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Synthesis 1997; 1997(12): 1461-1466
DOI: 10.1055/s-1997-1380
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Synthesis of 1,2,4-Triazole-Fused Heterocycles by Tandem Appel Dehydration/Thermal Rearrangement Methodology

Kee-Jung Lee1 , Seong Heon Kim2 , Jong Hyuk Kwon1
  • 1Department of Industrial Chemistry, Hanyang University, Seoul 133-791, South Korea
  • 2Division of Chemistry, Korea Institute of Science and Technology, P.O. Box 131, Seoul 130-650, South Korea
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Publication Date:
31 December 2000 (online)

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The reaction of α-substituted benzophenone 1-acetamidoethylidene-hydrazones 6b,c and 13a-d with a mixture of triphenylphosphine, carbon tetrachloride, and triethylamine in dichloromethane (Appel's condition) provides a general route to a variety of 1,2,4-triazole-fused heterocycles such as compounds 9-11, 16a-d, 17b-d, and 18 via the thermal rearrangement of the expected azino ketenimine intermediates.

1,2,4-triazole-fused heterocycle - tandem Appel dehydration-thermal rearrangement - azinoketenimine - benzophenone 1-amidoethylidenehydrazone - zwitterionic