Abstract
3-Phenyl-2-(prop-2-en-1-ylsulfanyl)-5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidin-4(3H)-one reacted with 4-methoxyphenyltellurium trichloride in a regioselective manner to give angularly fused 1-{[dichloro(4-methoxyphenyl)-λ4-tellanyl]methyl}-4-oxo-5-phenyl-1,2,4,5,6,7,8,9-octahydrobenzo[4,5]thieno[3,2-e][1,3]thiazolo[3,2-a]pyrimidinium chloride. Electrophilic cyclization of 2-(prop-2-en-1-ylsulfanyl)- and 2-(2-methylprop-2-en-1-ylsulfanyl)-5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidin-4(3H)-ones with 4-methoxyphenyltellurium trichloride afforded linearly fused 3-{[dichloro(4-methoxyphenyl)-λ4-tellanyl]methyl}-2,3,6,7,8,9-hexahydro-5H-benzo[4,5]thieno[2,3-d][1,3]thiazolo[3,2-a]pyrimidin-5-one hydrochlorides. Regardless of the reactant ratio, the products were isolated as 1:1 complexes with 4-methoxyphenyltellurium trichloride.
Similar content being viewed by others
REFERENCES
Slivchuk, S.V., Brovarets, V.S., and Drach, B.S., Russ. J. Gen. Chem., 2008, vol. 78, p. 1210. https://doi.org/10.1134/S1070363208060194
Slivka, N.Yu., Gevaza, Yu.I., and Staninets, V.I., Chem. Heterocycl. Compd., 2004, vol. 40, p. 660. https://doi.org/10.1023/B:COHC.0000037323.22839.9f
Frolova, T.V., Slepuhin, P.A., and Kim, D.G., Chem. Heterocycl. Compd., 2011, vol. 47, p. 252. https://doi.org/10.1007/s10593-011-0751-y
Studzińska, R., Wróblewski, M., KarczmarskaWódzka, A., and Kołodziejska, R., Tetrahedron Lett., 2014, vol. 55, p. 1384. https://doi.org/10.1016/j.tetlet.2014.01.033
Bakhteeva, E.I., Kim, D.G., Dmitriev, M.V., and Krylova, Y.E., Russ. J. Org. Chem., 2019, vol. 55, p. 748. https://doi.org/10.1134/S1070428019060022
Zborovskii, Yu.L., Orysyk, V.V., Dobosh, A.A., Staninets, V.I., Pirozhenko, V.V., and Chernega, A.N., Chem. Heterocycl. Compd., 2003, vol. 39, p. 1099. https://doi.org/10.1023/B:COHC.0000003532.58469.cc
Orysyk, V.V., Zborovskii, Yu.L., Staninets, V.I., Dobosh, A.A., and Khripak, S.M., Chem. Heterocycl. Compd., 2003, vol. 39, p. 640. https://doi.org/10.1023/A:1025154317771
Wippich, P., Gütschow, M., and Leistner, S., Synthesis, 2000, vol. 2000, no. 5, p. 714. https://doi.org/10.1055/s-2000-6390
Vas’kevich, R.I., Khripak, S.M., Staninets, V.I., and Zborovskii, Yu.L., and Chernega, A.N., Russ. J. Org. Chem., 2000, vol. 36, p. 1061.
Vaskevich, R.I., Khripak, S.M., Staninets, V.I.. Zborovskij, Y.L., Nesterenko, A.M., and Pirozhenko, V.V., Ukr. Khim. Zh., 2000, vol. 66, p. 47.
Vas’kevich, A.I., Vas’kevich, R.I., Staninets, V.I., But, S.A., and Chernega, A.N., Russ. J. Org. Chem., 2007, vol. 43, p. 1526. https://doi.org/10.1134/S107042800710020X
Slivka, M., Krivovjaz, A., Slivka, M., and Lendel, V., Heterocycl. Commun., 2013, vol. 19, p. 189. https://doi.org/10.1515/hc-2013-0036
Bentya, A.V., Vas’kevich, R.I., Bol’but, A.V., Vovk, M.V., Staninets, V.I., Turov, A.V., and Rusanov, E.B., Russ. J. Org. Chem., 2008, vol. 44, p. 1362. https://doi.org/10.1134/S1070428008090194
Vas’kevich, R.I., Bentya, A.V., Turov, A.V., Rusanov, E.B., Staninets, V.I., and Vovk, M.V., Russ. J. Org. Chem., 2012, vol. 48, p. 713. https://doi.org/10.1134/S1070428012050144
Svaljavyn, O.V., Onysko, M.Y., Turov, A.V., Vlasenko, Y.G., and Lendel, V.G., Chem. Heterocycl. Compd., 2013, vol. 49, p. 491. https://doi.org/10.1007/s10593-013-1273-6
Onysko, M.Yu., Svalyavin, O.V., Turov, A.V., and Lendel, V.G., Chem. Heterocycl. Compd., 2008, vol. 44, p. 872. https://doi.org/10.1007/s10593-008-0123-4
Onisko, M.Yu., Svalyavin, O.V., and Lendel, V.G., Chem. Heterocycl. Compd., 2007, vol. 43, p. 496. https://doi.org/10.1007/s10593-007-0072-3
Kut, M., Onysko, M., and Lendel, V., J. Heterocycl. Chem., 2018, vol. 55, p. 888. https://doi.org/10.1002/jhet.3114
Kut, M., Onysko, M., and Lendel, V., Heterocycl. Commun., 2016, vol. 22, p. 347. https://doi.org/10.1515/hc-2016-0169
Kut, M., Fizer, M., Onysko, M., and Lendel, V., J. Heterocycl. Chem., 2018, vol. 55, p. 2284. https://doi.org/10.1002/jhet.3281
Khripak, S.M., Yakubets, V.I., Migalina, Yu.V., Koz’min, A.S., and Zefirov, N.S., Chem. Heterocycl. Compd., 1989, vol. 25, p. 347. https://doi.org/10.1007/BF00472400
Wippich, P., Hendreich, C., Gütschow, M., and Leistner, S., Synthesis, 1996, vol. 1996, no. 6, p. 741.
Kut, M., Onysko, M., and Lendel, V., Sci. Bull. Uzhhorod Univ., Ser. Chem., 2019, vol. 42, p. 63. https://doi.org/10.24144/2414-0260.2019.2.63-72
Kut, M., Onysko, M., and Lendel, V., Sci. Bull. Uzhhorod Univ., Ser. Chem., 2019, vol. 41, p. 86. https://doi.org/10.24144/2414-0260.2019.1.86-89
Kut, M., Onysko, M., and Lendel, V., Sci. Bull. Uzhhorod Univ., Ser. Chem., 2019, vol. 41, p. 90. https://doi.org/10.24144/2414-0260.2019.1.90-93
Dyachenko, I.V., Vas’kevich, R.I., and Vovk, M.V., Russ. J. Org. Chem., 2014, vol. 50, p. 263. https://doi.org/10.1134/S1070428014020201
Vas’kevich, A.I., Vas’kevich, R.I., Staninets, V.I., But, S.A., and Chernega, A.N., Russ. J. Org. Chem., 2007, vol. 43, p. 1526. https://doi.org/10.1134/S107042800710020X
Dyachenko, I.V., Vas’kevich, A.I., Vas’kevich, R.I., and Vovk, M.V., Russ. J. Org. Chem., 2014, vol. 50, p. 858. https://doi.org/10.1134/S1070428014060189
Bentya, A.V., Vas’kevich, R.I., Turov, A.V., Rusanov, E.B., Vovk, M.V., and Staninets, V.I., Russ. J. Org. Chem., 2011, vol. 47, p. 1066. https://doi.org/10.1134/S1070428011070165
Chertkov, V.A., Shestakova, A.K., and Davydov, D.V., Chem. Heterocycl. Compd., 2011, vol. 47, p. 45. https://doi.org/10.1007/s10593-011-0718-z
Furrer, J., Concepts Magn. Reson., Part A, 2012, vol. 40, p. 101. https://doi.org/10.1002/cmr.a.21232
Reichel, L. and Kirschbaum, E., Justus Liebigs Ann. Chem., 1936, vol. 523, p. 211. https://doi.org/10.1002/jlac.19365230113
Author information
Authors and Affiliations
Corresponding author
Ethics declarations
The authors declare the absence of conflict of interest.
Rights and permissions
About this article
Cite this article
Kut, M.M., Onysko, M.Y., Suikov, S.Y. et al. Regioselectivity of Intramolecular Electrophilic Cyclization of 2-(Alkenylsulfanyl)thieno[2,3-d]pyrimidin-4(3H)-ones with p-Methoxyphenyltellurium Trichloride. Russ J Org Chem 56, 1711–1715 (2020). https://doi.org/10.1134/S1070428020100061
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S1070428020100061
Keywords:
- electrophilic cyclization
- p-methoxyphenyltellurium trichloride
- regioselectivity
- 2-(prop-2-en-1-ylsulfanyl)-3-phenyl-5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidin-4(3H)-one
- 2-(alkenylsulfanyl)- 5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidin-4(3H)-ones
- 1-{[dichloro(4-methoxyphenyl)-λ4-tellanyl]methyl}-4-oxo-5-phenyl-1,2,4,5,6,7,8,9-octahydrobenzo[4,5]thieno[3,2-e][1,3]thiazolo[3,2-a]pyrimidinium chloride
- 3-{[dichloro(4-methoxyphenyl)-λ4-tellanyl]methyl}-2,3,6,7,8,9-hexahydro-5H-benzo[4,5]thieno[2,3-d][1,3]thiazolo[3,2-a]pyrimidin-5-one hydrochloride