Synthesis and biological evaluation of 5-(alkyn-1-yl)-1-(p-toluenesulfonyl) uracil derivatives

Z Janeba, J Balzarini, G Andrei…

Index: Janeba, Zlatko; Balzarini, Jan; Andrei, Graciela; Snoeck, Robert; De Clercq, Erik; Robins, Morris J. Canadian Journal of Chemistry, 2006 , vol. 84, # 4 p. 580 - 586

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Citation Number: 14

Abstract

Sonogashira coupling of 5-iodouracil (2) and trimethylsilylacetylene gave 5- (trimethylsilylethynyl) uracil (3), which was deprotected to give 5-ethynyluracil (4). Copper (I)- catalyzed cyclization of 4 gave furo [2, 3-d] pyrimidin-2 (3 H)-one (5). Tosylation of 2 and 4 gave the 1-(p-toluenesulfonyl) derivatives 6 and 7, respectively. The tosylated compound 6 and trimethylsilylacetylene did not undergo Sonogashira coupling, and copper (I)- ...