Natural deep eutectic solvents in the hetero-Diels-Alder approach to bis(indolyl)methanes

Grosso, Carla; Brigas, Amadeu; de los Santos, Jesus M.; Palacios, Francisco; Lemos, Americo; Pinho e Melo, Teresa M. V. D.

http://hdl.handle.net/10400.1/14304

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Authors

Grosso, Carla

Brigas, Amadeu

de los Santos, Jesus M.

Palacios, Francisco

Lemos, Americo

Pinho e Melo, Teresa M. V. D.

Abstract(s)

For the first time, the use of natural deep eutectic solvents (NADES) as reaction media to carry out hetero-Diels-Alder reactions is disclosed. This allowed to improve the efficiency and sustainability of the synthetic approach to bis(indolyl)methanes (BIMs) based on bis-hetero-Diels-Alder/conjugate addition reactions of nitroso- and azoalkenes with indoles. The ternary mixture of H2O with choline chloride/glycerol allowed the tuning of the physical properties of this NADES leading to a better solvent system, affording the target hydroxyiminomethyl- and hydrazonomethyl-BIMs, in much shorter reaction times, higher efficiency and easier isolation procedures. Furthermore, the direct access to carbonyl-BIMs was possible when 3-methyl-1-tert-butoxycarbonyl azoalkenes were used. [GRAPHICS] .

Keywords

Active pharmaceutical ingredients Catalytic asymmetric-synthesis Carbonyl-compounds Vibrio-parahaemolyticus Indole alkaloids Ionic liquids Oximes Nitrosoalkenes Deoximation Mild