Convenient Synthesis of 3H-Pyrrolo2,3-cIsoquinolines and 3-H-Pyrrolo2,3-c1,7-,3,4-Benzoc1,7-, and Dihydro-Pyrido4,3-c1,8Naphthyridines Via Palladium-Assisted Nucleophilic Amination

摘要

2-Methyl-and 3-ethyl-3H-pyrrolo2,3-cisoquinolines and 2-methyl-3H-pyrorlo2,3-c1,7naphthyridines possessing a C-5 saturated heterocyclic ring were prepared from corresponding 4-alkenyl-3-amino-isoqjuinoline or naphthylridinevia palladium-assised cyclization under catalytic conditions. Similar treatment of 3-prenyl derivatives of isoquinoloines and naphthyridines possessing 6-alkyl groups gave 3,3-dimetjhylo-3,4-di-hydrobenzoc- and 3,4-dihydropyridino4,3-cnaphthyridines, respectively. The Hegedus precursors were synthesized by alkenylation of 2-cyano-methylbenzonitrile or 3-cyanomethylpyridine-2-carbonitrile followed by base-mediated cyclization of #alpha#-alkenyl derivatives so formed using lithium amiades or alkyllithiums.