Singlet oxygen-mediated transformation of furans into aromatic nitrogen-containing polycycles in water

Abstract

Dedicated to Professor MichaelAbstract Using a sustainable, green and one-pot protocol, simple furans are transformed into complex aromatic nitrogen-bearing polycycles that are synthetically important. The reaction, which is performed in water, begins with the highly selective and mild photooxidation of the furan substrate with singlet oxygen.

Chemoselective photooxygenations of furans bearing unprotected amines: their use in alkaloid synthesis

“…The common intermediate in all these tandem transformations was a 2-pyrrolidinone. [13][14][15][16][17][18][19] In addition, alternative strategies were pursued by other groups; such as, the incorporation into the furan photooxygenation substrates of nitrogen motifs such as azide groups, 20 or Boc-protected amine groups. 20,21 The inclusion of free and nucleophilic nitrogen functionalities within furan photooxygenation substrates, however, remained notably absent and could have been described as seriously curtailing the synthetic utility of such chemistry.…”