A practical and efficient synthesis of 2,5-disubstituted-3,5-dihydro- imidazol-4-ones from oxazolones
An alternative procedure for the synthesis of 2,5-disubstituted-3,5- dihydro-imidazol-4-ones from substituted oxazolones was evaluated. The initial oxazolone ring-opening reaction was examined with a variety of ammonia source compounds followed by the sub
Chavez, Flavio,Pavy, Caslin,Williamson, Thomas,Cleary, Thomas
experimental part
p. 3321 - 3327
(2012/09/21)
Simple and efficient copper-catalyzed approach to 2,4-disubstituted imidazolones
(Figure Presented) Some imidazolone derivatives are biological and pharmaceutical active molecules and the chromophores of the fluorescent proteins. In this communication, a simple and efficient approach to 4-arylidene-2-alkyl-4,5-dihydro-1H-imidazol-5-ones (2,4-disubstituted imidazolones) has been developed, and the protocol uses readily available 2-bromo-3-alkylacrylic acids and amidines as the starting materials without addition of any ligand or additive. The reactions were performed under mild conditions. Therefore, the present method will be of wide application in organic chemistry and medicinal chemistry.
A Convenient Synthesis of Unsaturated 2,4-Disubstituted 2-Imidazolin-5-ones
Twenty five unsaturated 2,4-disubstituted 2-imidazolin-5-ones (IV) have been prepared in 23-71percent yields by condensing aromatic aldehydes with a mixture of ethyl chloroacetate and an aromatic amidinium chloride in the presence of sodium hydrogencarbonate.Twenty three of them have also been prepared in 62-97percent yields by this method using ethyl bromoacetate instaed of the chloroacetate.Further, two unsaturated 2-imidazolin-5-ones (IV) have been prepared by these two methods using cyclohexanone (yields 33percent each) and cinnamaldehyde (yields 0 and 18percent) instead of the aromatic aldehydes.
Devasia, Ganapathiplackal M.,Shafi, P. Mohamed
p. 657 - 660
(2007/10/02)
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