Domino reaction of bindone and 1,3-dipolarophiles for the synthesis of diverse spiro and fused indeno[1,2-]fluorene-7,12-diones.

The base promoted domino reaction of bindone ([1,2'-biindenylidene]-1',3,3'-trione) with common 1,3-dipolarophiles showed interesting molecular diversities, from which the unique spiro and fused indeno[1,2-]fluorine derivatives were conveniently synthesized in satisfactory yields. In the presence of a base, bindone underwent formal [3 + 3] cycloaddition with satylidene malononitriles to give dispiro[indene-2,4'-fluorene-1',3''-indoline]. It also underwent formal [4 + 2] cycloaddition with 4-arylidene-pyrazol-3-ones to give diastereoisomeric spiro[indeno[1,2-]fluorene-5,4'-pyrazole]. On the other hand, a triethylamine promoted reaction of three molecules of 1,3-indanediones and isatins in toluene afforded spiro[diindeno[2,1-:2',1'-]anthracene-11,3'-indoline] derivatives through the domino [4 + 2] cycloaddition and ring-expansion process.