Nitropyrroles and nitroindoles: cycloaddition reactions assisted by microwave irradiation: solvent effect. An experimental-theoretical study.

KNEETEMAN, MARÍA N.; MANCINI, PEDRO M. E.; ORMACHEA, CARLA M.

Milán

Workshop; 4th international Workshop on Pericyclic Reactions and Synthesis of Hetero- and Carbocyclic Systems; 2017

Centro Interuniversitario di Ricerca Sulle Reazioni Pericicliche e Sintesi di Sistemi Etero e Carbociclici (CIRP)

Specific polar Diels-Alder (P-DA) reactions using aromatic carbo- and heterocyclic nitro-substituted dienophiles and different dienes were developed in last years. In general, these cited polar cycloaddition are a domino process initialized by a P-DA reaction to give the formally [4+2] cycloadduct followed for the subsequent irreversible elimination of nitrous acid which is the responsible factor for the feasibility of the overall process. Considering the potential influence of the solvents and its specific effect, the reactions were developed under conventional thermal conditions using toluene or protic ionic liquids (PILs) as reaction media. The experimental results showed that using neoteric solvents the reactions were faster that those developed in traditional organic solvent.