NOVEL EFFICIENT SYNTHESIS AND PROPERTIES OF 5,6-DIHYDROCYCLOHEPTA[b]INDOL-6-ONE, AND ITS TRANSFORMATION TO 6-AZOLYL-5-AZABENZ[b]AZULENES

摘要

The title compound, 5,6-dihydrocyclohepta[b]indol-6-one (1), was synthesized from 2-chlorotropone (7) by a two-step sequence involving Pd-catalyzed amination with 2-bromoaniline (15) and subsequent Pd-catalyzed intramolecular Heck reaction. Besides its synthetic detail, some physical properties of 1, such as acidity, basicity and spectroscopic behavior, were also reported. Compound 1 was transformed into 6-(1H-pyrazol-1-yl)-and 6-(1H-1,2,3-triazol-1-yl)-5-azabenz[b]azulenes (13 and 14) as a potential ligand.