Synthesis and Physicochemical Properties of 2-SF₅-(Aza)Indoles, a New Family of SF₅ Heterocycles.

ABSTRACT: Structural diversity in heterocyclic chemistry is key to unlocking new properties and modes of action. In this regard, heterocycles embedding emerging fluorinated substituents hold great promise. Herein is described a strategy to access 2-SF₅-(aza)indoles for the first time. The sequence relies on the radical addition of SF₅Cl to the alkynyl π-system of 2-ethynyl anilines followed by a cyclization reaction. A telescoped sequence is proposed, making this strategy very appealing and reproducible on a gram scale. Downstream functionalizations are also demonstrated, allowing an easy diversification of N- and C3-positions. Ames test, pK _a, log P, and differential scanning calorimetry measurements of several fluorinated 2-Rf-indoles are also disclos

SUBMITTER: Debrauwer V 

PROVIDER: S-EPMC9954346 | biostudies-literature | 2021 Dec

REPOSITORIES: biostudies-literature