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New Synthesis and Reactivity of 3-Bromoacetyl-4-hydroxy-6-methyl-2H-pyran-2-one with Binucleophilic Amines

  作者 HIKEMOUKACHA DJAMILA; HAMDI MAAMAR; SILVA ARTUR M S; YAHIA RACHEDI  
  选自 期刊  Journal of Heterocyclic Chemistry;  卷期  2011年48-1;  页码  63-73  
  关联知识点  
 

[摘要]3-(Bromoacetyl)-4-hydroxy-6-methyl-2H-pyran-2-one was synthesized by the reaction of dehydroacetic acid (DHAA) with bromine in glacial acetic acid. Novel heterocyclic products were synthesized from the reaction of bromo-DHAA with alkanediamines, phenylhydrazines, ortho-phenylenediamines, and ortho-aminobenzenethiol. The obtained new products 3-(2-N-substituted-acetyl)-4-hydroxy-6-methyl-2H-pyran-2-ones, 4-hydroxy-3-[1-hydroxy-2-(2-phenylhydrazinyl)vinyl]-6-methyl-2H-pyran-2- one, 1-(2,4-dinitrophenyl)-7-methyl-2,3-dihydro-1H-pyrano[4,3-c]pyridazine-4, 5-dione, 3-(3,4-dihydroquinoxalin-2-yl)-4-hydroxy-6-methyl-2H-pyran-2-one/3-(3,4- dihydroquinoxalin-2-yl)-6-methyl-2H-pyran-2,4(3H)-dione, 6-methyl-3-(3,4-dihydroquinoxalin-2-yl)-2H-pyran-2,4(3H)-dione, and (E)-3-(2H-benzo[b][1,4]thiazin-3(4H)-ylidene)-6-methyl-2H-pyran-2,4(3H)- dione were fully characterized by IR, H-1 and C-13 NMR, and mass spectra.

 
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