Useful procedures for fluorocyclization of tryptamine and tryptophol derivatives to 3a-fluoropyrrolo[2,3-b]indoles and 3a-fluorofuro[2,3-b]indoles

•Versatile procedures for fluorocyclization of tryptamine and tryptophol derivatives were developed.•Various kinds of 3a-fluoropyrrolo(furo)[2.3-b]indoles were obtained successfully according to our procedures.•N-fluoro-2,4,6-trimethylpyridinium triflate (FP-T300) or Selectfluor™ is effective for fluorocyclization.•Electron-withdrawing groups at the indole nitrogen or 5-position lowers reactivity of fluorocyclization.•Use of NaHCO3 as an acid trap can improve the yields of acid-labile 3a-fluoropyrrolo(furo)[2.3-b]indoles.

Versatile procedures for fluorocyclization of various tryptamine and tryptophol derivatives to obtain the corresponding 3a-fluoropyrrolo[2.3-b]indoles and 3a-fluorofuro[2.3-b]indoles, respectively were developed employing N-fluoro-2,4,6-trimethylpyridinium triflate (FP-T300) or Selectfluor™ as the electrophilic fluorinating agent. The use of NaHCO3 for fluorocyclization was effective in improving the yield of acid-labile fluoropyrrolo(furo)indoles. Our procedures are especially useful for the synthesis of fluoropyrrolo(furo)indoles bearing a free NH indole group.

Graphical abstractVersatile procedures for fluorocyclization of various kinds of tryptamine and tryptophol derivatives to obtain the corresponding 3a-fluoropyrrolo(furo)[2.3-b]indoles were developed.Figure optionsDownload full-size imageDownload as PowerPoint slide