T. Steinlin, Tiziana Sonati, A. Vasella
Oct 1, 2008
Citations
0
Influential Citations
7
Citations
Journal
Helvetica Chimica Acta
Abstract
Intramolecular condensation of the N-(4-amino-5-nitrosopyrimidin-4-yl)-2-chloroacetamide 2 led to the pteridinone N(5)-oxide 4, while treatment of 2 with Me3P yielded the 8-(chloromethyl)purine 3. A high-yielding [3+2] dipolar cycloaddition of the N(5)-oxide 4 to electron-poor dipolarophiles, followed by spontaneous N,O-bond cleavage, gave the C(6)-substituted pteridinones 8a–8d that were deprotected to provide the pteridine-4,7(3H,8H)-diones 9a–9d, constituting a new synthesis of pterinones possessing a functionalised side chain at C(6).