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Synlett 2022; 33(04): 386-390
DOI: 10.1055/s-0041-1737760
letter

Synthesis of 2-Arylbenzothiazoles from Nitrobenzenes, Benzylamines, and Elemental Sulfur via Redox Cyclization

Masahiro Teramoto∗
a   Seika Corporation, 1660-627, Nishihama, Wakayama 641-0036, Japan
b   Department of Applied Chemistry, Graduate School of Engineering, Osaka Prefecture University, 1-1 Gakuen-cho, Naka-ku, Sakai, Osaka 599-8531, Japan
,
Mitsutaka Imoto
a   Seika Corporation, 1660-627, Nishihama, Wakayama 641-0036, Japan
,
Motonori Takeda
a   Seika Corporation, 1660-627, Nishihama, Wakayama 641-0036, Japan
,
Takumi Mizuno  ∗
a   Seika Corporation, 1660-627, Nishihama, Wakayama 641-0036, Japan
,
Akihiro Nomoto
b   Department of Applied Chemistry, Graduate School of Engineering, Osaka Prefecture University, 1-1 Gakuen-cho, Naka-ku, Sakai, Osaka 599-8531, Japan
,
Akiya Ogawa
b   Department of Applied Chemistry, Graduate School of Engineering, Osaka Prefecture University, 1-1 Gakuen-cho, Naka-ku, Sakai, Osaka 599-8531, Japan
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Abstract

A sustainable advanced synthetic method was developed based on redox cyclization for the synthesis of 2-arylbenzothiazoles in good to excellent yields from readily available nitrobenzenes, benzylamines, and elemental sulfur without the use of transition-metal catalysts. This method is remarkable: nitro group reduction, a benzylamine redox reaction, sulfuration, condensation, and cyclization, all proceed in a single step to generate a heterocycle. It is also highly atom-economical and does not require any external oxidizing or reducing agents.

Key words

redox cyclization - benzothiazoles - nitrobenzenes - benzylamines - elemental sulfur - atom-economical

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0041-1737760.
  • Supporting Information


Publication History

Received: 16 November 2021

Accepted after revision: 14 December 2021

Article published online:
18 January 2022

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  • References and Notes

    • 1a Ram VJ, Sethi A, Nath M, Pratap R. The Chemistry of Heterocycles . Elsevier; Amsterdam: 2017. Chap. 5, 149
      Google Scholar
    • 1b Mondal J, Sreejith S, Borah P, Zhao Y. ACS Sustainable Chem. Eng. 2014; 2: 934
      Crossref
    • 1c Behrsing HP, Furniss MJ, Davis M, Tomaszewski JE, Parchment RE. Toxicol. Sci. 2013; 131: 470
      CrossrefPubMed
  • 2 Biancalana M, Koide S. Biochim. Biophys. Acta 2010; 1804: 1405
    CrossrefPubMed
  • 3 Sakai J, Miura I, Shibata M, Yonekura N, Hiyoshi H, Takagaki M, Nagayama K. J. Pestic. Sci. 2010; 35: 488
    Crossref
    • 4a Wang S, Bao G, Lu Z, Wu P, Han Z. J. Mater. Sci. 2000; 35: 5873
      Crossref
    • 4b Fratini AV, Cross EM, O’Brien JF, Adams WW. J. Macromol. Sci. B 1985; 24: 159
      Crossref
    • 4c Yabuki K, Kato K. Sen’i Gakkaishi 1996; 52: 143
      Crossref
  • 5 Nguyen TB, Ermolenko L, Retailleau P, Al-Mourabit A. Angew. Chem. Int. Ed. 2014; 53: 13808
    CrossrefPubMed
  • 6 Xing Q, Ma Y, Xie H, Xiao F, Zhang F, Deng GJ. J. Org. Chem. 2019; 84: 1238
    CrossrefPubMed
  • 7 Pham HT, Ho TH, Do DQ, Nguyen KL. H, Nguyen TT, Phan NT. S. Synlett 2020; 31: 1813
    Article in Thieme Connect
  • 8 Teramoto M, Imoto M, Takeda M, Mizuno T, Nomoto A, Ogawa A. J. Org. Chem. 2020; 85: 15213
    CrossrefPubMed

      • For related sulfur-promoted heterocycle synthesis, see:
    • 9a Liu S, Deng G.-J, Huang H. Synlett 2021; 32: 142
      Article in Thieme Connect
    • 9b Nguyen TB. Adv. Synth. Catal. 2020; 362: 3448
      CrossrefPubMed
    • 9c Nguyen TB. Adv. Synth. Catal. 2017; 359: 1066
      Crossref
    • 9d Nguyen TB. Asian J. Org. Chem. 2017; 6: 477
      Crossref
    • 9e Nguyen LA, Ngo QA, Retailleau P, Nguyen TB. Green Chem. 2017; 19: 4289
      Crossref
    • 9f Nguyen TB, Ermolenko L, Al-Mourabit A. Org. Lett. 2013; 15: 4218
      CrossrefPubMed
  • 10 Gao MY, Li JH, Zhang SB, Chen LJ, Li YS, Dong ZB. J. Org. Chem. 2020; 85: 493
    CrossrefPubMed
  • 11 Singla AK, Chawla M, Singh A. J. Pharm. Pharmacol. 2000; 52: 467
    CrossrefPubMed
  • 12 Bennett A, Villa G. Expert Opin. Pharmacother. 2000; 1: 277
    CrossrefPubMed
  • 13 Nguyen TB, Ermolenko L, Dean WA, Al-Mourabit A. Org. Lett. 2012; 14: 5948
    CrossrefPubMed