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3Â¥2011-06-03 17:40:36
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putin092910(½ð±Ò+3): 2011-06-04 13:07:04
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¸øÄã¸ö²Î¿¼°É£¡ Significance of the work Biginelli reaction is an important organic transformation for the synthesis of dihydropyrimidinones compounds which exhibit a wide range of biological activities such as antiviral, antitumor, antibacterial and antiflammatory properties. The one-pot reaction usually proceeds well in the presence of Lewis acids or protic acids. Just as Biginelli reaction which operates in the presence of Lewis acid or protic acid, those multi-component reactions for the preparation of new dihydropyrimidinones using various active methylene compounds instead of acetoacetate derivatives, such as such as 5,5-dimethyl-1,3-cyclohexanedione, 1,3-cyclohexanedione, 1-tetralone, acetophenone, cyclopentanone, aliphatic aldehydes and-oxodithioesters are also carried out using Lewis acid or protic acid such as HCl, TMSCl/NaI, FeCl3 and YbCl3. However, till now, there is no report on the development of one-pot Biginelli-type reaction under basic conditions. In addition, there are few studies on the mechanism of Biginelli reaction. We envisioned that if the Biginelli-type reaction can be developed to carry out under basic conditions using Brönsted bases rather than Lewis acids it will provide an attractive alternative to existing methodologies and help deepen our understanding of Biginelli reaction. In this report, we describe a novel Brönsted base-promoted one-pot synthesis of 3,4-dihydropyrimidin-2(1H)-one via a three-component condensation of aldehyde, 2-phenylacetophenone, and urea or thiourea. The reactions proceeded efficiently in the presence of a catalytic amount of Brönsted bases (20 mol% t-BuOK) to afford dihydropyrimidinone compounds in moderate to good yields. The method is simple, convenient, efficient, and expects to be a useful synthetic protocol for the synthesis of a wide range of novel drug-like dihydropyrimidinone compounds. In addition, a detailed mechanistic study was carried out. It was interesting to observe that the reactions with the use of thiourea as substrate proceeds via intermediate enone 5; whereas, the use of urea as substrate occurred via bis-urea compound 8. We forecast that the use of bisurea 8 as substrate for the synthesis of 3,4-dihydropyrimidin-2(1H)-one will gain popularity in future. To the best of our knowledge, this is the first Brönsted base-promoted one-pot approach for the synthesis of Biginelli-like scaffold compounds of dihydropyrimidinones. In addition, it was the first observation that the Biginelli-type reaction using urea or thiourea proceeds through two different pathways. Compared with commonly employed methods for the preparation of dihydropyrimidinones using Lewis acid or protic acid, the methodology presented herein provided a novel, convenient, efficient and cheap access to new dihydropyrimidinones in a one-pot manner. As such, this paper deserves to be published as a Communication in chemical communications, in view of potent synthetic value associated with this method and its potential to draw the attention of many readers of chemical communications. |
4Â¥2011-06-03 17:47:35














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