One-Pot Heteroarene Synthesis Based on Ruthenium-on-Carbon-Catalyzed Oxidative Aromatization Using Oxygen

Various heteroarenes, such as indole, carbazole, dibenzofuran, dibenzothiophene, etc., were easily constructed by the Diels-Alder reaction of the corresponding vinyl-substituted pyrrole, indole, benzofuran or benzothiophene with the dienophiles and the subsequent heterogeneously ruthenium-on-carbon (Ru/C)-catalyzed oxidative aromatization using oxygen in a one-pot manner. Furthermore, the one-pot synthesis of the tetrahydropyrrolo[3,4-a]carbazole-1,3-dione derivative possessing the critical backbone of the antitumor agent was also accomplished by the following construction of the phthalimide moiety. The one-pot synthesis of indole as well as carbazole, dibenzofuran and dibenzothiophene derivatives based on the Diels-Alder reaction between the corresponding vinyl-substituted heteroarenes and dienophiles and subsequent ruthenium-on-carbon (Ru/C)-catalyzed aromatization reaction was developed. Furthermore, the construction of tetrahydropyrrolo[3,4-a]carbazole-1,3-dione derivatives were also accomplished in a one-pot manner.