giorgi Renault, Anticancer Drug Des., 11, 527 (1996).
M. Tercel, S.M. Stribbling, H. Sheppard, B.G. Siim, K. Wu, S.M. Pullen, K.J. Botting, W.R. Wilson and W.A. Denny, J. Med. Chem., 46, 2132 (2003); https://doi.org/10.1021/jm020526p
P.G. Baraldi, G. Balboni, B. Cacciari, A. Guiotto, S. Manfredini, R. Romagnoli, G. Spalluto, D.E. Thurston, P.W. Howard, N. Bianchi, C. Rutigliano, C. Mischiati and R. Gambari, J. Med. Chem., 42, 5131 (1999); https://doi.org/10.1021/jm991033w
P.G. Baraldi, G. Balboni, M.G. Pavani, G. Spalluto, M.A. Tabrizi, E.D. Clercq, J. Balzarini, T. Bando, H. Sugiyama and R. Romagnoli, J. Med. Chem., 44, 2536 (2001); https://doi.org/10.1021/jm0108404