Biginelli and Hantzsch-Type Reactions Leading to Highly Functionalized Dihydropyrimidinone, Thiocoumarin, and Pyridopyrimidinone Frameworks via Ring Annulation with β-Oxodithioesters
详细信息 查看全文
- 作者：Ganesh Chandra Nandi ; Subhasis Samai ; Maya Shankar Singh
- 刊名：Journal of Organic Chemistry
- 出版年：2010
- 出版时间：November 19, 2010
- 年：2010
- 卷：75
- 期：22
- 页码：7785-7795
- 全文大小：1074K
- 年卷期：v.75,no.22(November 19, 2010)
- ISSN：1520-6904
文摘
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, β-oxodithioesters, and urea/6-amino-1,3-dimethyluracil in the presence of recyclable SiO2−H2SO4. On the other hand, salicylaldehyde, β-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 β-oxodithioester under the similar reaction conditions, making this new strategy highly useful in diversity-oriented synthesis (DOS).