DOI QR코드

DOI QR Code

The Synthesis of Novel Mono(alkoxy)-, Tris(thio)- and Tetrakis(thio)-Substituted Quinones from the Reactions of p-Chloranil with Various S-Nucleophiles

  • Ibis, Cemil (Istanbul University, Faculty of Engineering, Department of Chemistry) ;
  • Yildiz, Mahmut (Istanbul University, Hasan Ali Yucel Faculty of Education) ;
  • Sayil, Cigdem (Istanbul University, Faculty of Engineering, Department of Chemistry)
  • 발행 : 2009.10.20

초록

The tetrakis(thio)-substituted-1,4-benzoquinone products 4a-e, 6, 7, and the mono(alkoxy)-tris(thio)-substituted-1,4- benzoquinone products 5a-e and 8a-e were synthesized from the reactions of p-chloranil with some thiols and mixture of two different thiol compounds in alcohol in the presence of $Na_2CO_3$ at room temperature. The structures of the novel S,S,S,S- and S,S,S,O- substituted products, which were obtained by the reactions of p-chloranil as a starting compound with n-propanethiol, n-pentanethiol, n-decanethiol, n-dodecanethiol, 2-methyl-2-propanethiol, and mixture of n-decanethiol and n-cyclohexanethiol as S-nucleophiles, were characterized by spectroscopic methods.

키워드

참고문헌

  1. McReynolds, M. D.; Doughtery, J. M.; Hanson, P. R. Chem. Rev. 2004, 104, 2239. https://doi.org/10.1021/cr020109k
  2. Zhu, J. Synletters 1997, 2, 133.
  3. Becker, J. Y.; Bernstein, J.; Bittner, S.; Harlev, E.; Sarma, J. A. R. P.; Saik, S. S. New J. Chem. 1988, 12, 875.
  4. Otsubo, T.; Nobuhara, Y.; Kanefuji, K.; Aso, Y.; Ogura, F. J. Phys. Org. Chem. 1988, 1, 275. https://doi.org/10.1002/poc.610010505
  5. Vanelle, P.; Terme, T.; Crozet, M. P. Tetrahedron Lett. 2000, 41, 6383. https://doi.org/10.1016/S0040-4039(00)01069-8
  6. Mohanda, J.; Chennell, A. F.; Duggin, G. G.; Horvat, J. S.; Til Horvat ler, D. J. Carcinogenesis 1986, 7, 353. https://doi.org/10.1093/carcin/7.3.353
  7. Bittner, S.; Lemperit, D. Synthesis 1994, 9, 917
  8. Smith, M. T. J. Toxical. Environ. Health 1985, 16, 665. https://doi.org/10.1080/15287398509530776
  9. Batra, M.; Kriplani, P.; Batra, C.; Ojha, K. G. Bioorganic & Medicinal Chemistry 2006, 14, 8519 https://doi.org/10.1016/j.bmc.2006.08.036
  10. Tjepkema, J. J. Rec. Trav. Chim. 1952, 71, 853.
  11. Takagi, K.; Mizuno, A.; Iwamoto, A.; Furusyo, M.; Matsuoka, M. Dyes and Pigments 1998, 36(1), 35. https://doi.org/10.1016/S0143-7208(97)80865-0
  12. Goksel, F. S.; Ibis, C.; Bayrak, N. A. Phosphorus, Sulfur, and Silicon 2005, 180, 1961. https://doi.org/10.1080/104265090902723
  13. Ibis, C.; Gunes Z. O. Dyes and Pigments 2008, 77(1), 39. https://doi.org/10.1016/j.dyepig.2007.02.010
  14. Romanyuk, A. L.; Litvin, B. L.; Ganushchak, N. I.; Vishnevskii, R. M. Russain Journal of General Chemistry 2006, 76(11), 1834 https://doi.org/10.1134/S1070363206110284
  15. Murata, T.; Morita, Y.; Fukui, K.; Sato, K.; Shiomi, D.; Takui, T.; Maesato, M.; Yamochi, H.; Saito, G.; Nakasuji, K. Angew. Chem. Int. Ed. 2004, 43, 6343. https://doi.org/10.1002/anie.200460801
  16. Aslan, M.; Masnovi, J. Spectrochimica Acta Part A 2006, 64, 711. https://doi.org/10.1016/j.saa.2005.07.073
  17. Horiuchi, S.; Kumai, R.; Okimoto, Y.; Tokura, Y. Synthetic Metals 2003, 133-134, 615 https://doi.org/10.1016/S0379-6779(02)00367-3
  18. Takeya, T.; Kondo, H.; Otsuka, T.; Doi, H.; Okamoto, I.; Kotani, E. Chem. Pharm. Bull. 2005, 53(2), 199. https://doi.org/10.1248/cpb.53.199
  19. Gaber, M.; Al-Shihry, S. S. Spectrochimica Acta Part A 2005, 62, 526. https://doi.org/10.1016/j.saa.2005.02.005
  20. Sadeghi, S.; Karimi, E. Chem. Pharm. Bull. 2006, 54(8), 1107 https://doi.org/10.1248/cpb.54.1107
  21. Marder, S. R. Metal Containing Materials for Nonlinear Optics, Inorganic Materials. 2nd ed.; Bruce D. W; Hare D. O'., Eds.; Chichester: Wiley, 1996; p 121.
  22. Tjepkema, J. J. Manufacture of Organomercapto-substituted Quinones, U. S. 2,691,661; October 12, 1954.
  23. Matsumoto, S.; Miura, H.; Mizuguchi, J. Dyes Pigments 2002, 52, 9. https://doi.org/10.1016/S0143-7208(01)00082-1
  24. Matsumoto, S.; Mizuguchi, J. Acta Crystallographica Section B 2001, 57, 82. https://doi.org/10.1107/S0108768100014087
  25. Sammis, J. L. J. Am. Chem. Soc. 1905, 27, 1120. https://doi.org/10.1021/ja01987a009
  26. Yoshioka, T.; Kurumada, T.; Yamazaki, M. 2-Mercaptoquinone Derivate, J. P. 57085366; May 28, 1982.
  27. Raymond, C. S. Tetra-T-Dodecylamarcapto-p-Benzoquinone, U. S. 3764535; October 9, 1973
  28. Snell, J. M.; Weissberger, A. J. Am. Chem. Soc. 1938, 61, 450. https://doi.org/10.1021/ja01871a065
  29. Bittner, S.; Meenakshi, C.; Temtsin, G. Tetrahedron 2001, 57, 7423. https://doi.org/10.1016/S0040-4020(01)00717-7

피인용 문헌

  1. The Synthesis, Spectral, and Electrochemical Characterization of Novel Alkoxybenzoquinone Derivatives vol.53, pp.3, 2016, https://doi.org/10.1002/jhet.1668
  2. ChemInform Abstract: The Synthesis of Novel Mono(alkoxy)-, Tris(thio)- and Tetrakis(thio)-Substituted Quinones from the Reactions of p-Chloranil with Various S-Nucleophiles. vol.41, pp.13, 2010, https://doi.org/10.1002/chin.201013083
  3. Synthesis, Antimicrobial Properties, and Inhibition of Catalase Activity of 1,4-Naphtho- and Benzoquinone Derivatives Containing N-, S-, O-Substituted vol.2019, pp.1098-1071, 2019, https://doi.org/10.1155/2019/1658417
  4. The synthesis of new cyclic thioquinone derivatives vol.21, pp.6, 2009, https://doi.org/10.1002/hc.20634
  5. Synthesis and Characterization of Novel N-, S-, O-Substituted P-Chloranil Derivatives vol.44, pp.11, 2014, https://doi.org/10.1080/00397911.2013.865059
  6. Synthesis of Novel S,O-Substituted 1,4-Benzoquinones vol.189, pp.1, 2009, https://doi.org/10.1080/10426507.2013.798787
  7. The Synthesis, Characterization, and Electrochemical Investigation of Novel Thio- and Alkoxy-Substituted Benzoquinone Derivatives vol.189, pp.4, 2014, https://doi.org/10.1080/10426507.2013.829833
  8. Synthesis and antiproliferative evaluation of some 1,4-naphthoquinone derivatives against human cervical cancer cells vol.17, pp.1, 2009, https://doi.org/10.1515/chem-2019-0030
  9. Synthesis and antiproliferative evaluation of some 1,4-naphthoquinone derivatives against human cervical cancer cells vol.17, pp.1, 2009, https://doi.org/10.1515/chem-2019-0030
  10. Synthesis, electrochemistry, in-situ spectroelectrochemistry and molecular structures of 1,4-naphthoquinone derivatives vol.1224, pp.None, 2021, https://doi.org/10.1016/j.molstruc.2020.129145