Intramolecular amidoalkylation of aromatics. II. Synthesis of conformationally restriced bridged peptides analogues of Phg-Gly or Gly-Phg

Article abstract of DOI:10.1016/S0040-4020(01)80154-X

Derivatives of Phg-α-MeO-GlyOH(3) and its isomer α-MeO-Gly-Phg(2) were prepared and their inter and intramolecular amidoalkylation reactions were studied. Derivatives of 2 underwent smooth cyclization to give 4-amino-3-isoquinolon-1-carboxylic acid derivatives (4, 8). The isomer 3, which reacted smoothly intermolecularly with toluene to give the open chain peptide 7, reacted sluggishly intramolecularly.