Thiophenols Addition Reactions to Siliconcontaining Enynes and Enynones

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Abstract

As well as the cross-conjugated enynones, propynylidene derivatives of malonic ester and Meldrum’s acid that contain Me3Si, Et3Si and t-BuMe2Si groups, attach stereoselectively 4-methyl-, 4-methoxy- and 4-chlorothiophenol under conditions of base catalysis. In the process, there are sulfanilic compounds containing buta-1,3-diene and penta-1,4-dien-3-one fragments formed in high yields. In the thiylation products of the enyne derivatives of malonic ester and Meldrum’s acid, Me3Si, Et3Si and t-BuMe2Si groups are retained; desilylation occurs during the thiylation of 5-trialkylsilyl-1-phenylpent-1-en-4-yn-3-ones. There are some certain regularities determined for observed reactions. We also developed stereoselective methods for the S-containing polyunsaturated compounds obtaining.

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S. A. Sokov

Togliatti State University; Ufa State Petroleum Technological University

Author for correspondence.
Email: aleksandgolovanov@yandex.ru
ORCID iD: 0000-0002-0639-0455
Russian Federation, Togliatti; Ufa

K. V. Gordon

Togliatti State University

Email: aleksandgolovanov@yandex.ru
ORCID iD: 0000-0002-4981-3577
Russian Federation, Togliatti

S. S. Zlotskii

Ufa State Petroleum Technological University

Email: aleksandgolovanov@yandex.ru
ORCID iD: 0000-0001-6365-5010
Russian Federation, Ufa

A. A. Golovanov

Togliatti State University

Email: aleksandgolovanov@yandex.ru
ORCID iD: 0000-0001-7133-3070
Russian Federation, Togliatti

References

  1. Cheng Y.-N., Jin W.-B., Wang L.-M., Sun S.-J., Xie G. Y., You X.-F., Zhao Y.-Q., Li H.L. Lett. Org. Chem. 2016, 13, 467–473. doi: 10.2174/1570178613666160812102130
  2. Rosiak A., Christoffers J. Tetrahedron Lett. 2006, 47, 5095–5097. doi: 10.1016/j.tetlet.2006.05.080
  3. Rosiak A., Müller R.M., Christoffers J. Monatsh. Chem. 2007, 138, 13–26. doi: 10.1007/s00706-006-0571-4
  4. Huang L.F., Chen C.-W., Luh T.-Y. Org. Lett. 2007, 9, 3663–3665. doi: 10.1021/ol701579f
  5. Tseng H.-R., Luh T.Y. J. Org. Chem. 1996, 61, 8685–8686. doi: 10.1021/jo961514c
  6. Huang L.-F., Lee C.-F., Tseng J.-C., Luh T.Y. Synlett. 2006, 3173–3175. doi: 10.1002/chin.200714051
  7. Chunli, X., Bartley J.K., Enache D.I., Knight D.W., Lunn M., Lok M., Hutchings G.J. Tetrahedron Lett. 2008, 49, 2454–2456. doi: 10.1016/j.tetlet.2008.02.030
  8. Mukherjee S., Kontokosta D., Pati A., Rallapalli S., Lee D. J. Org. Chem. 2009, 74, 9206–9209. doi: 10.1021/jo901950e
  9. Bali A.K., Sunnam S.K., Kumar S., Prasad K.R. Tetrahedron. 2016, 72, 8623–8636. doi: 10.1016/j.tet.2016.11.035
  10. O’Brien K.T., Smith A.B. Org. Lett. 2019, 21, 7655–7659. doi: 10.1021/acs.orglett.9b02959
  11. Bai H.-T., Lin H.C., Luh T.-Y. J. Org. Chem. 2010, 75, 4591–4595. doi: 10.1021/jo100873z
  12. Misaki T., Kawano K., Sugimura T. J. Am. Chem. Soc. 2011, 133, 5695–5697. doi: 10.1021/ja200283n
  13. Валтон Д.Р.М. Защитные группы в органической химии. Ред. Дж. МакОми, М.: Мир, 1976, 11–13. [Walton D.R.M. Protective Groups in Organic Chemistry. Ed. J.F.W. McOmie. London–N.Y.: Plenum Press, 1973, 2–5]
  14. Глотова Т.Е., Нахманович А.С., Ярош О.Г., Романенко Л.С., Комарова Т.Н. ЖОХ. 1991, 61, 2043–2096.
  15. Wu C., Lu L.-H., Peng A.-Z., Jia G.-K., Peng C., Cao Z., Tang Z., He W.-M., Xu. X. Green Chem. 2018, 20, 3683–3688. doi: 10.1039/C8GC00491A
  16. Голованов А.А., Один И.С., Злотский С.С. Усп. хим. 2019, 88, 280–318. [Golovanov A.A., Odin I.S., Zlotskii S.S. Russ. Chem. Rev. 2019, 88, 280–318.] doi: 10.1070/RCR4808
  17. Голованов А.А., Гусев Д.М., Один И.С., Злотский С.С. ХГС. 2019, 55, 333–348. [Golovanov A.A., Gusev D.M., Odin I.S., Zlotskii S.S. Chem. Heterocycl. Compd. 2019, 55, 333–348.] doi: 10.1007/s10593-019-02462-0
  18. Шустрова Т.А., Беляев Н.Н., Стадничук М.Д. ЖОХ. 1984, 54, 2781–2783.
  19. Шустрова Т.А., Беляев Н.Н., Стадничук М.Д. ЖОХ. 1985, 55, 1777–1786.
  20. Суворова И.В., Стадничук М.Д. ЖОХ. 1984, 54, 132–139.
  21. Соков С.А., Один И.С., Злотский С.С., Голова-нов А.А. ЖОрХ. 2020, 56, 1590–1597. [Sokov S.A., Odin I.S., Zlotskii S.S., Golovanov A.A. Russ. J. Org. Chem. 2020, 56, 1758–1763.] doi: 10.31857/S0514749220100146
  22. Соков С.А., Один И.С., Гусев Д.М., Кунавин Ю.А., Вологжанина А.В., Воронова Е.Д., Голованов А.А. Изв. АН Сер. хим. 2020, 69, 305–312. [Sokov S.A., Odin I.S., Gusev D.M., Kunavin Yu.A., Vologzhanina A.V., Voronova E.D., Golovanov A.A. Russ. Chem. Bull. 2020, 69, 305–312.] doi 10.007/211172-020-2761-3
  23. Смит В.А., Бочков А.Ф., Кейпл Р. Органический синтез. Наука и искусство. М.: Мир, 2001, 181–195.
  24. Kaumanns O., Mayr H. J. Org. Chem. 2008, 73, 2738–2745. doi: 10.1021/jo702590s
  25. Kaumanns O., Lucius R., Mayr H. Chem. Eur. J. 2008, 14, 9675–9682. doi: 10.1002/chem.200801277
  26. Голованов А.А., Гусев Д.М., Вологжанина А.В., Бекин В.В., Писарева В.С. ЖОрХ. 2014, 50, 21–28. [Golovanov A.A., Gusev D.M., Vologzhanina A.V., Bekin V.V., Pisareva V.S. Russ. J. Org. Chem. 2014, 50, 13–20.] doi: 10.1134/S1070428014010035
  27. Hwu R.J.-R., Tsay S.-C., Cheng B.-L. The Chemistry of Organic Silicon Compounds. Vol. 2. Ed. Z. Pappoport, Y. Apeloig. Chichester–N.Y.–Weinheim–Brisbane–Singapore–Toronto: John Wiley & Sons, 1998, 433.
  28. Стацюк В.Е., Краснов В.Л., Коршунов С.П., Бодриков И.В. ЖОрХ. 1983, 19, 468–475.
  29. Golubev P., Karpova E.A., Pankova E.A., Sorokina M., Kuznetsov M.A. J. Org. Chem. 2016, 81, 11268–11275. doi: 10.1021/acs.joc.6b02217
  30. Климова В.А. Основные микрометоды анализа органических соединений. М.: Химия, 1975, 51–56.
  31. Гельман Н.Э., Терентьева Н.А., Шанина Г.М., Кипаренко Л.М., Резл В. Методы количественного органического микроанализа. М.: Химия, 1987, 233–234.
  32. Brandsma L. Synthesis of Acetylenes Allenes and Cumulenes. Methods and Techniques. Amsterdam: Elsevier, 2004, 144.
  33. Holmes A.B., Sporikou C.N. Org. Synth. 1987, 65, 61. doi: 10.15227/orgsyn.065.0061
  34. West R., Quass L.C. J. Organometal. Chem. 1969, 18, 55–67. doi: 10.1016/S0022-328X(00)80233-8
  35. Müller M., Forster W.-R., Holst A., Kingma A. J., Schaumann E., Adiwidjaja G. Chem Eur. J. 1996, 2, 949–956. doi: 10.1002/chem.19960020809
  36. Belil C., Pascual J., Serratosa F. Tetrahedron. 1964, 20, 2701–2708. doi: 10.1016/S0040-4020(01)90851-8
  37. Attenburrow J., Cameron A.F.B., Campton J.H., Evans R.M., Hems B. A., Jansen A.B.A., Walker T. J. Chem. Soc. 1952, 1094–1111. doi: 10.1039/JR9520001094

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