In this thesis some cyclic vicinal dioles were prepared from the reaction of ninhydrin with phenol derivatives. In continue, their corresponding spiro benzofuran-isobenzofuran derivatives were synthesized in very good yields by oxidative cleavage of diols with periodic acid or lead (IV) acetate at room temperature (schem 1).
In the second part of this thesis, some new 4b,11b-dihydroxy-5,11b-dihydrobenzo[f]indeno[1,2-b]indole-6,11,12(4bH)-trione derivatives were synthesized using one-pot two-step reaction of 1,4-naphtoquinone, aromatic amins and ninhydrin. Then oxidative cleavage of these compounds using periodic acid in acetic acid medium was caused to preparation of spiro[benzo[f]indole-2,1'-isobenzofuran]-3,3',4,9(1H)-tetraones (schem 2).