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Convenient Synthesis of Benzo[b]thiophene-5,6-dicarboximide Derivatives and Their Photophysical Properties

Received: 05 October 2016    Accepted: 18 October 2016    Published: 10 November 2016
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Abstract

Phosphine-assisted annulation of thiophene-2,3-dicarbaldehyde with N-substituted maleimides provided the N-substituted benzo[b]thiophene-5,6-dicarboximides in good to high yields. Introduction of cyano and aryl groups to the thiophene moiety of the N-cyclohexyl product was achieved by metal-catalyzed coupling reactions via its bromo derivative. Photophysical properties of the products were also reported.

DOI 10.11648/j.mc.20160405.11
Published in Modern Chemistry (Volume 4, Issue 5, October 2016)
Page(s) 45-51
Creative Commons

This is an Open Access article, distributed under the terms of the Creative Commons Attribution 4.0 International License (http://creativecommons.org/licenses/by/4.0/), which permits unrestricted use, distribution and reproduction in any medium or format, provided the original work is properly cited.

Copyright

Copyright © The Author(s), 2024. Published by Science Publishing Group

Keywords

Annulation, Phosphine, Copper-Mediated Cyanation, Mizoroki-Heck Reaction, Emission

References
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[10] H. Shimosasa, R. Miyatake, N. Kobayashi, and M. Oda “Synthesis and emission behavior of 1,3-diarylisobenzofuran- 5,6-dicarboximides and their transformation into naphthalene-2,3:6,7-bis(diacboximide)s”, Modern Chem. 2016, 4 (6), 16–23.
[11] T. Yanagisawa, N. Kobayashi, H. Shimosasa, Y. Kumai, R. Miyatake, and M. Oda, “Synthesis and fluorescence property of 2,3-naphthalimie deriveatives bearing phenyl substituents on the naphthalene skeleton”, Dyes Pigments in press, http://dx.doi.org/10.1016/j.dyepig.2016.09.050.
[12] M. J. Haddadin, B. J. Agha, and R. F. Tabri, “Syntheses of some furans and naphtho[2,3-c] derivatives of furan, pyrrole, and thiophene”, J. Org. Chem. 1979, 44, 494–497.
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[15] For examples, an emission quantum yield of N-ethylnaphthlene-2,3-dicarboximide, corresponding to 6b, in chloroform is 0.37 and that of N-phenylnaphthalene- 2,3-dicarboximide, corresponding to 6d, is 0.10.
[16] The low quantum yields of 6e and 6f are ascribed also to a heavy atom effect of the bromine and iodine atoms.
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[18] Although Lemaire et al. reported cyanation of 3-bromobenzo[b]thiophene with CuCN in N,N-dimthylacetamide in ref 9, cyanation of 12 under the similar conditions yielded 13 in low yield.
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[22] Although the 13C NMR spectrum of 20b in CDCl3 shows only 19 signals, which are short for the structure of 20b, the spectrum in CD2Cl2 indicates 20 signals enough for the structure of 20b.
Author Information
  • Department of Chemistry, Faculty of Science, Shinshu University, Nagano, Japan

  • Department of Chemistry, Faculty of Science, Shinshu University, Nagano, Japan

  • Department of Chemistry, Faculty of Science, Shinshu University, Nagano, Japan

  • Department of Chemistry, Faculty of Science, Shinshu University, Nagano, Japan

  • Centre for Environmental Conservation and Research Safety, University of Toyama, Toyama, Japan

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  • APA Style

    Naoki Kobayashi, Shinya Yamamoto, Haruki Shimosasa, Mitsunori Oda, Ryuta Miyatake. (2016). Convenient Synthesis of Benzo[b]thiophene-5,6-dicarboximide Derivatives and Their Photophysical Properties. Modern Chemistry, 4(5), 45-51. https://doi.org/10.11648/j.mc.20160405.11

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    ACS Style

    Naoki Kobayashi; Shinya Yamamoto; Haruki Shimosasa; Mitsunori Oda; Ryuta Miyatake. Convenient Synthesis of Benzo[b]thiophene-5,6-dicarboximide Derivatives and Their Photophysical Properties. Mod. Chem. 2016, 4(5), 45-51. doi: 10.11648/j.mc.20160405.11

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    AMA Style

    Naoki Kobayashi, Shinya Yamamoto, Haruki Shimosasa, Mitsunori Oda, Ryuta Miyatake. Convenient Synthesis of Benzo[b]thiophene-5,6-dicarboximide Derivatives and Their Photophysical Properties. Mod Chem. 2016;4(5):45-51. doi: 10.11648/j.mc.20160405.11

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  • @article{10.11648/j.mc.20160405.11,
      author = {Naoki Kobayashi and Shinya Yamamoto and Haruki Shimosasa and Mitsunori Oda and Ryuta Miyatake},
      title = {Convenient Synthesis of Benzo[b]thiophene-5,6-dicarboximide Derivatives and Their Photophysical Properties},
      journal = {Modern Chemistry},
      volume = {4},
      number = {5},
      pages = {45-51},
      doi = {10.11648/j.mc.20160405.11},
      url = {https://doi.org/10.11648/j.mc.20160405.11},
      eprint = {https://download.sciencepg.com/pdf/10.11648.j.mc.20160405.11},
      abstract = {Phosphine-assisted annulation of thiophene-2,3-dicarbaldehyde with N-substituted maleimides provided the N-substituted benzo[b]thiophene-5,6-dicarboximides in good to high yields. Introduction of cyano and aryl groups to the thiophene moiety of the N-cyclohexyl product was achieved by metal-catalyzed coupling reactions via its bromo derivative. Photophysical properties of the products were also reported.},
     year = {2016}
    }
    

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    T1  - Convenient Synthesis of Benzo[b]thiophene-5,6-dicarboximide Derivatives and Their Photophysical Properties
    AU  - Naoki Kobayashi
    AU  - Shinya Yamamoto
    AU  - Haruki Shimosasa
    AU  - Mitsunori Oda
    AU  - Ryuta Miyatake
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    JO  - Modern Chemistry
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    AB  - Phosphine-assisted annulation of thiophene-2,3-dicarbaldehyde with N-substituted maleimides provided the N-substituted benzo[b]thiophene-5,6-dicarboximides in good to high yields. Introduction of cyano and aryl groups to the thiophene moiety of the N-cyclohexyl product was achieved by metal-catalyzed coupling reactions via its bromo derivative. Photophysical properties of the products were also reported.
    VL  - 4
    IS  - 5
    ER  - 

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