Tetracyanoethylene as a Building Block in the π-Expansion of 1,4-Dihydropyrrolo[3,2-<i>b</i>]pyrroles.

ABSTRACT: The outcome of the reaction of tetracyanoethylene with 1,4-dihydropyrrolo[3,2-b]pyrroles (DHPPs) strongly depends on the character of the substituents present at positions 2 and 5. With electron-withdrawing substituents, the reaction does not occur at all, while, in contrast, the presence of electron-donating substituents yields addition-elimination products. When thiazol-2-yl substituents are located at positions 2 and 5, addition occurs at the thiazole ring, rather than of the DHPP core. In cases where very electron-rich heterocycles are present at positions 2 and 5, a second addition occurs followed by aromatization, leading to the formation of an additional benzene ring bridging two heterocyclic scaffolds. The reaction occurs only at one site since the presence of the strongly e

SUBMITTER: Erdemir GY 

PROVIDER: S-EPMC11536355 | biostudies-literature | 2024 Nov

REPOSITORIES: biostudies-literature