Synthesis of 1-alkoxy-1,2,3,4-tetra-hydrocarbazoles by mercury(II) mediated heterocyclization of 2-cyclohex-2′-enyl-N-alkylanilines

Abstract

The title compounds 3(a–i) were synthesized in high yields by the mercury(II) mediated heterocyclization of 2-cyclohex-2′-enyl-N-alkylanilines 2(a–g), which in turn were obtained by the acid-catalyzed amino Claisen rearrangement of 3-N-alkylanilinocyclohexenes 1(a–g). Additional supporting evidence for the structure of product 3 was obtained from chemical transformations. Key words: 1-alkoxy tetrahydrocarbazole, mercury(II) mediated heterocyclization, amino Claisen rearrangement, 3-N-methylanilinocyclohexene.