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Synthesis 2021; 53(05): 971-977
DOI: 10.1055/s-0040-1706104
paper

Insertion Reaction of 2-Halo-N-allylanilines with K2S Involving Trisulfur Radical Anion: Synthesis of Benzothiazole Derivatives under Transition-Metal-Free Conditions

Xin-Yu Liu
a   Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science & Collaborative Innovation Center of Suzhou Nano Science and Technology, Soochow University, Suzhou 215123, P. R. of China
,
Yan-Wei Zhao∗
a   Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science & Collaborative Innovation Center of Suzhou Nano Science and Technology, Soochow University, Suzhou 215123, P. R. of China
,
Tian Jiang
a   Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science & Collaborative Innovation Center of Suzhou Nano Science and Technology, Soochow University, Suzhou 215123, P. R. of China
,
Weidong Rao
b   Nanjing Forest University, Nanjing 210037, P. R. of China
,
Shun-Yi Wang  ∗
a   Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science & Collaborative Innovation Center of Suzhou Nano Science and Technology, Soochow University, Suzhou 215123, P. R. of China
› InstitutsangabenWe gratefully acknowledge the National Natural Science Foundation of China (21971174 and 21772137), PAPD, the Major Basic Research Project of the Natural Science Foundation of the Jiangsu Higher Education Institutions (No. 16KJA150002), the Project of Scientific and Technologic Infrastructure of Suzhou (SZS201708), Soochow University, and State and Local Joint Engineering Laboratory for Novel Functional Polymeric Materials for financial support.
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Abstract

A synthesis of benzothiazole derivatives through the reaction of 2-halo-N-allylanilines with K2S in DMF is developed. The trisulfur radical anion S3·–, which is generated in situ from K2S in DMF, initiates the reaction without transition-metal catalysis or other additives. In addition, two C–S bonds are formed and heteroaromatization of benzothiazole is triggered by radical cyclization and H-shift.

Keywords

transition metal-free - trisulfur radical anion - benzothiazole derivatives - radicals - cyclization

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1706104.
  • Supporting Information


Publikationsverlauf

Eingereicht: 04. November 2020

Angenommen nach Revision: 19. November 2020

Artikel online veröffentlicht:
14. Dezember 2020

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  • References

    • 1a Ueki M, Ueno K, Miyadoh S, Abe K, Shibata K, Taniguchi M, Oi S. J. Antibiot. 1993; 46: 1089
      CrossrefPubMed
    • 1b Don M.-J, Shen C.-C, Lin Y.-L, Syu W, Ding Y.-H, Sun C.-M. J. Nat. Prod. 2005; 68: 1066
      CrossrefPubMed
    • 1c Sato S, Kajiura T, Noguchi M, Takehana K, Kobayashi T, Tsuji T. J. Antibiot. 2001; 54: 102
      CrossrefPubMed
    • 1d Davidson J, Corey PE. J. J. Am. Chem. Soc. 2003; 125: 13486
      CrossrefPubMed
    • 1e Wang N.-Z, Saidhareddy P.-l, Jiang X.-F. Nat. Prod. Rep. 2020; 37: 246
      CrossrefPubMed
    • 2a Jiang L.-L, Tan Y, Zhu X.-L, Wang Z.-F, Zuo Y, Chen Q, Xi Z, Yang G.-F. J. Agric. Food Chem. 2010; 58: 2643
      CrossrefPubMed
    • 2b Naya A, Kobayashi K, Ishikawa M, Ohwaki K, Saeki T, Noguchi K, Ohtake N. Bioorg. Med. Chem. Lett. 2001; 11: 1219
      CrossrefPubMed
    • 2c Candeias NR, Branco LC, Gois PM. P, Afonso CA. M, Trindade AF. Chem. Rev. 2009; 109: 2703
      CrossrefPubMed
    • 2d Wu X.-F, Neumann H, Beller M. Chem. Rev. 2013; 113: 1
      CrossrefPubMed
    • 2e Yuan J, Liu C, Lei A.-W. Chem. Commun. 2015; 51: 1394
      CrossrefPubMed
    • 2f Feng M.-H, Tang B.-Q, Liang S.-H, Jiang X.-f. Curr. Top. Med. Chem. 2016; 16: 1200
      CrossrefPubMed
    • 3a Cao D.-W, Yan C.-X, Zhou P.-P, Zeng H.-Y, Li C.-J. Chem. Commun. 2019; 55: 767
      CrossrefPubMed
    • 3b Discekici EH, Treat NJ, Poelma SO, Mattson KM, Hudson ZM, Luo Y.-D, Hawker CJ, Alaniz J. Chem. Commun. 2015; 51: 11705
      CrossrefPubMed
    • 4a Röder L, Nicholls AJ, Baxendale IR. Molecules 2019; 24: 1996
      CrossrefPubMed
    • 4b Fang L, Qi L, Ye L.-F, Pan Z.-T, Luo W.-J, Ling F, Zhong W.-H. J. Chem. Res. 2018; 42: 579
      Crossref
    • 4c Hou C.-D, Ren Y.-L, Lang R, Hu X.-X, Xia C.-G, Li F.-W. Chem. Commun. 2012; 48: 5181
      CrossrefPubMed
    • 4d Felipe-Blanco D, Alonso F, Gonzalez-Gomez JC. Adv. Synth. Catal. 2017; 359: 2857
      Crossref
    • 5a Chun S, Yang S, Chung Y.-K. Tetrahedron 2017; 73: 3438
      Crossref
    • 5b Gao X, Yu B, Mei Q.-Q, Yang Z.-Z, Zhao Y.-F, Zhang H.-Y, Hao L.-D, Liu Z.-M. New J. Chem. 2016; 40: 8282
      Crossref
    • 5c Mostafavi H, Islami MR, Ghonchepour E, Tikdari AM. Chem. Papers 2018; 72: 2973
      Crossref
    • 5d Rasal KB, Yadav GD. Org. Process Res. Dev. 2016; 20: 2067
      Crossref
    • 6a Ke Z.-G, Yu B, Wang H, Xiang J.-F, Han J.-J, Wu Y.-Y, Liu Z.-H, Yang P, Liu Z.-M. Green Chem. 2019; 21: 1695
      Crossref
    • 6b Gao X, Yu B, Yang Z.-Z, Zhao Y.-F, Zhang H.-Y, Hao L.-D, Han B.-X, Liu Z.-M. ACS Catal. 2015; 5: 6648
      Crossref
    • 6c Song J.-L, Zhou B.-W, Liu H.-Z, Xie C, Meng Q.-L, Zhang Z.-R, Han B.-X. Green Chem. 2016; 18: 3956
      Crossref
    • 6d Zhang B, Du G.-X, Hang W, Wang S, Xi C.-J. Eur. J. Org. Chem. 2018; 1739
    • 7a Wade AR, Pawar HR, Biware MV, Chikate RC. Green Chem. 2015; 17: 3879
      Crossref
    • 7b Sharma H, Singh N, Jang DO. Green Chem. 2014; 16: 4922
      Crossref
    • 7c Samanta S, Das S, Biswas P. J. Org. Chem. 2013; 78: 11184
      CrossrefPubMed
    • 7d Sharma P, Gupta M, Kant R, Gupta VK. New J. Chem. 2015; 39: 5116
      Crossref
    • 8a Zhang G.-t, Yi H, Chen H, Bian C.-L, Liu C, Lei A.-W. Org. Lett. 2014; 16: 6156
      CrossrefPubMed
    • 8b Tan W, Wang C.-H, Jiang X.-F. Chin. J. Chem. 2019; 37: 1234
      Crossref
    • 8c Jin S.-N, Kuang Z.-J, Song Q.-L. Org. Lett. 2020; 22: 615
      CrossrefPubMed
    • 8d Ming W, Dai Z.-H, Jiang X.-F. Nat. Commun. 2019; 10: 2661
      CrossrefPubMed
    • 8e Wang M, Fan Q.-L, Jiang X.-F. Org. Lett. 2016; 18: 5756
      CrossrefPubMed
  • 9 Gu Z.-Y, Cao J.-J, Wang S.-Y, Ji S.-J. Chem. Sci. 2016; 7: 4067
    CrossrefPubMed
  • 10 Li J.-H, Huang Q, Wang S.-Y, Ji S.-J. Org. Lett. 2018; 20: 4704
    CrossrefPubMed
  • 11 Liu B.-B, Bai H.-W, Liu H, Wang S.-Y, Ji S.-J. J. Org. Chem. 2018; 83: 10281
    CrossrefPubMed
    • 12a Yoo E.-J, Chang S. Org. Lett. 2008; 10: 1163
    • 12b Liu M.-Y, Wang X, Sun X.-L, He W. Tetrahedron Lett. 2014; 55: 2711
      Crossref
    • 12c Reddy SM. K, Kothandapani J, Sengan K, Veerappan A, Selva GS. Mol. Catal. 2019; 465: 80
    • 12d Ramesh K, Satyanarayana G. Eur. J. Org. Chem. 2019; 3856
    • 12e Rong M.-G, Qin T.-Z, Zi W.-W. Org. Lett. 2019; 21: 5421
      CrossrefPubMed
    • 12f Xie C.-X, Han X.-S, Gong J, Li D.-Y, Ma C. Org. Biomol. Chem. 2017; 15: 5811
      CrossrefPubMed
    • 12g Caddick S, Kofie W. Tetrahedron Lett. 2002; 43: 9347
      Crossref
    • 12h Weinrich ML, Beck HP. Tetrahedron Lett. 2009; 50: 6968
      Crossref
    • 12i Lu C, Zhang Q, Chen X. Synth. Commun. 2016; 46: 1215
      Crossref