Advertisement

Chemical Papers

, Volume 73, Issue 4, pp 977–985 | Cite as

New strategy for the synthesis of 3-ethynyl-2-(thiophen-2-yl)benzo[b]thiophene derivatives

  • Muheb A. S. Algso
  • Arif KivrakEmail author
Original Paper
  • 102 Downloads

Abstract

Pd-catalyzed coupling reactions like the Sonogashira coupling reaction are very useful tools for the formation of new carbon–carbon bonds under mild reaction conditions. Coupling reactions are also used for elaboration of organic compounds in drug and material discovery. Terminal alkynes have a very critical role in Sonogashira coupling reaction. Therefore, design and synthesis of new terminal alkynes are very important for the preparation of organic compounds. In the present study, a novel alkyne 3-ethynyl-2-(thiophen-2-yl)benzo[b]thiophene 13 was synthesized, and it was tested for Sonogashira coupling reaction with different iodoaryl compounds. It was investigated whether our terminal alkyne 13 having a special construction might be a useful precursor for the synthesis of potentially active organic molecules.

Keywords

Alkynes Benzothiophenes Sonogashira coupling reaction C–C bond formation reactions 

Notes

Acknowledgements

The authors thank The Scientific and Technological Research Council of Turkey (Project no: 115Z020) for providing financial support for obtaining reactant and reagents, and Van Yüzüncü Yil University (Project no: FBA-2017-6007) for providing financial support for obtaining solvents, glasswares and salts. We thank University of Duhok for the scholarship given to Muheb A.S. Algso. The authors would also like to acknowledge networking contribution by the COST Action CM1407.

Supplementary material

11696_2018_640_MOESM1_ESM.doc (41 mb)
Characterization of the new benzo[b]thiophene products including 1H NMR, 13C NMR, and FTIR spectra, as well as mass characterization data. (DOC 42003 kb)

References

  1. Algso MAS, Kivrak A, Konus M, Yilmaz C, Kurt-Kizildogan A (2018) Synthesis and biological evaluation of novel benzothiophene derivatives. J Chem Sci.  https://doi.org/10.1007/s12039-018-1523-3 Google Scholar
  2. Brasholz M, Reissig HU, Zimmer R (2009) Sugars, alkaloids, and heteroaromatics: exploring heterocyclic chemistry with alkoxyallenes. Acc Chem Res 42(1):45–56.  https://doi.org/10.1021/ar800011h CrossRefGoogle Scholar
  3. Chen CC, Chen CM, Wu MJ (2014) Transition metal-catalyzed cascade cyclization of aryldiynes to halogenated benzo b naphtho 2,1-d thiophene derivatives. J Org Chem 79(10):4704–4711.  https://doi.org/10.1021/jo500377v CrossRefGoogle Scholar
  4. Coa JC, Castrillon W, Cardona W, Carda M, Ospina V, Munoz JA, Velez ID, Robledo SM (2015) Synthesis, leishmanicidal, trypanocidal and cytotoxic activity of quinoline-hydrazone hybrids. Eur J Med Chem 101:746–753.  https://doi.org/10.1016/j.ejmech.2015.07.018 CrossRefGoogle Scholar
  5. Croxtall JD, Plosker GL (2009) Sertaconazole A review of ıts use in the management of superficial mycoses in dermatology and gynaecology. Drugs 69(3):339–359CrossRefGoogle Scholar
  6. Guo SH, He YW, Murtaza I, Tan JH, Pan JY, Guo YT, Zhu YN, He Y, Meng H (2018) Alkoxy substituted 1 benzothieno 3,2-b 1 benzothiophene derivative with improved performance in organic thin film transistors. Org Electron 56:68–75.  https://doi.org/10.1016/j.orgel.2018.02.003 CrossRefGoogle Scholar
  7. Katritzky AR, Karelson M, Sild S, Krygowski TM, Jug K (1998) Aromaticity as a quantitative concept. 7. Aromaticity reaffirmed as a multidimensional characteristic. J Org Chem 63(15):5228–5231.  https://doi.org/10.1021/jo970939b CrossRefGoogle Scholar
  8. Kazemizadeh AR, Shajari N, Shapouri R, Adibpour N, Teimuri-Mofrad R (2016) Synthesis and anti-brucella activity of some new 1,3,4-oxadiazole derivatives containing a ferrocene unit. J Iran Chem Soc 13(7):1349–1355.  https://doi.org/10.1007/s13738-016-0849-3 CrossRefGoogle Scholar
  9. Kivrak A, Larock RC (2010) Synthesis of dihydrobenzisoxazoles by the 3 + 2 cycloaddition of arynes and oxaziridines. J Org Chem 75(21):7381–7387.  https://doi.org/10.1021/jo101656c CrossRefGoogle Scholar
  10. Kumar S, Mujahid M, Verma AK (2017) Regioselective 6-endo-dig iodocyclization: an accessible approach for iodo-benzo a phenazines. Org Biomol Chem 15(21):4686–4696.  https://doi.org/10.1039/c7ob00671c CrossRefGoogle Scholar
  11. Lu WD, Wu MJ (2007) Halocyclization of 2-alkynylthioanisoles by cupric halides: synthesis of 2-substituted 3-halobenzo b thiophenes. Tetrahedron 63(2):356–362.  https://doi.org/10.1016/j.tet.2006.10.068 CrossRefGoogle Scholar
  12. Meixner CN, Aref MW, Gupta A, McNerny EMB, Brown D, Wallace JM, Allen MR (2017) Raloxifene improves bone mechanical properties in mice previously treated with zoledronate. Calcif Tissue Int 101(1):75–81.  https://doi.org/10.1007/s00223-017-0257-4 CrossRefGoogle Scholar
  13. Miao MZ, Xu HP, Luo Y, Jin MC, Chen ZK, Xu JF, Ren HJ (2017) A modular approach to highly functionalized 3-sulfonylfurans via conjugate addition of 3-cyclopropylideneprop-2-en-1-ones with sodium sulfinates and sequential 5-endo-trig iodocyclization. Org Chem Front 4(9):1824–1828.  https://doi.org/10.1039/c7qo00362e CrossRefGoogle Scholar
  14. Pathak RB, Chovatia PT, Parekh HH (2012) Synthesis, antitubercular and antimicrobial evaluation of 3-(4-chlorophenyl)-4-substituted pyrazole derivatives. Bioorg Med Chem Lett 22(15):5129–5133.  https://doi.org/10.1016/j.bmcl.2012.05.063 CrossRefGoogle Scholar
  15. Rafiq SM, Sivasakthikumaran R, Mohanakrishnan AK (2014) Lewis acid/Bronsted acid mediated benz-annulation of thiophenes and electron-rich arenes. Org Lett 16(10):2720–2723.  https://doi.org/10.1021/ol501006t CrossRefGoogle Scholar
  16. Rahmouni A, Souiei S, Belkacem MA, Romdhane A, Bouajila J, Ben Jannet H (2016) Synthesis and biological evaluation of novel pyrazolopyrimidines derivatives as anticancer and anti-5-lipoxygenase agents. Bioorg Chem 66:160–168.  https://doi.org/10.1016/j.bioorg.2016.05.001 CrossRefGoogle Scholar
  17. Richardson DR, Kalinowski DS, Lau S, Jansson PJ, Lovejoy DB (2009) Cancer cell iron metabolism and the development of potent iron chelators as anti-tumour agents. Biochim Biophys Acta Gen Subj 1790(7):702–717.  https://doi.org/10.1016/j.bbagen.2008.04.003 CrossRefGoogle Scholar
  18. Sarret C, Pichard S, Afenjar A, Boespflug-Tanguy O (2017) Lack of long-term neurologic efficacy of zileuton in Sjogren–Larsson’s syndrome. Neuropediatrics 48(3):205–206.  https://doi.org/10.1055/s-0037-1601856 CrossRefGoogle Scholar
  19. Shakdofa MME, Shtaiwi MH, Morsy N, Abdel-rassel TMA (2014) Metal complexes of hydrazones and their biological, analytical and catalytic applications: a review. Main Group Chem 13(3):187–218.  https://doi.org/10.3233/mgc-140133 Google Scholar
  20. Sun LL, Deng CL, Tang RY, Zhang XG (2011) CuI/TMEDA-catalyzed annulation of 2-bromo alkylbenzenes with Na2S: synthesis of benzo b thiophenes. J Org Chem 76(18):7546–7550.  https://doi.org/10.1021/jo201081v CrossRefGoogle Scholar
  21. Togo H, Iida S (2006) Synthetic use of molecular iodine for organic synthesis. Synlett 14:2159–2175.  https://doi.org/10.1055/s-2006-950405 CrossRefGoogle Scholar
  22. Vogel VG, Costantino JP, Wickerham DL, Cronin WM, Cecchini RS, Atkins JN, Bevers TB, Fehrenbacher L, Pajon ER, Wade JL, Robidoux A, Margolese RG, James J, Lippman SM, Runowicz CD, Ganz PA, Reis SE, McCaskill-Stevens W, Ford LG, Jordan VC, Wolmark N, Nsabp (2006) Effects of tamoxifen vs raloxifene on the risk of developing invasive breast cancer and other disease outcomes—the NSABP study of tamoxifen and raloxifene (STAR) P-2 trial. JAMA J Am Med Assoc 295(23):2727–2741.  https://doi.org/10.1001/jama.295.23.joc60074 CrossRefGoogle Scholar
  23. Weiser M, Levi L, Burshtein S, Hagin M, Matei VP, Podea D, Miclutia I, Tiugan A, Pacala B, Grecu IG, Noy A, Zamora D, Davis JM (2017) Raloxifene plus antipsychotics versus placebo plus antipsychotics in severely Ill decompensated postmenopausal women with schizophrenia or schizoaffective disorder: a randomized controlled trial. J Clin Psychiatry 78(7):E758.  https://doi.org/10.4088/jcp.15m10498 CrossRefGoogle Scholar
  24. Yaragorla S, Pareek A, Dada R, Saini PL (2017) Single-step synthesis of 3-iodoquinolines from 2-aminophenyl ketones through a regioselective (6-endo-dig) electrophilic cyclization. Eur J Org Chem 31:4600–4608.  https://doi.org/10.1002/ejoc.201700668 CrossRefGoogle Scholar
  25. Yue DW, Larock RC (2004) Synthesis of 3-iodoindoles by electrophilic cyclization of N, N-dialkyl-2-(1-alkynyl)anilines. Org Lett 6(6):1037–1040.  https://doi.org/10.1021/ol0498996 CrossRefGoogle Scholar
  26. Zora M, Kivrak A, Yazici C (2011) Synthesis of pyrazoles via electrophilic cyclization. J Org Chem 76(16):6726–6742.  https://doi.org/10.1021/jo201119e CrossRefGoogle Scholar

Copyright information

© Institute of Chemistry, Slovak Academy of Sciences 2018

Authors and Affiliations

  1. 1.Department of ChemistryVan Yüzüncü Yil UniversityVanTurkey

Personalised recommendations