CF2-Containing acetylenephosphonates in heterocyclization reactions: the first synthesis of 2-difluoromethyl azaxanth-3-ylphosphonates

Blazej Duda; Sergey N. Tverdomed; Gerd-Volker Röschenthaler

doi:10.1039/C1OB06379K

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CF₂-Containing acetylenephosphonates in heterocyclization reactions: the first synthesis of 2-difluoromethyl azaxanth-3-ylphosphonates†

Blazej Duda,^a Sergey N. Tverdomed*^a and Gerd-Volker Röschenthaler*^a

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* Corresponding authors

^a School of Engineering and Science, Jacobs University Bremen, Campus Ring 1, Germany
E-mail: s.tverdomed@jacosb-university.de, g.roeschenthaler@jacobs-university.de
Fax: +49 421 200 3229
Tel: +49 421 200 3138

Abstract

Acetylenephosphonates carrying the XCF₂ group have been studied in a base-mediated heterocyclization reaction with selected 2-amino-3-formylchromones to give 2-difluoromethyl azaxanth-3-ylphosphonates. The presence of the fluorinated substituent determined the regioselectivity as well as the reactivity of this process.

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Article information

DOI: https://doi.org/10.1039/C1OB06379K
Article type: Communication
Submitted: 12 Aug 2011
Accepted: 28 Sep 2011
First published: 19 Oct 2011

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Org. Biomol. Chem., 2011,9, 8228-8232

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CF₂-Containing acetylenephosphonates in heterocyclization reactions: the first synthesis of 2-difluoromethyl azaxanth-3-ylphosphonates

B. Duda, S. N. Tverdomed and G. Röschenthaler, Org. Biomol. Chem., 2011, 9, 8228 DOI: 10.1039/C1OB06379K

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Organic & Biomolecular Chemistry