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Communication | Regular issue | Vol 68, No. 7, 2006, pp.1325-1328
Published online, 30th May, 2006
DOI: 10.3987/COM-06-10727
Synthesis of N1-Unsubstituted 5-Alkynylcytosine and Derivatives Thereof

Robert H. E. Hudson* and Andrew K. Dambenieks

*Department of Chemistry, University of Western Ontario, London, Ontario, N6A5B7, Canada

Abstract

The first examples of 5-alkynylcytosines (3) lacking other ring substitution have been synthesized directly from Sonogashira coupling of 5-iodocytsoine (1) with terminal alkynes. Alternatively, 7H-pyrrolo[2,3-d]pyrimidin-2(H)-ones (4), via domino cross-coupling and cyclization reactions were prepared from N4-benzoyl-5-iodocytosine (2). Both the 5-phenylethynylcytosines and bicyclic derivatives show substituent-dependent fluorescence.