Synthesis of 4-Hydroxycarbazole Derivatives by Benzannulation of 3-Nitroindoles with Alkylidene Azlactones.

A general synthesis of 4-hydroxylcarbazoles by domino vinylogous conjugate addition/cyclization/elimination/aromatization of easily prepared 3-nitroindoles with alkylidene azlactones under mild and transition-metal-free conditions has been developed. This method was also applicable to other nitrosubstituted benzofused heterocycles such as 3-nitrobenzothiophene, 2-nitrobenzothiophene, and 2-nitrobenzofuran. The valuable tetracyclic carbazole derivatives, such as 6H-oxazolo[4,5-c]carbazole and 3,6-dihydro-2H-oxazolo[4,5-c]carbazol-2-one, were readily prepared from the product, demonstrating synthetic utility of this method.