New strategy for the synthesis of 3-ethynyl-2-(thiophen-2-yl)benzo[b]thiophene derivatives
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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.
KeywordsAlkynes Benzothiophenes Sonogashira coupling reaction C–C bond formation reactions
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.
- 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
- 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
- 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