SYNTHESIS AND SPECTROSCOPIC PROPERTIES OF 1,6-METHANO-[10]ANNULENE-FUSED AND 2,4-DIMETHYL-7,12-METHANO-3H-CYCLOHEPTA[10]ANNULEN-3-ONE-FUSED 10H-PYRROLO[1,2-a]- PERIMIDIN-10-ONES

摘要

The title 1,6-methano[10]annulene-fused and 2,4-dimethyl-7,12-methano-3H-cyclohepta[10]annulen-3-one-fused 10H-pyrrolo[1,2-a]perimidin-10-ones, denoted by 2 and 3, respectively, were synthesized. A novel and efficient synthetic method involving tandem [4 + 3] cycloaddition and 10π -electrocyclization was developed for constructing the 2,4-dimethyl-7,12-methano-3H-cyclohepta[10]annulen-3-one skeleton toward the synthesis of 3 from 6H-cyclohepta[c]furan-5,7-dicarbaldehyde (5). Spectroscopic properties of 2 and 3 were also described in relation to the tropone-fusion.