Hetero-Diels-Alder approach to Bis(indolyl)methanes

Grosso, Carla; Cardoso, Ana L.; Rodrigues, Maria Joao; Marques, Catia; Barreira, Luísa; Lemos, Americo; Pinho e Melo, Teresa M. D. V.

http://hdl.handle.net/10400.1/13234

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Authors

Grosso, Carla

Cardoso, Ana L.

Rodrigues, Maria Joao

Marques, Catia

Barreira, Luísa

Lemos, Americo

Pinho e Melo, Teresa M. D. V.

Abstract(s)

A novel synthetic approach to bis(indolyl)methanes has been established. Our one-pot synthetic strategy based on two consecutive hetero-Diels-Alder cycloaddition reactions of electrophilic conjugated nitrosoalkenes with indoles was extended to a range of new 1-hydroxyiminomethyl-bis(indolyl) methanes. Furthermore, a similar and broad range approach was applied to the synthesis of previously unknown 1-hydrazonomethyl-bis(indolyl)methanes. The biological evaluation of the new bis(indolyl) methanes as anti-cancer agents was investigated. (C) 2016 Elsevier Ltd. All rights reserved.

Keywords

Friedel-crafts reactions Enantioselective synthesis Bis-indolylmethanes Recyclable catalyst Carbonyl-compounds Terminal alkynes Indoles Derivatives Nitrosoalkenes Activation