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

Brocklehurst, Cara and Koch, Guido and Makarov, Ilya S. and Karaghiosoff, Konstantin L. and Knochel, Paul (2017) Synthesis of Bicyclo[1.1.1]pentane Bioisosteres of Internal Alkynes and para-Disubstituted Benzenes from [1.1.1]Propellane. Angewandte Chemie International Edition.

Abstract

Abstract: We have reported a general preparation of arylated bicyclopentanes by the opening of [1.1.1]propellane with various arylmagnesium reagents. After transmetalation with ZnCl2 and a Negishi cross-coupling with aryl and heteroaryl halides, we have obtained bis-arylated bicyclopentanes which may be considered as bioisosteres of disubstituted alkynes such as tazarotene and the metabotropic glutamate receptor 5 (mGluR5) antagonist 2-methyl-6-(phenylethynyl)pyridine.

Item Type: Article
Date Deposited: 03 Oct 2017 00:45
Last Modified: 03 Oct 2017 00:45
URI: https://oak.novartis.com/id/eprint/32896

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