Interrupted Intramolecular Hydroaminomethylation of <i>N</i>-Protected-2-vinyl Anilines: Novel Access to 3-Substitued Indoles or Indoline-2-ols

Abstract

A new synthetic alternative to the synthesis of 3-methyl indoles and 3-methyl indoline-2-ols with an excellent atomic economy is presented in this study. It is demonstrated that the intramolecular interrupted hydroaminomethylation (HAM) reaction is a powerful tool for the formation of these compounds, which exhibit wide-ranging biological activity. Several N-Protected-2-vinyl anilines were synthesized and involved in the reaction producing the corresponding 3-methylindole or 3-methyl indoline-2-ol depending on the nature of the N-protecting groups.

Keywords

• interrupted hydroaminomethylation
• indole
• indoline-2-ol
• <i>N</i>-protecting-2-vinyl aniline carbonylation
• rhodium