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Article Dans Une Revue ACS Organic & Inorganic Au Année : 2021

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

Résumé

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, pKa , log P, and differential scanning calorimetry measurements of several fluorinated 2-Rf-indoles are also disclosed. These studies highlight the strategic advantages that a C2-pentafluorosulfanylated motif impart to a privileged scaffold such as an indole.
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Dates et versions

hal-03357583 , version 1 (28-09-2021)

Identifiants

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Vincent Bizet, Vincent Debrauwer, Ivo Leito, Märt Lokov, Sofja Tshepelevitsh, et al.. Synthesis and Physicochemical Properties of 2-SF5-(Aza)Indoles, a New Family of SF5 Heterocycles. ACS Organic & Inorganic Au, In press, ⟨10.1021/acsorginorgau.1c00010⟩. ⟨hal-03357583⟩
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