Copyright (c) 2014 AJC
This work is licensed under a Creative Commons Attribution 4.0 International License.
Synthesis and Reactions of Some New Heterocyclic Compounds
Corresponding Author(s) : Yahia N. Mabkhot
Asian Journal of Chemistry,
Vol. 26 No. 19 (2014): Vol 26 Issue 19
Abstract
Synthesis and reactions of some new heterocyclic compounds containing a thieno[2,3-b]thiophene e.g., bis-thieno[2,3-b]thiophene derivatives 3a-d, 6 and 7 are described. The structures of all newly synthesized compounds have been elucidated by 1H, 13C NMR, GCMS and IR spectrometry. These compounds represent a new class of nitrogen and sulfur containing heterocycles that should also be of interest as new materials.
Keywords
Download Citation
Endnote/Zotero/Mendeley (RIS)BibTeX
- D. Shen, M. Shu and K.T. Chapman, Org. Lett., 2, 2789 (2000); doi:10.1021/ol006197h.
- S. Dadiboyena, E.J. Valente and A.T. Hamme II, Tetrahedron Lett., 50, 291 (2009); doi:10.1016/j.tetlet.2008.10.145.
- Y.N. Mabkhot, A.M. Al-Majid and A.S. Alamary, Molecules, 16, 7706 (2011); doi:10.3390/molecules16097706.
- M.D. Carrion, L.C. Lopez Cara, E.V. Camacho, M. Tapias, G. Escames, D. Acuña-Castroviejo, A. Espinosa, M.A. Gallo and A. Entrena, Eur. J. Med. Chem., 43, 2579 (2008); doi:10.1016/j.ejmech.2008.01.014.
- N. Gokhan-Kelekçi, S. Koyunoglu, S. Yabanoglu, K. Yelekçi, Ö. Özgen, G. Uçar, K. Erol, E. Kendi and A. Yeşilada, Bioorg. Med. Chem., 17, 675 (2009); doi:10.1016/j.bmc.2008.11.068.
- X.H. Liu, L.P. Zhi, B.A. Song and H.L. Xu, Chem. Res., 24, 454 (2008).
- M. Abid, A.R. Bhat, F. Athar and A. Azam, Eur. J. Med. Chem., 44, 417 (2009); doi:10.1016/j.ejmech.2007.10.032.
- A.M. Farag, A.S. Mayhoub, S.E. Barakat and A.H. Bayomi, Bioorg. Med. Chem., 16, 881 (2008); doi:10.1016/j.bmc.2007.10.015.
- A.M. Farag, A.M. Mayhoub, A.S. Barakat and S.E. Bayomi, Bioorg. Med. Chem., 16, 4569 (2008); doi:10.1016/j.bmc.2008.02.043.
- Y. Hui, R. Ptak, R. Paulman, M. Pallansch and C.W.T. Chang, Tetrahedron Lett., 43, 9255 (2002); doi:10.1016/S0040-4039(02)02248-7.
- J.K. Chakrabarti, L. Horsman, T.M. Hotten, I.A. Pullar, D.E. Tupper and F.C. Wright, J. Med. Chem., 23, 878 (1980); doi:10.1021/jm00182a013.
- V.J. Ram, H.K. Pandey and A.J. Vlietinck, J. Heterocycl. Chem., 18, 55 (1981); doi:10.1002/jhet.5570180111.
- I. Jarak, M. Kralj, I. Piantanida, L. Suman, M. Zinic, K. Pavelic and G. Karminski-Zamola, Bioorg. Med. Chem., 14, 2859 (2006); doi:10.1016/j.bmc.2005.12.004.
- D. Peters, A.B. Hornfeldt and S. Gronowitz, J. Heterocycl. Chem., 27, 2165 (1990); doi:10.1002/jhet.5570270756.
- S. Kukolja, S.E. Draheim, B.J. Graves, D.C. Hunden, J.L. Pfeil, R.D.G. Cooper, J.L. Ott and F.T. Counter, J. Med. Chem., 28, 1896 (1985); doi:10.1021/jm00150a023.
- J.D. Prugh, G.D. Hartman, P.J. Mallorga, B.M. McKeever, S.R. Michelson, M.A. Murcko, H. Schwam, R.L. Smith, J.M. Sondey, J.P. Springer and M.F. Surgrue, J. Med. Chem., 34, 1805 (1991); doi:10.1021/jm00110a008.
- G.D. Hartman and P.A. Ansdale, U.S. Patent 4,806,562, 21 February (1989).
- V.P. Litvinov, Russ. Chem. Rev., 74, 217 (2005); doi:10.1070/RC2005v074n03ABEH000889.
- M.C. Gather, M. Heeney, W. Zhang, K.S. Whitehead, D.D.C. Bradley, I. McCulloch and A.J. Campbell, Chem. Commun., 1079 (2008); doi:10.1039/b716510b.
- M. He, J. Li, M.L. Sorensen, F. Zhang, R.R. Hancock, H.H. Fong, V.A. Pozdin, D. Smilgies and G.G. Malliaras, J. Am. Chem. Soc., 131, 11930 (2009); doi:10.1021/ja903895s.
- A.G. Griffin and T.R. Britt, J. Am. Chem. Soc., 103, 4957 (1981); doi:10.1021/ja00406a056.
- G. Galli, M. Laus and A.S. Angeloni, Makromol. Chem., 187, 289 (1986); doi:10.1002/macp.1986.021870206.
- H. Finkelmann, Angew. Chem. Int. Ed. Engl., 26, 816 (1987); doi:10.1002/anie.198708161.
- C. Aguilera, M. Parra and G. Fuentes, Z. Naturforsch, 53b, 367 (1998).
- D. Braun, R. Langendorf and I. Vitrigens, J. Prakt. Chem., 341, 128 (1999); doi:10.1002/(SICI)1521-3897(199902)341:2<128::AID-PRAC128>3.0.CO;2-M.
- E.J. Ariens, Drug Design, Academic Press: New York, NY, USA (1971).
- A.H.M. Elwahy and A.A. Abbas, Synth. Commun., 30, 2903 (2000); doi:10.1080/00397910008087441.
- A.A. Abbas, M.A.A. Elneairy and Y.N. Mabkhot, J. Chem. Res., 2001, 124 (2001); doi:10.3184/030823401103169388.
- M.A.A. Elneairy, A.A. Abbas and Y.N. Mabkhout, Phosphorus Sulfur Silicon Rel. Elem., 178, 1747 (2003); doi:10.1080/10426500307823.
- A.A. Abbas and N.M. Rateb, Phosphorus Sulfur Silicon Rel. Elem., 180, 497 (2005); doi:10.1080/104265090517226.
- A.A. Elassar and A.A. El-Khair, Tetrahedron, 59, 8463 (2003); doi:10.1016/S0040-4020(03)01201-8.
- Y. Nasser Mabkhot, A. Barakat, A.M. Al-Majid, Z. Al-Othman and A.S. Alamary, Int. J. Mol. Sci., 12, 7824 (2011); doi:10.3390/ijms12117824.
- F. Al-Omran, N. Al-Awadi, A.A. El-Khair and M.H. Elnagdi, Org. Prep. Proced. Int., 29, 285 (1997); doi:10.1080/00304949709355198.
References
D. Shen, M. Shu and K.T. Chapman, Org. Lett., 2, 2789 (2000); doi:10.1021/ol006197h.
S. Dadiboyena, E.J. Valente and A.T. Hamme II, Tetrahedron Lett., 50, 291 (2009); doi:10.1016/j.tetlet.2008.10.145.
Y.N. Mabkhot, A.M. Al-Majid and A.S. Alamary, Molecules, 16, 7706 (2011); doi:10.3390/molecules16097706.
M.D. Carrion, L.C. Lopez Cara, E.V. Camacho, M. Tapias, G. Escames, D. Acuña-Castroviejo, A. Espinosa, M.A. Gallo and A. Entrena, Eur. J. Med. Chem., 43, 2579 (2008); doi:10.1016/j.ejmech.2008.01.014.
N. Gokhan-Kelekçi, S. Koyunoglu, S. Yabanoglu, K. Yelekçi, Ö. Özgen, G. Uçar, K. Erol, E. Kendi and A. Yeşilada, Bioorg. Med. Chem., 17, 675 (2009); doi:10.1016/j.bmc.2008.11.068.
X.H. Liu, L.P. Zhi, B.A. Song and H.L. Xu, Chem. Res., 24, 454 (2008).
M. Abid, A.R. Bhat, F. Athar and A. Azam, Eur. J. Med. Chem., 44, 417 (2009); doi:10.1016/j.ejmech.2007.10.032.
A.M. Farag, A.S. Mayhoub, S.E. Barakat and A.H. Bayomi, Bioorg. Med. Chem., 16, 881 (2008); doi:10.1016/j.bmc.2007.10.015.
A.M. Farag, A.M. Mayhoub, A.S. Barakat and S.E. Bayomi, Bioorg. Med. Chem., 16, 4569 (2008); doi:10.1016/j.bmc.2008.02.043.
Y. Hui, R. Ptak, R. Paulman, M. Pallansch and C.W.T. Chang, Tetrahedron Lett., 43, 9255 (2002); doi:10.1016/S0040-4039(02)02248-7.
J.K. Chakrabarti, L. Horsman, T.M. Hotten, I.A. Pullar, D.E. Tupper and F.C. Wright, J. Med. Chem., 23, 878 (1980); doi:10.1021/jm00182a013.
V.J. Ram, H.K. Pandey and A.J. Vlietinck, J. Heterocycl. Chem., 18, 55 (1981); doi:10.1002/jhet.5570180111.
I. Jarak, M. Kralj, I. Piantanida, L. Suman, M. Zinic, K. Pavelic and G. Karminski-Zamola, Bioorg. Med. Chem., 14, 2859 (2006); doi:10.1016/j.bmc.2005.12.004.
D. Peters, A.B. Hornfeldt and S. Gronowitz, J. Heterocycl. Chem., 27, 2165 (1990); doi:10.1002/jhet.5570270756.
S. Kukolja, S.E. Draheim, B.J. Graves, D.C. Hunden, J.L. Pfeil, R.D.G. Cooper, J.L. Ott and F.T. Counter, J. Med. Chem., 28, 1896 (1985); doi:10.1021/jm00150a023.
J.D. Prugh, G.D. Hartman, P.J. Mallorga, B.M. McKeever, S.R. Michelson, M.A. Murcko, H. Schwam, R.L. Smith, J.M. Sondey, J.P. Springer and M.F. Surgrue, J. Med. Chem., 34, 1805 (1991); doi:10.1021/jm00110a008.
G.D. Hartman and P.A. Ansdale, U.S. Patent 4,806,562, 21 February (1989).
V.P. Litvinov, Russ. Chem. Rev., 74, 217 (2005); doi:10.1070/RC2005v074n03ABEH000889.
M.C. Gather, M. Heeney, W. Zhang, K.S. Whitehead, D.D.C. Bradley, I. McCulloch and A.J. Campbell, Chem. Commun., 1079 (2008); doi:10.1039/b716510b.
M. He, J. Li, M.L. Sorensen, F. Zhang, R.R. Hancock, H.H. Fong, V.A. Pozdin, D. Smilgies and G.G. Malliaras, J. Am. Chem. Soc., 131, 11930 (2009); doi:10.1021/ja903895s.
A.G. Griffin and T.R. Britt, J. Am. Chem. Soc., 103, 4957 (1981); doi:10.1021/ja00406a056.
G. Galli, M. Laus and A.S. Angeloni, Makromol. Chem., 187, 289 (1986); doi:10.1002/macp.1986.021870206.
H. Finkelmann, Angew. Chem. Int. Ed. Engl., 26, 816 (1987); doi:10.1002/anie.198708161.
C. Aguilera, M. Parra and G. Fuentes, Z. Naturforsch, 53b, 367 (1998).
D. Braun, R. Langendorf and I. Vitrigens, J. Prakt. Chem., 341, 128 (1999); doi:10.1002/(SICI)1521-3897(199902)341:2<128::AID-PRAC128>3.0.CO;2-M.
E.J. Ariens, Drug Design, Academic Press: New York, NY, USA (1971).
A.H.M. Elwahy and A.A. Abbas, Synth. Commun., 30, 2903 (2000); doi:10.1080/00397910008087441.
A.A. Abbas, M.A.A. Elneairy and Y.N. Mabkhot, J. Chem. Res., 2001, 124 (2001); doi:10.3184/030823401103169388.
M.A.A. Elneairy, A.A. Abbas and Y.N. Mabkhout, Phosphorus Sulfur Silicon Rel. Elem., 178, 1747 (2003); doi:10.1080/10426500307823.
A.A. Abbas and N.M. Rateb, Phosphorus Sulfur Silicon Rel. Elem., 180, 497 (2005); doi:10.1080/104265090517226.
A.A. Elassar and A.A. El-Khair, Tetrahedron, 59, 8463 (2003); doi:10.1016/S0040-4020(03)01201-8.
Y. Nasser Mabkhot, A. Barakat, A.M. Al-Majid, Z. Al-Othman and A.S. Alamary, Int. J. Mol. Sci., 12, 7824 (2011); doi:10.3390/ijms12117824.
F. Al-Omran, N. Al-Awadi, A.A. El-Khair and M.H. Elnagdi, Org. Prep. Proced. Int., 29, 285 (1997); doi:10.1080/00304949709355198.