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Toward Pyrrolo[2,3- d ]pyrimidine Scaffolds

2010; American Chemical Society; Volume: 75; Issue: 15 Linguagem: Inglês

10.1021/jo100759b

1520-6904

Laurent El Kaïm, Laurence Grimaud, Simon Wagschal,

Catalytic Cross-Coupling Reactions

Herein, we present a new route to highly substituted pyrrolo[2,3-d]pyrimidines featuring a Ugi-Smiles/Sonogashira cascade followed by an efficient base-catalyzed intramolecular cyclization. When formaldehyde is chosen as input in the Ugi-Smiles step, aromatic fused systems are eventually obtained through the isomerization of an exo-alkylidene intermediate.