In this thesis some diols 6b,11b-dihydroxy-12-(alkyl/aryl)-12b,11-dihydrobenzo[g]indeno[1,2-b]indole-5,6,7(6bH)-trione were prepared from the reaction of ninhydrin and aminonaphtoquinones. Then room temperature oxidative cleavage of these compounds using periodic acid in acetic acid was resulted to efficient preparation of piro[benzo[g]indole-2,1'-isobenzofuran]-3,3',4,5(1H)- 1tetraones. In the following the resulted spiro[benzo[g]indolobenzofurans) were reacted with various alkyl/aryl-1,2-diamines in acetic acid for efficient preparation of spiro[benzo/dibenzo[a,i]pyrrolo[2,3-c]phenazine-2,1'-isobenzofuran]-1,3'(3H)-dione and spiro[benzo[f]pyrrolo[2,3-h]quinoxaline-2,1'-isobenzofuran]-3,3'(1H)-diones. Additionally 8-(alkyl/aryl)-10,11-dihydro-7H-benzo[b]naphtho[1,8-ef]azocinetriaone were prepared from the one-pot reaction of acenaphthenequinoe with various cyclic and acyclic enaminons followed by room temperature oxidation of the resulted diols with periodic acid.
In continiouse, oxidation of diols resulted from the reaction of β-diketone and acenaphthenequinoe using periodic acid caused to preparation of alkyl 8-heteroarylcarbonyl-1-naphthat in good to excellent yields.
In the last part of this thesis at first some diols 8b,13b-dihydroxy8b,9,10,13b-tetrahydro-11H-dibenzo[e,g]pyrimido[4,5-b]indole-11,13(12H)-dione were synthesized from the reaction phenanthrene-9,10-dione and aminouracil derivatives using AcOH as solvent under reflux conditions. Then 11(alkyl)-9Hdibenzo[e,g]pyrimido[4,5-b]azonine-9,12,14,15(10H,11H,13H)-tetraone drivatives were synthesized via the periodic acid-mediated oxidative cleavage of vicinal cyclic diols in acetic acid at at 70oC in good yields.