Diastereoselective synthesis of spiro[carbazole-3,5'-pyrimidines] and spiro[carbazole-3,1'-cyclohexanes] via four-component reaction

Functionalized spiro[carbazole-3,5'-pyrimidines] and spiro[carbazole-3,1'-cyclohexanes] were efficiently synthesized in satisfactory yields with high diastereoselectivity by CuSO4 catalyzed multicomponent reaction of indole-2-acetate, aromatic aldehyde and 1,3-dimethylbarbituric acid or dimedone. The reaction was finished with sequential Diels-Alder reaction of both in situ generated indole-2,3-quinodimethane and a dienophile. Additionally, the initially formed spiro[carbazole-3,5'-pyrimidines] were converted to dehydrogenated spiro[carbazole-3,5'-pyrimidines] by DDQ oxidation. The initially formed spiro[carbazole-3,1'-cyclohexanes] were converted to δ-valerolactone-substituted carbazoles by a DDQ promoted Baeyer-Villiger oxidation process.