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Synthesis of 3-Substituted Aryl[4,5]isothiazoles through an All-Heteroatom Wittig-Equivalent Process

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College of Chemistry and Chemical Engineering, Shanghai University of Engineering Science, 333 Longteng Road, Shanghai 201620, China
Department of Biochemistry, University of Washington, 1705 NE Pacific Street, Seattle, Washington 98195, United States
Cite this: Org. Lett. 2016, 18, 11, 2777–2779
Publication Date (Web):May 24, 2016
https://doi.org/10.1021/acs.orglett.6b01338
Copyright © 2016 American Chemical Society
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Abstract

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Extending the previous use of tert-butyl sulfoxide as the sulfinyl source, intramolecular sulfinylation of sulfonamides was successfully performed. The resulting sulfinimides were not isolated and instead were believed to go through an all-heteroatom Wittig-equivalent process to eventually afford aryl[4,5]isothiazoles in high yields.

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The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acs.orglett.6b01338.

  • Procedures and characterization data for all new compounds (PDF)

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Cited By

This article is cited by 17 publications.

  1. Sanghun Moon, Yuji Nishii, Masahiro Miura. Synthesis of Isothiazoles and Isoselenazoles through Rhodium-Catalyzed Oxidative Annulation with Elemental Sulfur and Selenium. Organic Letters 2021, 23 (1) , 49-53. https://doi.org/10.1021/acs.orglett.0c03674
  2. Bei-Bei Liu, Hui-Wen Bai, Huan Liu, Shun-Yi Wang, Shun-Jun Ji. Cascade Trisulfur Radical Anion (S3•–) Addition/Electron Detosylation Process for the Synthesis of 1,2,3-Thiadiazoles and Isothiazoles. The Journal of Organic Chemistry 2018, 83 (17) , 10281-10288. https://doi.org/10.1021/acs.joc.8b01450
  3. Shengfeng Wu, Xiaofang Lei, Erkang Fan, and Zhihua Sun . Thermolysis-Induced Two- or Multicomponent Tandem Reactions Involving Isocyanides and Sulfenic-Acid-Generating Sulfoxides: Access to Diverse Sulfur-Containing Functional Scaffolds. Organic Letters 2018, 20 (3) , 522-525. https://doi.org/10.1021/acs.orglett.7b03593
  4. Boram Seo, Ya Gob Kim, and Phil Ho Lee . Synthesis of Isothiazole via the Rhodium-Catalyzed Transannulation of 1,2,3-Thiadiazoles with Nitriles. Organic Letters 2016, 18 (19) , 5050-5053. https://doi.org/10.1021/acs.orglett.6b02499
  5. Anirban Bera, Prasanta Patra, Abulkalam Azad, Sk Asraf Ali, Susanta Kumar Manna, Amit Saha, Shubhankar Samanta. Neat synthesis of isothiazole compounds, and studies on their synthetic applications and photophysical properties. New Journal of Chemistry 2022, 46 (24) , 11685-11694. https://doi.org/10.1039/D2NJ01962K
  6. Deepak R. Mishra, Bhabani S. Panda, Sabita Nayak, Jasmine Panda, Seetaram Mohapatra. Recent Advances in the Synthesis of 5‐Membered N ‐Heterocycles via Rhodium Catalysed Cascade Reactions. ChemistrySelect 2022, 7 (22) https://doi.org/10.1002/slct.202200531
  7. Min Wang, Xia Meng, Changqun Cai, Lingyun Wang, Hang Gong. Synthesis of benzisothiazoles by a three-component reaction using elemental sulfur and ammonium as heteroatom components under transition metal-free conditions. Green Synthesis and Catalysis 2022, 3 (2) , 168-174. https://doi.org/10.1016/j.gresc.2022.03.005
  8. V.I. Potkin, A.V. Kletskov, F.I. Zubkov. Isothiazoles. 2022, 482-529. https://doi.org/10.1016/B978-0-12-818655-8.00127-X
  9. Shaomin Chen, Rongxian Bai, Minghao Li, Ping Liu, Yanlong Gu. Acid‐Acid‐Catalyzed Tandem Reactions Driven by an Additive‐Like Component. The Chemical Record 2021, 21 (1) , 87-115. https://doi.org/10.1002/tcr.202000097
  10. Rose Mary Philip, Sankaran Radhika, P. V. Saranya, Gopinathan Anilkumar. Applications of tert -butanesulfinamide in the synthesis of N-heterocycles via sulfinimines. RSC Advances 2020, 10 (69) , 42441-42456. https://doi.org/10.1039/D0RA08819F
  11. María Jesús Cabrera-Afonso, Sara Cembellín, Adnane Halima-Salem, Mateo Berton, Leyre Marzo, Abdellah Miloudi, M. Carmen Maestro, José Alemán. Metal-free visible light-promoted synthesis of isothiazoles: a catalytic approach for N–S bond formation from iminyl radicals under batch and flow conditions. Green Chemistry 2020, 22 (20) , 6792-6797. https://doi.org/10.1039/D0GC02618B
  12. Francesca Mangiavacchi, Letizia Crociani, Luca Sancineto, Francesca Marini, Claudio Santi. Continuous Bioinspired Oxidation of Sulfides. Molecules 2020, 25 (11) , 2711. https://doi.org/10.3390/molecules25112711
  13. Tatiana V. Lyubchuk, Olga V. Hordiyenko. The use of N-halosuccinimides for cyclization with the formation of five-membered heterocyclic compounds. Chemistry of Heterocyclic Compounds 2020, 56 (1) , 1-29. https://doi.org/10.1007/s10593-020-02616-5
  14. Ana De Oliveira Silva, James McQuade, Michal Szostak. Recent Advances in the Synthesis and Reactivity of Isothiazoles. Advanced Synthesis & Catalysis 2019, 361 (13) , 3050-3067. https://doi.org/10.1002/adsc.201900072
  15. Dominic C. Castell, Ntlama Lesotho, Varvara I. Nikolayenko, Gareth E. Arnott. Inherently Chiral Calix[4]arenes: A Chiral Sulfoxide as an Ortholithiation Director. European Journal of Organic Chemistry 2017, 2017 (29) , 4328-4333. https://doi.org/10.1002/ejoc.201700701
  16. Yuan Chen, Fanghui Xu, Zhihua Sun. Synthesis of 1,2-disubstituted benzimidazoles using an aza-Wittig-equivalent process. RSC Advances 2017, 7 (70) , 44421-44425. https://doi.org/10.1039/C7RA09010B
  17. Fanghui Xu, Yuan Chen, Erkang Fan, Zhihua Sun. ChemInform Abstract: Synthesis of 3-Substituted Aryl[4,5]isothiazoles Through an All-Heteroatom Wittig-Equivalent Process.. ChemInform 2016, 47 (42) https://doi.org/10.1002/chin.201642145

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