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

Nandi, Ganesh Chandra ; Samai, Subhasis ; Singh, Maya Shankar (2010) Biginelli and Hantzsch-Type Reactions Leading to Highly Functionalized Dihydropyrimidinone, Thiocoumarin, and Pyridopyrimidinone Frameworks via Ring Annulation with β-Oxodithioesters Journal of Organic Chemistry, 75 (22). pp. 7785-7795. ISSN 0022-3263

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Official URL: http://doi.org/10.1021/jo101572c

Related URL: http://dx.doi.org/10.1021/jo101572c

Abstract

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).

Item Type:Article
Source:Copyright of this article belongs to American Chemical Society.
ID Code:119666
Deposited On:16 Jun 2021 05:54
Last Modified:16 Jun 2021 05:54

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