Synthesis of 2-aryl-3-methylbenzo[<italic>g</italic>]indoles from 2-(arylethynyl)-1,8-bis(dimethylamino)naphthalenes: new examples of [1,3]-migration involving <italic>N</italic>-methyl group.

<graphic></graphic>The Sonogashira coupling of 1,8-bis(dimethylamino)-2-iodonaphthalene with 2-nitro-, 4-nitro-, 4-(trifluoromethyl)-, and 4-methoxyphenylacetylenes was used to obtain new 2-(arylethynyl)-1,8-bis(dimethylamino)naphthalenes. Three of the four alkynes, except for the <italic>o</italic>-nitrophenyl derivative, were isomerized in the presence of palladium and porcelain catalysis to the corresponding 2-aryl-9-(dimethylamino)-1,3-dimethyl-1<italic>H</italic>-benzo[<italic>g</italic>]indoles. [ABSTRACT FROM AUTHOR]