Dinucleophilic Reactivity of Isocyanoacetate: Base-Catalyzed One-Pot Access to 4-Azafluorenes and 4-Azafluorenones

A base-catalyzed double annulation of isocyanoacetates with various enynones has been developed for the expeditious synthesis of 4-azafluorene and 4-azafluorenone derivatives. Against the well-known 1,3-dipolar reactivities, the active methylene and isocyano groups of isocyanoacetate serve as nucleophiles in this domino transformation.

Automated summary

A base-catalyzed double annulation methodology has been developed for the efficient synthesis of 4-azafluorene and 4-azafluorenone derivatives. In contrast to traditional 1,3-dipolar reactions, the active methylene and isocyano groups of isocyanoacetate function as nucleophiles in this domino transformation.