The Groebke-Blackburn-Bienaymé reaction in its maturity: innovation and improvements since its 21st birthday (2019-2023).

The Groebke-Blackburn-Bienaymé (GBB) three-component reaction, discovered in 1998, is a very efficient strategy to assemble imidazo[1,2-]-heterocycles starting from amidines, aldehydes and isocyanides. This review aims to exhaustively describe innovative aspects of this reaction achieved during the last five years, and classifies them into five categories: synthetic methods, building blocks, scaffolds, biological activities and physical properties.

Ultrasound-assisted-one-pot synthesis and antiplasmodium evaluation of 3-substituted-isoindolin-1-ones.

As the attempts to control malaria through chemotherapy strategies are restricted, we have prepared a small library of 3-substituted-isoindolinones from ()-3-benzylideneisobenzofuran-1(3)-ones in one-pot fashion under ultrasound irradiation. The one-pot reaction was scalable and efficiently produced the desired products (1a-m) in high yields in a short reaction time. Evaluation of their antiplasmodium assay against the 3D7 (chloroquine-sensitive) and FCR3 (chloroquine-resistant) strains of demonstrated that they displayed moderate to strong antiplasmodium activities (the IC values ranging from 4.

Ultrasonic-assisted-synthesis of isoindolin-1-one derivatives.

A small library of 3-hydroxyisoindolin-1-ones has been prepared from 3-alkylidenephtalides under ultrasonic irradiation. This practical synthesis is featured by group tolerance, high efficiency and yields. The reaction can also be performed in multigram scale and be further extended to access other motifs of isoindolin-1-ones in a one-pot fashion.

Enantioselective Construction of Tetrasubstituted Carbon Stereocenters via Chiral Phosphoric Acid-Catalyzed Friedel-Craft Alkylation of Indoles with 5-Substituted Hydroxybutyrolactams.

The first intermolecular organocatalytic enantioselective addition of indoles to prochiral 5-membered cyclic -acyliminium ions, generated from 5-hydroxy-α,β-unsaturated pyrrolidin-2-ones, is reported hereinafter. The reaction proceeds smoothly with a range of 5-hydroxy-5-substituted-α,β-unsaturated pyrrolidin-2-ones and indoles using BINOL-derived phosphoric acid catalyst to afford α,β-unsaturated lactams embedding a tetrasubstituted stereogenic center in high yields and enantioselectivities.

[Not Available].

The therapy for invasive candidiasis related to biofilms infection remains a difficult medical problem. To overcome this problem, efforts have been made to search for novel antibiofilm agents from various sources. This study investigated the in vitro antibiofilm activity of (1)-N-2-methoxybenzyl-1,10-phenanthrolinium bromide (FEN) against Candida albicans.