4.8 Article

A Three-Component Approach to 3,5-Diaryl-1,2,4-thiadiazoles under Transition-Metal-Free Conditions

Journal

ORGANIC LETTERS
Volume 18, Issue 9, Pages 2196-2199

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.6b00806

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Funding

  1. National Natural Science Foundation of China [21372187, 21572194, 21502160]
  2. Program for Innovative Research Cultivation Team in University of Ministry of Education of China [1337304]
  3. Hunan Provincial Innovative Foundation for Postgraduate [CX2015B202]

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A novel route is disclosed for the synthesis of 1,2,4-thiadiazoles starting from amidines, elemental sulfur, and 2-methylquinolines or aldehydes under transition-metal-free conditions. This three-component approach affords efficient and rapid access to 3,5-diaryl substituted 1,2,4-thiadiazoles with good tolerance of a broad range of funcitional groups. Mechanistic studies reveal a radical-involved pathway.

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