Synthesis of Bicyclo[1.1.1]pentane Bioisosteres of Internal Alkynes and  para ‐Disubstituted Benzenes from [1.1.1]Propellane | Zendy

Makarov Ilya S. | Zendy; Brocklehurst Cara E. | Zendy; Karaghiosoff Konstantin | Zendy; Koch Guido | Zendy; Knochel Paul | Zendy

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Synthesis of Bicyclo[1.1.1]pentane Bioisosteres of Internal Alkynes and para ‐Disubstituted Benzenes from [1.1.1]Propellane

Author(s) -

Makarov Ilya S.,

Brocklehurst Cara E.,

Karaghiosoff Konstantin,

Koch Guido,

Knochel Paul

Publication year - 2017

Publication title -

angewandte chemie international edition

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 5.831

H-Index - 550

eISSN - 1521-3773

pISSN - 1433-7851

DOI - 10.1002/anie.201706799

Subject(s) - bicyclic molecule , propellane , chemistry , pentane , pyridine , transmetalation , medicinal chemistry , stereochemistry , organic chemistry , catalysis

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 ZnCl 2 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.

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