Influence of solvent and substituents on the reaction of N-alkylthioacetamides with dimethyl acetylenedicarboxylate: Synthesis of functionalized thiophenes containing an exocyclic double bond / Obydennov K.L., Klimareva E.L., Kosterina M.F., Slepukhin P.A., Morzherin Y.Y. // Tetrahedron Letters. - 2013. - V. 54, l. 36. - P. 4876-4879.

ISSN:
00404039
Type:
Article
Abstract:
The reaction of thioacetamides with dimethyl acetylenedicarboxylate affords 3-oxothien-2-ylidene or 4-oxothiazol-2,5-ylidene derivatives based on the structure of the thioacetamides and the solvent employed. The structural features of the 3-oxothien-2-ylidenes are discussed. © 2013 Elsevier Ltd. All rights reserved.
Author keywords:
Acetylenedicarboxylate; Exocyclic double bond; Thiazole; Thioacetamide; Thiophene
Index keywords:
3 oxothien 2 ylidene derivative; 4 oxothiazol 2,5 ylidene; acetylenedicarboxylic acid dimethyl ester; n alkylthioacetamide derivative; thiazole derivative; thioacetamide derivative; thiophene derivati
DOI:
10.1016/j.tetlet.2013.06.127
Смотреть в Scopus:
https://www.scopus.com/inward/record.uri?eid=2-s2.0-84881154876&doi=10.1016%2fj.tetlet.2013.06.127&partnerID=40&md5=d07f1179ff87855269c75fe116248bbe
Соавторы в МНС:
Другие поля
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Link https://www.scopus.com/inward/record.uri?eid=2-s2.0-84881154876&doi=10.1016%2fj.tetlet.2013.06.127&partnerID=40&md5=d07f1179ff87855269c75fe116248bbe
Affiliations Ural Federal University, Mira 19, Ekaterinburg 620002, Russian Federation; I. Postovsky Institute of Organic Synthesis, Kovalevskoy 22, Ekaterinburg 620090, Russian Federation
Author Keywords Acetylenedicarboxylate; Exocyclic double bond; Thiazole; Thioacetamide; Thiophene
Chemicals/CAS acetylenedicarboxylic acid dimethyl ester, 762-42-5
References Bren, V.A., Dubonosov, A.D., Minkin, V.I., Tsukanov, A.V., Gribanova, T.N., Shepelenko, E.N., Revinsky, Y.V., Rybalkin, V.P., (2007) J. Phys. Org. Chem., 20, pp. 917-928; Manzhos, S., Segawa, H., Yamashita, K., (2012) Chem. Phys. Lett., 527, pp. 51-56; Knieb, A., Gruner, M., Mayer, R., (1996) Monatsh. Chem., 127, pp. 1173-1187; Khmel'Nitskaya, E.Yu., Grigor'Ev, N.B., Ryabova, S.Yu., Trofimkin, Yu.I., Azimov, V.A., Granik, V.G., (2002) Chem. Heterocycl. Compd., 38, pp. 1357-1362; Takekuma, S.-I., Sonoda, K., Minematsu, T., Takekuma, H., (2008) Tetrahedron, 64, pp. 3802-3812; Marin, L., Van Mierloo, S., Zhang, Y., Robeyns, K., Champagne, B., Adriaensens, P., Lutsen, L., Maes, W., (2013) Tetrahedron, 69, p. 2260; Bromby, A.D., Jansonius, R.P., Sutherland, T.C., (2013) J. Org. Chem., 78, pp. 1612-1620; Kosterina, M.F., Morzherin, Yu.Yu., Tkachev, A.V., Rybalova, T.V., Gatilov, Yu.V., Bakulev, V.A., (2002) Russ. Chem. Bull., 51, p. 653; Danilkina, N.A., Mikhailov, L.E., Ivin, B.A., (2006) Russ. J. Org. Chem., 42, pp. 783-814; Britsun, V.N., Esipenko, A.N., Lozinskii, M.O., (2008) Chem. Heterocycl. Compd., 44, pp. 1429-1459; Obydennov, K.L., Kosterina, M.F., Klimareva, E.L., Bakulev, V.A., Morzherin, Yu.Yu., (2011) Russ. Chem. Bull., 5, pp. 1016-1018; http://www.ccdc.cam.ac.uk/data_request/cif, mailto:deposited@ccdc.cam.ac.uk The structure of compound 7a was deposited with the Cambridge Crystallographic Data Centre (No. CCDC 930944; or); Guo, Y., Yan, Y., Zhi, X., Yang, C., Hu, H., (2013) Bioorg. Med. Chem. Lett., pp. 3382-3384; Mérour, J.-Y., Chichereau, L., Desarbre, E., Gadonneix, P., (1996) Synthesis, pp. 519-524; Palacios, F., Alonso, C., Rubiales, G., Villegas, M., (2009) Tetrahedron, pp. 1119-1124; Palluotto, F., Campagna, F., Carotti, A., Ferappi, M., Rosato, A., Vitali II, C., (2002) Farmaco, pp. 63-69; Berseneva, V.S., Tkachev, A.V., Morzherin, Yu.Yu., Dehaen, W., Luyten, I., Toppet, S., Bakulev, V.A., (1998) J. Chem. Soc., Perkin Trans. 1, pp. 2133-2136
Correspondence Address Obydennov, K.L.; Ural Federal University, Mira 19, Ekaterinburg 620002, Russian Federation; email: k.l.obydennov@ustu.ru
CODEN TELEA
Language of Original Document English
Abbreviated Source Title Tetrahedron Lett.
Source Scopus