4.7 Article

N-Heterocyclic Carbene-Catalyzed in situ Activation of Alkynyl Acids for C-S Bond Formation: Access to Imidazo[2,1-b][1,3]thiazinones

Journal

ADVANCED SYNTHESIS & CATALYSIS
Volume 360, Issue 23, Pages 4515-4522

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201800857

Keywords

carbene; alkynyl acid; in situ activation; C-S bond formation; heterocyclic compounds

Funding

  1. National Natural Science Foundation of China [21572270]
  2. Qing Lan Project of Jiangsu Province
  3. Priority Academic Program Development of Jiangsu Higher Education Institutions
  4. College Students Innovation Project for the R&D of Novel Drugs [J1310032]

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Alkynyl acids are first utilized as alkynyl acylazolium precursors through an in situ activation strategy for the efficient construction of carbon-sulfur bond in a formal [3+3] annulation. This protocol offers a direct and rapid pathway for the synthesis of imidazo[2,1-b][1,3]thiazinone skeleton, a useful heterocyclic class frequently found in many bioactive compounds. This reaction also has the advantages of scalability, readily available materials, and simple manipulation in open air.

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