Domino Transformations of 3‐Fluoro‐1,2,4‐Triazine Derivatives towards Spirocyclic and Fused Pyridines

Abstract

A domino SNAr‐ihDA/rDA reaction was developed from rarely exploited 3‐fluoro‐1,2,4‐triazines with bifunctional alkyne tethered nucleophiles to construct various fused non‐aromatic/heteroaromatic bicycles in yields ranging from 56 to 99%, notably within the family of valuable spirooxindole derivatives. In this study, the challenging enantioselective phase‐transfer catalyzed arylation of a sulfonyl‐triazine was also demonstrated with up to 66% ee. In both racemic and asymmetric processes, the nature of the leaving group at C3 was key to successfully achieve these sequences.