1. Natural deep eutectic solvents in the hetero-Diels–Alder approach to bis(indolyl)methanes.
- Author
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Grosso, Carla, Brigas, Amadeu, de los Santos, Jesús M., Palacios, Francisco, Lemos, Américo, and Pinho e Melo, Teresa M. V. D.
- Abstract
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 H
2 O 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. [ABSTRACT FROM AUTHOR]- Published
- 2019
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