CONVERSION OF INDOLES INTO QUINOLINES THROUGH THE N-1-C-2 FISSION BY SINGLET-OXYGEN AS A MODEL EXPERIMENT OF BIOMIMETIC SYNTHESIS OF QUININE ALKALOIDS
Photo-oxygenation of indole-3-acetaldehydes (28-30) followed by treatments with dimethyl sulphide and then dilute acetic acid gave 4-acylquinolines (13, 31 and 32), respectively.
PHOTO-OXYGENATION OF INDOLE-3-ACETIC ACIDS AND INDOLE-3-ACETALDEHYDES: BIOMIMETIC CONVERSION OF INDOLES INTO QUINOLINES VIA N1-C2 FISSION
New conversion of indoles to quinolines via the N1-C2 fission using singlet oxygen reaction was investigated starting from indole-3-acetic acids and indole-3-acetaldehydes.Dye-induced photo-oxydation of indole-3-acetaldehyde derivatives (17 and 18) followed by treatments with dimethyl sulfide and then acetic acid produced 4-formyl- and 4-acetylquinolines (19 and 20), respectively.