A convenient, high-yield synthesis of 1-substituted uracil and thymine derivatives
Novel reagents for the synthesis of 1-substituted uracil and thymine derivatives have been developed. The aminolysis of 2- or 4-nitrophenyl 3-ethoxyacryloylcarbamate and 3-ethoxy-2-methylacryloylcarbamate with a variety of primary amino derivatives procee
Rejman, Dominik,Kova?ková, Soňa,Pohl, Radek,Dra?ínsky, Martin,Fiedler, Pavel,Rosenberg, Ivan
experimental part
p. 8513 - 8523
(2010/01/06)
Straightforward pyrimidine ring construction: A versatile tool for the synthesis of nucleobase and nucleoside analogues
A general route to 1,2,4-trisubstituted pyrimidines is described in one to three steps from a common key precursor, diazadienium iodide 2. An efficient preliminary [4+2] cyclocondensation reaction between the azabutadiene building block 2 and various iso(thio)cyanates constitutes an original construction of the pyrimidine skeleton. Subsequent structural modifications on the heterocycle allow the elaboration of a 1-substituted pyrimidine library that includes nucleoside analogues. Wiley-VCH Verlag GmbH & Co. KGaA, 2006.
Robin, Aelig,Julienne, Karine,Meslin, Jean-Claude,Deniaud, David