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Biginelli and Hantzsch-Type Reactions Leading to Highly Functionalized Dihydropyrimidinone, Thiocoumarin, and Pyridopyrimidinone Frameworks via Ring Annulation with beta-Oxodithioesters

  作者 NANDI GANESH CHANDRA; SAMAI SUBHASIS; SINGH MAYA SHANKAR  
  选自 期刊  Journal of Organic Chemistry;  卷期  2010年75-22;  页码  7785-7795  
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[摘要]An efficient and highly convergent route to dihydropyrimidinones (DHPMs) and hitherto unreported dihydropyridopyrimidinones has been developed by one-pot, three-component cyclocondensation of aromatic aldehydes, beta-oxodithioesters, and urea/6-amino-1,3-dimethyluracil in the presence of recyclable SiO2-H2SO4 On the other hand, salicylaldehyde, beta-oxodithioester, and urea reacted under similar conditions to afford the 3-aroyl/heteroaroyl-2H-chromen-2-thiones in high yields instead of Biginelli product The attractive feature of this approach is the synthesis of three important bioactive heterocyclic frameworks from the same beta-oxodithioester under the similar reaction conditions, making this new strategy highly useful in diversity-oriented synthesis (DOS)

 
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