α-Halogenoacetamides: versatile and efficient tools for the synthesis of complex aza-heterocycles

International audienceThis review provides an overview of the applications of α-halogenoacetamides in domino and cycloaddition reactions. α-Halogenoacetamides are versatile building blocks that can lead to a wide variety of complex aza-heterocycles of biological interest when engaged in domino and/or cycloaddition reactions. The reactivity and the reaction conditions involved for these species (solvent, base, etc.) are closely related to the substituent onto the nitrogen atom of the amide: N-alkyl α-halogenoacetamides usually act as formal 1,3-dipoles in domino processes whereas N-alkoxy derivatives often react as real 1,3-dipoles via the formation of aza-oxyallyl cation species. This important modulation of the reactivity of these compounds opens the way to a large panel of reactions and therefore to a large diversity of aza-heterocycles

2,3‐Epoxyamide‐alcohols in Domino Reactions: En Route to Molecular Diversity

International audienceThe synthesis of polycyclic γ‐ and δ‐lactams bearing up to four contiguous fully controlled stereocenters is presented. For that purpose, we developed an original approach based on the use of 2,3‐epoxyamides in domino reactions by taking advantage of the nucleophilic nitrogen atom and electrophilic epoxide. In reaction with enol ethers bearing gem bis‐electrophiles on the double bond as Michael acceptors, four different reaction pathways were observed. They all started with a domino oxa‐Michael/aza‐Michael/epoxide opening sequence and depending on substrates engaged could be followed either by a lactonization or a hemiketalization/retro‐aldol cascade. Thus, four original fully‐substituted piperidine‐ or pyrrolidine‐2‐one scaffolds were selectively synthesized in good to high yields. Moreover, these polycyclic lactams were obtained in high stereo‐ and chemo‐selectively highlighting the efficiency and molecular diversity offered by this new methodology that should offer various synthetic opportunities in the future

Synthèse de nouveaux dérivés du 9-hydroxy-parthénolide contenant un noyau -1,2,3-triazole substitué

National audienc

Suzuki–Miyaura Reactions of Halospirooxindole Derivatives.

International audienceStarting from 5,5′-dihalo-1′-pentyl-2H-spiro[furo[2,3-b]pyridine-3,3′-indolin]-2′-one, various 5,5′-di(het)aryl-1′-pentyl-2H-spiro[furo[2,3-b]pyridine-3,3′-indolin]-2′-ones were synthesized through palladium-catalysed cross-coupling reactions. A large panel of boronic acids (aryl or heteroaryl) could easily be introduced, leading to a library of new 5- or 5′-monosubstituted and 5,5′-disubstituted 1′-pentyl-2H-spiro[furo[2,3-b]pyridine-3,3′-indolin]-2′-ones

Synthesis of Oxazolidin-4-ones: Domino O -Alkylation/Aza-Michael/Intramolecular Retro-Claisen Condensation

International audienc

A general and efficient method to access tetracyclic spirooxindole derivatives.

International audienceAn efficient, simple, and convenient synthetic procedure for the synthesis of tetracyclic spirooxindole derivatives, starting from N-protected isatins and 2-fluoropyridine, was successfully developed. It enables the facile formation of a new class of spirooxindoles in which the oxindole core is fused with various heterocycles at the C-3 position

Chemo-, Regio-, and Stereoselective Synthesis of Polysusbtituted Oxazolo[3,2- d ][1,4]oxazepin-5(3 H )ones via a Domino oxa-Michael/aza-Michael/Williamson Cycloetherification Sequence

International audienc

Synthesis and anticancer evaluation of novel 9 alpha-substituted-13-(1,2,3-triazolo)-parthenolides

A series of novel 9 alpha-substituted-13-(1,2,3-triazolo)-parthenolides 3-20 were efficiently synthesized and tested for their in vitro anticancer activity using the MTT colorimetric assay against four human cancer cell lines. 9 alpha-Substituted-13-(1,2,3-triazolo)-parthenolide derivatives were prepared by the diastereoselective Michael addition of TMSN3 onto 9 alpha-hydroxyparthenolide 1 to give the key intermediate 9 alpha-trimethylsilyloxy-13-(1,2,3-triazolo)-parthenolide 2 which was utilized in a regioselective Huisgen 1,3-dipolar cycloaddition reaction with various alkynes to afford 1,4-disubstituted-1,2,3-triazoles of 9 alpha-substituted-parthenolide. (C) 2016 Elsevier Ltd. All rights reserved

Pyrrolo-imidazo[1,2- a ]pyridine Scaffolds through a Sequential Coupling of N -Tosylhydrazones with Imidazopyridines and Reductive Cadogan Annulation, Synthetic Scope, and Application

International audienc

Gold catalysis: A one-pot intermolecular Fridel-Crafts type α-amidoalkylation/hydroarylation sequences by N-acyliminium ion chemistry

International audienc