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Copyright (c) 2014 Y.N. Mabkhot1, N.N.E. El-Sayed1, F. Alatibi1, A. Barakat1, H.A. Ghabbour3, H-K. Fun3
This work is licensed under a Creative Commons Attribution 4.0 International License.
Synthesis, Characterization and X-Ray Crystal Structure of 3-Methyl-4-oxo-7-phenyl-4,7-dihydrothieno[2,3-b]pyridine-2-carboxyxlic Acid Ethyl Ester
Corresponding Author(s) : Y.N. Mabkhot1
Asian Journal of Chemistry,
Vol. 26 No. 24 (2014)
Abstract
Synthesis of 3-methyl-4-oxo-7-phenyl-4,7-dihydrothieno[2,3-b]pyridine-2-carboxylic acid ethyl ester (3) is described. The structure of the title compound 3 is confirmed by NMR, FT-IR, MS, CHN microanalysis, and X-ray crystallography. Compound 3 is a useful, functionalized pyrido thiophene derivative that can be transformed to novel heteroaromatics of potential pharmacological activities.
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- H.M. Hassneen and T.A. Abdallah, Molecules, 8, 333 (2003).
- S. Bondock, W. Fadaly and M.A. Metwally, Eur. J. Med. Chem., 45, 3692 (2010).
- Y.N. Mabkhot, A.M. Al-Majid and A.S. Alamary, Molecules, 16, 7706 (2011).
- K.M. Dawood, A.M. Farag and Z.E. Kandeel, J. Chem. Res. (S), 88 (1999).
- P. Lue and J.V. Greenhill, Adv. Heterocycl. Chem., 67, 207 (1996).
- P.G. Baraldi, A. Barco, S. Benetti, G.P. Pollini and D. Simoni, Synthesis, 857 (1987).
- A.M. Rolim Bernardino, L.C. da Silva Pinheiro, C.R. Rodrigues, N.I. Loureiro, H.C. Castro, A. Lanfredi-Rangel, J. Sabatini-Lopes, J.C. Borges, J.M. Carvalho, G.A. Romeiro, V.F. Ferreira, I.C.P.P. Frugulhetti and M.A. Vannier-Santos, Bioorg. Med. Chem., 14, 5765 (2006).
- S.A. Al-Trawneh, M.M. El-Abadelah, J.A. Zahra, S.A. Al-Taweel, F. Zani, M. Incerti, A. Cavazzoni and P. Vicini, Bioorg. Med. Chem., 19, 2541 (2011).
- J.P. Wu, R. Fleck, J. Brickwood, A. Capolino, K. Catron, Z. Chen, C. Cywin, J. Emeigh, M. Foerst, J. Ginn, M. Hrapchak, E. Hickey, M.-H. Hao, M. Kashem, J. Li, W. Liu, T. Morwick, R. Nelson, D. Marshall, L. Martin, P. Nemoto, I. Potocki, M. Liuzzi, G.W. Peet, E. Scouten, D. Stefany, M. Turner, S. Weldon, C. Zimmitti, D. Spero and T.A. Kelly, Bioorg. Med. Chem. Lett., 19, 5547 (2009).
- J.W. Lockman, M.D. Reeder, K. Suzuki, K. Ostanin, R. Hoff, L. Bhoite, H. Austin, V. Baichwal and J. Adam Willardsen, Bioorg. Med. Chem. Lett., 20, 2283 (2010).
- M.E. Schnute, D.J. Anderson, R.J. Brideau, F.L. Ciske, S.A. Collier, M.M. Cudahy, M.J. Eggen, M.J. Genin, T.A. Hopkins, T.M. Judge, E.J. Kim, M.L. Knechtel, S.K. Nair, J.A. Nieman, N.L. Oien, A. Scott, S.P. Tanis, V.A. Vaillancourt, M.W. Wathen and J.L. Wieber, Bioorg. Med. Chem. Lett., 17, 3349 (2007).
- L.C.S. Pinheiro, J.C. Borges, C.D. Oliveira, V.F. Ferreira and G.A. Romerio, ARKIVOC, 77 (2008).
- H. Liu, Y. Li, X.Y. Wang, B. Wang, H.Y. He, J.Y. Liu, M.L. Xiang, J. He, X.H. Wu and L. Yang, Bioorg. Med. Chem. Lett., 23, 2349 (2013).
- I. Adachi, T. Yamamori, Y. Hiramatsu, K. Sakai, S. Mihara, M. Kawakami, M. Masui, O. Uno and M. Ueda, Chem. Pharm. Bull. (Tokyo), 36, 4389 (1988).
- K. Saito, A. Nakao, T. Shinozuka, K. Shimada, S. Matsui, K. Oizumi, K. Yano, K. Ohata, D. Nakai, Y. Nagai and S. Naito, Bioorg. Med. Chem., 21, 1628 (2013).
- M.M. El-Abadelah, S.S. Sabri, H.A. Al-Ashqar, P. Mion, J. Bompart and M.É. Calas, Phosphorus Sulfur Silicon Relat. Elem., 134/135, 21 (1998).
- E.R. Bacon and S.J. Daum, Heterocycl. Chem., 28, 1953 (1991).
- Y.N. Mabkhoot, Molecules, 14, 1904 (2009).
- Y.N. Mabkhoot, Molecules, 15, 3329 (2010).
- Y.N. Mabkhot, N. abd Elshafy Kheder and A.M. Al-Majid, Molecules, 15, 9418 (2010).
- G.M. Sheldrick, Acta Crystallogr., 64A, 112 (2008).
- A.L. Spek, Acta Crystallogr., 65D, 148 (2009).
References
H.M. Hassneen and T.A. Abdallah, Molecules, 8, 333 (2003).
S. Bondock, W. Fadaly and M.A. Metwally, Eur. J. Med. Chem., 45, 3692 (2010).
Y.N. Mabkhot, A.M. Al-Majid and A.S. Alamary, Molecules, 16, 7706 (2011).
K.M. Dawood, A.M. Farag and Z.E. Kandeel, J. Chem. Res. (S), 88 (1999).
P. Lue and J.V. Greenhill, Adv. Heterocycl. Chem., 67, 207 (1996).
P.G. Baraldi, A. Barco, S. Benetti, G.P. Pollini and D. Simoni, Synthesis, 857 (1987).
A.M. Rolim Bernardino, L.C. da Silva Pinheiro, C.R. Rodrigues, N.I. Loureiro, H.C. Castro, A. Lanfredi-Rangel, J. Sabatini-Lopes, J.C. Borges, J.M. Carvalho, G.A. Romeiro, V.F. Ferreira, I.C.P.P. Frugulhetti and M.A. Vannier-Santos, Bioorg. Med. Chem., 14, 5765 (2006).
S.A. Al-Trawneh, M.M. El-Abadelah, J.A. Zahra, S.A. Al-Taweel, F. Zani, M. Incerti, A. Cavazzoni and P. Vicini, Bioorg. Med. Chem., 19, 2541 (2011).
J.P. Wu, R. Fleck, J. Brickwood, A. Capolino, K. Catron, Z. Chen, C. Cywin, J. Emeigh, M. Foerst, J. Ginn, M. Hrapchak, E. Hickey, M.-H. Hao, M. Kashem, J. Li, W. Liu, T. Morwick, R. Nelson, D. Marshall, L. Martin, P. Nemoto, I. Potocki, M. Liuzzi, G.W. Peet, E. Scouten, D. Stefany, M. Turner, S. Weldon, C. Zimmitti, D. Spero and T.A. Kelly, Bioorg. Med. Chem. Lett., 19, 5547 (2009).
J.W. Lockman, M.D. Reeder, K. Suzuki, K. Ostanin, R. Hoff, L. Bhoite, H. Austin, V. Baichwal and J. Adam Willardsen, Bioorg. Med. Chem. Lett., 20, 2283 (2010).
M.E. Schnute, D.J. Anderson, R.J. Brideau, F.L. Ciske, S.A. Collier, M.M. Cudahy, M.J. Eggen, M.J. Genin, T.A. Hopkins, T.M. Judge, E.J. Kim, M.L. Knechtel, S.K. Nair, J.A. Nieman, N.L. Oien, A. Scott, S.P. Tanis, V.A. Vaillancourt, M.W. Wathen and J.L. Wieber, Bioorg. Med. Chem. Lett., 17, 3349 (2007).
L.C.S. Pinheiro, J.C. Borges, C.D. Oliveira, V.F. Ferreira and G.A. Romerio, ARKIVOC, 77 (2008).
H. Liu, Y. Li, X.Y. Wang, B. Wang, H.Y. He, J.Y. Liu, M.L. Xiang, J. He, X.H. Wu and L. Yang, Bioorg. Med. Chem. Lett., 23, 2349 (2013).
I. Adachi, T. Yamamori, Y. Hiramatsu, K. Sakai, S. Mihara, M. Kawakami, M. Masui, O. Uno and M. Ueda, Chem. Pharm. Bull. (Tokyo), 36, 4389 (1988).
K. Saito, A. Nakao, T. Shinozuka, K. Shimada, S. Matsui, K. Oizumi, K. Yano, K. Ohata, D. Nakai, Y. Nagai and S. Naito, Bioorg. Med. Chem., 21, 1628 (2013).
M.M. El-Abadelah, S.S. Sabri, H.A. Al-Ashqar, P. Mion, J. Bompart and M.É. Calas, Phosphorus Sulfur Silicon Relat. Elem., 134/135, 21 (1998).
E.R. Bacon and S.J. Daum, Heterocycl. Chem., 28, 1953 (1991).
Y.N. Mabkhoot, Molecules, 14, 1904 (2009).
Y.N. Mabkhoot, Molecules, 15, 3329 (2010).
Y.N. Mabkhot, N. abd Elshafy Kheder and A.M. Al-Majid, Molecules, 15, 9418 (2010).
G.M. Sheldrick, Acta Crystallogr., 64A, 112 (2008).
A.L. Spek, Acta Crystallogr., 65D, 148 (2009).