Concise and Free-Metal Access to Lactone-Annelated Pyrrolo[2,1-<i>a</i>]isoquinoline Derivatives via a 1,2-Rearrangement Step

Abstract

Here, An efficient approach to obtaining previously unknown furo[2′,3′:2,3]pyrrolo[2,1-a]isoquinoline derivatives from readily available 1-R-1-ethynyl-2-vinylisoquinolines is described. The reaction features a simple procedure, occurs in hexaflouroisopropanol and does not require elevated temperatures. It has been found that the addition of glacial acetic acid significantly increases the yields of the target spirolactone products. Using trifluoroethanol instead of hexaflouroisopropanol results in the formation of pyrido[2,1-a]isoquinolines.

Keywords

• hexaflouroisopropanol
• lactonic pyrrolo[2,1-<i>a</i>]isoquinolines
• pyrido[2,1-<i>a</i>]isoquinolines
• [1,2]-sigmatropic rearrangement
• trifluoroethanol