Flavonoids-38. Reaction of 2'-hydroxychalcone dibromides and -α-bromochalcones with azide ion

Tamás Patonay, Rezsö Bognár, György Litkei

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Abstract

The reaction of 2'-hydroxychalcone dibromides 1 or α-bromo-2'-hydroxychalcones 15 with sodium azide resulted in a mixture of α-azido-2'-hydroxychalcones 2, 3-aryl-5-(2-hydroxy-pheny)isoxazoles 3, flavones 4, aurones 5 and 4-aryl-5-(2-hydroxybenzoyl)-1,2,3-triazoles 6. The product ratio was strongly influenced by the character of the substituent at position C-4. Similar results were obtained with 2'-benzyloxy-4-nitrochalcone dibromide (10) and 2'-benzyloxy-α-bromo-4-mtrochalcone (17). The mechanism of the transformation of chalcone dibromides into the products via an α-bromochalcone intermediate is discussed.

Original languageEnglish
Pages (from-to)2555-2562
Number of pages8
JournalTetrahedron
Volume40
Issue number13
DOIs
Publication statusPublished - 1984

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ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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