Synthesis and reactivity of nitrogen-containing strained cyclic 1,2,3-trienes.

ABSTRACT: Cyclic 1,2,3-trienes are a class of intermediates that confine a functional group with a preferred linear geometry into a ring. When the ring is sufficiently small, the 1,2,3-triene geometry becomes bent, leading to substantial strain and high reactivity. Whereas advances in cyclic 1,2,3-triene chemistry have focused on carbocyclic derivatives, the corresponding chemistry of their heteroatom-containing counterparts remains unexplored. Here we report the fluoride-mediated generation and trapping of six-membered azacyclic 1,2,3-trienes in a host of reactions, including (4 + 2) and (3 + 2) cycloadditions and σ-bond insertions, allowing for the synthesis of annulated pyridones. Moreover, computational studies provide insight into their structure and reactivity. This study pushes the lim

SUBMITTER: Witkowski DC 

PROVIDER: S-EPMC12459638 | biostudies-literature | 2025 Aug

REPOSITORIES: biostudies-literature