Reaction of Blatter and Verdazyl Radicals with Arynes: Synthesis and Investigation of N-Chiral, Antiaromatic Triazines, and Tetrazinones.

ABSTRACT: Arynes are versatile building blocks in organic chemistry. In contrast to their extensively examined ionic reactivity, radical reactions with arynes remain scarcely explored. In this study, we present a novel radical annulation reaction of stable Blatter and verdazyl radicals with arynes, which offers access to polycyclic triazines and tetrazinones. The N2- and N4-annulated triazines derived from Blatter radicals exhibit distinct bending modes of the 8π-electron triazine ring, yet retain a certain degree of antiaromaticity despite their nonplanar geometries, as revealed by NICS and ACID calculations. Notably, the N2-annulated triazines feature a strongly pyramidalized nitrogen atom with N-chirality. Optical resolution yielded pure enantiomers, from which the configurational stability was a

SUBMITTER: Lezius L 

PROVIDER: S-EPMC12759216 | biostudies-literature | 2026 Jan

REPOSITORIES: biostudies-literature