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Paper | Special issue | Vol 56, No. 1-2, 2002, pp.443-455
Published online, 1st January, 1970
DOI: 10.3987/COM-01-S(K)68
Convenient Synthesis of 3H-Pyrrolo[2,3-c]isoquinolines and 3H-Pyrrolo[2,3-c][1,7]-, 3,4-Benzo[c][1,7]-, and Dihydropyrido[4,3-c][1,8]naphthyridines via Palladium-assisted Nucleophilic Amination

U. Narasimha Rao and Edward R. Biehl*

*Chemistry Department, Southern Methodist University, Dallas, TX 75275, U.S.A.

Abstract

2-Methyl- and 3-ethyl-3H-pyrrolo[2,3-c]isoquinolines and 2-methyl-3H-pyrrolo[2,3-c][1,7]naphthyridines possessing a C-5 saturated heterocyclic ring were prepared from corresponding 4-alkenyl-3-aminoisoquinoline or naphthyridinevia palladium-assisted cyclization under catalytic conditions. Similar treatment of 3-prenyl derivatives of isoquinolines and naphthyridines possessing 6- alkyl groups gave 3,3,-dimethyl-3,4-dihydrobenzo[c]- and 3,4-dihydropyridino[4,3-c]naphthyridines, respectively. The Hegedus precursors were synthesized by alkenylation of 2-cyanomethylbenzonitrile or 3-cyanomethylpyridine-2-carbonitrile followed by basemediated cyclization of α-alkenyl derivatives so formed using lithium amides or alkyllithiums.