Logo Logo
Hilfe
Hilfe
Switch Language to English
Makarov, Ilya S.; Brocklehurst, Cara E.; Karaghiosoff, Konstantin; Koch, Guido; Knochel, Paul (2017): Synthesis of Bicyclo[1.1.1]pentane Bioisosteres of Internal Alkynes and para-Disubstituted Benzenes from [1.1.1]Propellane. In: Angewandte Chemie-international Edition, Vol. 56, Nr. 41: S. 12774-12777
Volltext auf 'Open Access LMU' nicht verfügbar.

Abstract

We report a general preparation of arylated bicyclo[1.1.1]pentanes through the opening of [1.1.1]propellane with various arylmagnesium halides. After transmetalation with ZnCl2 and Negishi cross-coupling with aryl and heteroaryl halides, bis-arylated bicyclo[1.1.1]pentanes are obtained. These bis-arylated bicyclo[1.1.1]pentanes may be considered as bioisosteres of internal alkynes. Bioisosteres of tazarotene and the metabotropic glutamate receptor 5 (mGluR5) antagonist 2-methyl-6-(phenylethynyl)pyridine were prepared and their physicochemical properties were evaluated.