DIHYDRODIPYRIDOPYRAZINES: SYNTHESIS AND FUNCTIONALIZATION <br/> DIHYDRODIPYRIDOPYRAZINES: SYNTHESE ET FONCTIONNALISATION

STÉPHANIE BLANCHARD(1), IRINA GRIG-ALEXA(1 2), OANA-IRINA PATRICIU(1 2), ADRIANA FÎNARU(2), GÉRALD GUILLAUMET(1*)

(1)UNIVERSITÉ D’ORLÉANS, INSTITUT DE CHIMIE ORGANIQUE ET ANALYTIQUE, UMR CNRS 6005, BP 6759, RUE DE CHARTRES, 45067 ORLÉANS CEDEX 2, FRANCE
(2) UNIVERSITÉ « VASILE ALECSANDRI » DE BACĂU, LABORATOIRE DE SYNTHèSE ORGANIQUE ET ANALYSE STRUCTURALE,

Abstract

Different conceptual synthetic approaches to the elaboration of a new family of planar polynuclear nitrogen containing aromatic heterocycles – the dihydrodipyridopyrazines – are reviewed: the arynic reaction, the sequence palladium coupling reaction - substitution - reduction - cyclization - substitution or through the intermediacy of Smiles rearrangement. Further functionalization of these compounds by substitution reaction, metalation sequence and palladium-catalyzed coupling reaction are also discussed.

Keywords

dihydrodipyridopyrazines hetarynic cyclization Pd catalysis alkylation reduction cyclization Smiles rearrangement dipyridinylamines cross-coupling