Convenient construction of spiro[indoline-3,5’-pyrrolo[3,4-c] carbazole] and spiro[indene-2,5’-pyrro

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p-TsOH catalyzed Diels-Alder reaction of 3-(indol-3-yl)maleimides with 3-phenacylideneoxindoles in toluene at 80 C for two hours afforded cis/trans isomers of 3a’,4 ,6 ,10c’-tetrahydrospiro[indoline-3,5-pyrrolo[3,4-c]carbazoles] in nearly comparable yields, which could be easily converted to the corresponding 4 ,6-dihydrospiro[indoline-3,5-pyrrolo[3,4-c]carbazole] in high yields and with high diastereoselectivity by further DDQ oxidation. Additionally, the similar reaction of 3-(indol-3-yl) maleimides with 2-arylidene-1,3-indanediones in toluene 80 C and sequential DDQ oxidation afforded functionalized dihydrospiro[indene-2,5-pyrrolo[3,4-c]carbazoles] as major products.
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