A new access to 4 H-quinolizines from 2-vinylpyridine and alkynes promoted by rhodium-N-heterocyclic-carbene catalysts.

Ramón Azpíroz, Andrea Di Giuseppe, Ricardo Castarlenas, Jesús J Pérez-Torrente, Luis A Oro

Departamento Química Inorgánica, Instituto Síntesis Química y Catálisis Homogénea, Universidad de Zaragoza-CSIC, Pl. S. Francisco S/N 50009 Zaragoza, Spain.

Chemistry (Weinheim an der Bergstrasse, Germany) 2013 Mar 18

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Forging the lock that autolocks! Rh-NHC catalysts promote a new access to 4 H-quinolizine species from 2-vinylpyridine and terminal and internal alkynes through C-H activation and C-C coupling reactions (see figure). N-Bridgehead heterocycle formation is favored for internal- over terminal-substituted butadienylpyridine derivatives in a thermal 6π-electrocyclization process. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Citation

Ramón Azpíroz, Andrea Di Giuseppe, Ricardo Castarlenas, Jesús J Pérez-Torrente, Luis A Oro. A new access to 4 H-quinolizines from 2-vinylpyridine and alkynes promoted by rhodium-N-heterocyclic-carbene catalysts. Chemistry (Weinheim an der Bergstrasse, Germany). 2013 Mar 18;19(12):3812-6