Synlett 2015; 26(20): 2811-2816
DOI: 10.1055/s-0035-1560496
cluster
© Georg Thieme Verlag Stuttgart · New York

Azine and Diazine Functionalization Using 2,2,6,6-Tetramethylpiperidino-Based Lithium–Metal Combinations: Application to the Synthesis of 5,9-Disubstituted Pyrido[3′,2′:4,5]pyrrolo[1,2-c]pyrimidines

Nada Marquise
a  Equipe Chimie et Photonique Moléculaires, Institut des Sciences Chimiques de Rennes, UMR 6226, CNRS-Université de Rennes 1, Bâtiment 10A, Case 1003, Campus de Beaulieu, 35042 Rennes, France   Email: florence.mongin@univ-rennes1.fr
,
Tan Tai Nguyen
a  Equipe Chimie et Photonique Moléculaires, Institut des Sciences Chimiques de Rennes, UMR 6226, CNRS-Université de Rennes 1, Bâtiment 10A, Case 1003, Campus de Beaulieu, 35042 Rennes, France   Email: florence.mongin@univ-rennes1.fr
,
Floris Chevallier
a  Equipe Chimie et Photonique Moléculaires, Institut des Sciences Chimiques de Rennes, UMR 6226, CNRS-Université de Rennes 1, Bâtiment 10A, Case 1003, Campus de Beaulieu, 35042 Rennes, France   Email: florence.mongin@univ-rennes1.fr
,
Laurent Picot
b  Laboratoire Littoral Environnement et Sociétés, UMRi CNRS 7266, Université de La Rochelle, 17042 La Rochelle, France   Email: valerie.thiery@univ-lr.fr
,
Valérie Thiéry*
b  Laboratoire Littoral Environnement et Sociétés, UMRi CNRS 7266, Université de La Rochelle, 17042 La Rochelle, France   Email: valerie.thiery@univ-lr.fr
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Olivier Lozach
c  USR 3151, CNRS-Université Pierre et Marie Curie, Kinase Inhibitor Specialized Screening Facility, KISSf, Station Biologique, 29680 Roscoff, France   Email: bach@sb-roscoff.fr
,
Stéphane Bach*
c  USR 3151, CNRS-Université Pierre et Marie Curie, Kinase Inhibitor Specialized Screening Facility, KISSf, Station Biologique, 29680 Roscoff, France   Email: bach@sb-roscoff.fr
,
Sandrine Ruchaud
c  USR 3151, CNRS-Université Pierre et Marie Curie, Kinase Inhibitor Specialized Screening Facility, KISSf, Station Biologique, 29680 Roscoff, France   Email: bach@sb-roscoff.fr
,
Florence Mongin*
a  Equipe Chimie et Photonique Moléculaires, Institut des Sciences Chimiques de Rennes, UMR 6226, CNRS-Université de Rennes 1, Bâtiment 10A, Case 1003, Campus de Beaulieu, 35042 Rennes, France   Email: florence.mongin@univ-rennes1.fr
› Author Affiliations
Further Information

Publication History

Received: 09 July 2015

Accepted after revision: 18 September 2015

Publication Date:
30 September 2015 (online)


Abstract

The synthesis of triaryl methanols was investigated by reacting different 4-metalated 2-substituted pyrimidines with diaryl ketones, the latter being generated by deprotocupration–aroylation of azine and diazine substrates. Cyclization of the triaryl methanols thus obtained afforded pyrido[3′,2′:4,5]pyrrolo[1,2-c]pyrimidines, which were evaluated for kinase inhibition and antiproliferative activities in melanoma cells.

Supporting Information

 
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