The reaction of vicinal thieno[2,3-b]pyridine aminoamides with Lawesson’s reagent gave new condensed diazaphosphinine derivatives. The structure of the substituent at the amide nitrogen atom and the reagent ratio were found to affect the direction of this reaction.
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A. E. Abdel-Rahman, E. A. Bakhite, and E. A. Al-Taifi, J. Chin. Chem. Soc., 49, 223 (2002).
M. A. A. Elneairy, S. M. Eldin, F. A. Attaby, and A. K. K. El-Louh, Phosphorus, Sulfur Silicon Relat. Elem., 167, 289 (2000).
G. Wagner, S. Leistner, H. Vieweg, U. Krasselt and J. Prantz, Pharmazie, 48, 514 (1993).
G. Z. Zheng, P. Bhatia, J. Daanen, T. Kolasa, M. Patel, S. Latshaw, O. F. El Kouhen, R. Chang, M. E. Uchic, L. Miller, M. Nakane, S. G. Lehto, M. P. Honore, R. B. Moreland, J. D. Brioni, and A. O. Stewart, J. Med. Chem., 48, 7374 (2005).
E. A. Kaigorodova, V. K. Vasilin, A. A. Osipova, M. M. Lipunov, and G. D. Krapivin, Izv. VUZov. Khim. i Khim. Tekhnol., 47, 144 (2004).
T. A. Stroganova, A. V. Butin, V. K. Vasilin, T. A. Nevolina, and G. D. Krapivin, Synlett, 1106 (2007).
T. A. Stroganova, V. K. Vasilin, E. A. Zelenskaya, V. M. Red'kin, and G. D. Krapivin, Synthesis, 3088 (2008).
T. A. Stroganova and I. V. Malikov, Khim. Geterotsikl. Soedin., 1431 (2009). [Chem. Heterocycl. Compd., 45, 1149 (2009)].
J. M. Quintela, C. Peinador, C. Veiga, L. González, L. M. Botana, A. Alfonso, and R. Riguera, Bioorg. Med. Chem., 6, 1911 (1998).
E. A. Bakhite, A. G. Al-Schemi, and Y. Yamada, J. Heterocycl. Chem., 42, 1069 (2005).
E. A. Bakhite, A. E. Abdel-Rahman, and E. A. Al-Taifi, Phosphorus, Sulfur Silicon Relat. Elem., 179, 513 (2004).
C. Zhao, C. Tovar, X. Yin, Z. Xu, I. T. Todorov, L. T. Vassilev, and L. Chen, Bioorg. Med. Chem. Lett., 19, 319 (2009).
V. V. Dotsenko, S. G. Krivokolysko, and V. P. Litvinov, Khim. Geterotsikl. Soedin., 117 (2003). [Chem. Heterocycl. Compd., 39, 110 (2003)].
O. S. Mohamed, E. A. Al-Taifi, T. I. El-Emary, and E. A.-G. Bakhite, Phosphorus, Sulfur Silicon Relat. Elem., 182, 1061 (2007).
M. Yu. Yakovlev, O. B. Romanova, S. I. Grizik, A. V. Kadushkin, and V. G. Granik, Khim.-Farm. Zh., 31, No. 11, 44 (1997).
M. A. A. El-Neairy, Phosphorus, Sulfur Relat. Elem., 148, 189 (1999).
Abdel-Rahman, E. A. Bakhite, and E. A. Al-Taifi, J. Chin. Chem. Soc., 49, 223 (2002).
G. Wagner, U. Krasselt, and S. Leistner, Pharmazie, 46, 409 (1991).
M. Jesberger, T. P. Davis, and L. Barner, Synthesis, 1929 (2003).
B. S. Pedersen and S.-O. Lawesson, Tetrahedron, 35, 2433 (1979).
S. Scheibye, J. Kristensen, and S.-O. Lawesson, 35, 1339 (1979).
T. Ozturk, E. Ertas, and O. Mert, Chem. Rev., 107, 5210 (2007).
H. M. Moustafa, Phosphorus, Sulfur Silicon Relat. Elem., 178, 1397 (2003).
A. A. El-Barbary and S.-O. Lawesson, Tetrahedron, 37, 2641 (1981).
V. K. Vasilin, M. M. Lipunov, L. D. Konyushkin, and G. D. Krapivin, Khim. Geterotsikl. Soedin., 1582 (2006). [Chem. Heterocycl. Compd., 42, 1368 (2006)].
D. Yu. Kosulina, V. K. Vasilin, T. A. Stroganova, E. A. Sbitneva, A. V. Butin, and G. D. Krapivin, Khim. Geterotsikl. Soedin., 1380 (2009). [Chem. Heterocycl. Compd., 45, 1105 (2009)].
E. A. Kaigorodova, L. D. Konyushkin, S. N. Mikhailichenko, V. K. Vasilin, and V. G. Kul'nevich, Khim. Geterotsikl. Soedin., 1432 (1996). [Chem. Heterocycl. Compd., 32, 1234 (1996)].
G. M. Sheldrick, SHELXL-97: Program for the Solution of Crystal Structures, University of Göttingen (1997).
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1817-1825, November, 2012.
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Red’kin, V.M., Stroganova, T.A., Vasilin, V.K. et al. Reaction of vicinal thieno[2,3-b]pyridine aminoamides with Lawesson’s reagent. Chem Heterocycl Comp 48, 1701–1709 (2013). https://doi.org/10.1007/s10593-013-1196-2
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DOI: https://doi.org/10.1007/s10593-013-1196-2