Synthesis of Functionalized 3<i>H</i>-pyrrolo-[1,2,3-<i>de</i>] Quinoxalines via Gold-Catalyzed Intramolecular Hydroamination of Alkynes
Antonia Iazzetti,
Giancarlo Fabrizi,
Antonella Goggiamani,
Federico Marrone,
Alessio Sferrazza,
Karim Ullah
Affiliations
Antonia Iazzetti
Dipartimento di Scienze Biotecnologiche di Base, Cliniche Intensivologiche e Perioperatorie, Università Cattolica del Sacro Cuore, L.go Francesco Vito 1, 00168 Rome, Italy
Giancarlo Fabrizi
Dipartimento di Chimica e Tecnologie del Farmaco, Sapienza, Università di Roma, P. le A. Moro 5, 00185 Rome, Italy
Antonella Goggiamani
Dipartimento di Chimica e Tecnologie del Farmaco, Sapienza, Università di Roma, P. le A. Moro 5, 00185 Rome, Italy
Federico Marrone
Dipartimento di Chimica e Tecnologie del Farmaco, Sapienza, Università di Roma, P. le A. Moro 5, 00185 Rome, Italy
Alessio Sferrazza
Dipartimento di Chimica e Tecnologie del Farmaco, Sapienza, Università di Roma, P. le A. Moro 5, 00185 Rome, Italy
Karim Ullah
Dipartimento di Chimica e Tecnologie del Farmaco, Sapienza, Università di Roma, P. le A. Moro 5, 00185 Rome, Italy
A gold-catalyzed protocol to obtain functionalized 3H-pyrrolo [1,2,3-de] quinoxalines from suitable substituted N-alkynyl indoles has been proposed. The mild reaction conditions were revealed to be compatible with different functional groups, including halogen, alkoxyl, cyano, ketone, and ester, allowing the isolation of title compounds with yields from good to high. A reaction mechanism has been proposed, and theoretical calculations have been provided to rationalize the final step of the hypothesized reaction mechanism. As quinoxaline-containing polycyclic compounds, this class of molecules may represent a valuable template in medicinal chemistry and material science.
