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3. Tandem Michael addition/amino-nitrile cyclization from 2-formyl-1,4-DHP in the synthesis of novel dihydroindolizine-based compounds

Author

Marchalin, Stefan, Baumlova, Barbora, Baran, Peter, Oulyadi, Hassan, and Daich, Adam

Subjects
Ring formation (Chemistry) -- Analysis, Indole -- Chemical properties, Nitriles -- Chemical properties, Biological sciences, Chemistry
Abstract

A simple and efficient methodology for the synthesis of a small library of substituted indolizines with different degrees of saturation starting from the racemic 2-formyl-1,4-DHP reagent is presented. The main step of the sequential reaction was based on the highly diastereoselective tandem Michael addition/intramolecular amino-nitrile cyclization catalyzed by an organic base, which produced 1,7-dihydroindolizines in a diastereoselective manner.

Published
2006

4. Pi-aromatic and sulfur nucleophilic partners in cationic pi-cyclizations: intramolecular amidoalkylation and thioamidoalkylation cyclization via omega-carbinol lactams

Author

Hucher, Nicolas, Decroix, Bernard, and Daich, Adam

Subjects
Chemistry, Organic -- Research, Aromatic compounds -- Physiological aspects, Sulfur -- Physiological aspects, Acids -- Physiological aspects, Atoms -- Research, Ions -- Research, Methanol -- Physiological aspects, Biological sciences, Chemistry
Abstract

Research has been conducted on the ring closure reactions. Results indicate that these reactions proceed via a nicleophilic attack of the electron pi-aromatic or the lone sulfur atom pair onto the endo- or exocyclic N-acyliminium ions generated from the omega-carbinol lactams under acidic conditions.

Published
2001

5. New and expeditious tandem sequence aza-Michael/intramolecular nucleophilic substitution route to substituted [gamma]-lactams: synthesis of the tricyclic core of (+-)-martinellines

Author

Comesse, Sebastien, Sanselme, Morgane, and Daich, Adam

Subjects
Nucleophilic reactions -- Analysis, Alkaloids -- Structure, Biological sciences, Chemistry
Abstract

A new and highly diastereoselective tandem reaction aza-Michael/intramolecular nucleophilic substitution and the synthesis of the tricyclic core of (+-)-martinelline alkaloids are described. The unprecedented tandem reaction between N-substituted [alpha]-bromoacetamides and Michael has provided the corresponding trisubstituted [gamma]-lactam systems.

Published
2008

6. A domino N-amidoacylation/aldol-type condensation approach to the synthesis of the topo-I inhibitor rosettacin and derivatives

Author

Pin, Frederic, Comesse, Sebastien, Sanselme, Morgane, and Daich, Adam

Subjects
Acylation -- Analysis, Carboxylation -- Analysis, Heterocyclic compounds -- Chemical properties, Biological sciences, Chemistry
Abstract

A novel domino N-amidoacylation/aldol-type condensation followed by decarboxylation of the ester function was used to perform the pot, atom and step-economic synthesis of rosettacin topo-I poison and its derivatives. The key step in the process involves mixing HOBt ester as new reagent with lactam and NaH together in THF or THF/DMF which yields moderate to good N-heterocyclic products.

Published
2008

7. Intermolecular and intramolecular [alpha]-amidoalkylation reactions using bismuth triflate as the catalyst

Author

Pin, Frederic, Comesse, Sebastien, Garrigues, Bernard, Marchalin, Stefan, and Daich, Adam

Subjects
Bismuth -- Structure, Bismuth -- Chemical properties, Ring formation (Chemistry) -- Analysis, Nuclear magnetic resonance spectroscopy -- Analysis, Biological sciences, Chemistry
Abstract

A catalytic amount of bismuth triflate (Bi[(OTf).sub.3]) was used to study intermolecular [alpha]-amidoalkylation of various [alpha]-acetoxy lactams with C-nucleophiles. The results compared with classical Lewis acids as catalysts showed that the use of bismuth(II) triflate is very efficient for nearly all [alpha]-acetoxy lactams utilized, except for N-acyliminium precursors bearing a sulfur atom.

Published
2007

8. General and versatile entry to 4,5-fused polycyclic imidazolones systems. Use of the tandem transposition/pi-cyclization of N-acyliminium species

Author

Pesquet, Anthony, Daich, Adam, and Van Hijfte, Luc

Subjects
Ring formation (Chemistry) -- Analysis, Ketones -- Structure, Ketones -- Chemical properties, Gel permeation chromatography -- Usage, Biological sciences, Chemistry
Abstract

A description of a simple and efficient four-step methodology for the synthesis of 4,5-fused imidazolidin-2-on3 from bicyclic and tricyclic ketones is provided. The process seems to be easy, general, regiospecific, resulted in the formation of polyheterocyclic systems containing an imidazolidin-2-one nucleus in good to excellent yields, and is compatible with a large-scale production.

Published
2006

9. New resolution of 2-formyl-1,4-DHP derivatives using CIDR methodology. Facile access to new chiral tricyclic thiolactam

Author

Marchalin, Stefan, Cvopova, Katarina, Kriz, Miroslav, Baran, Peter, Oulyadi, Hassan, and Daich, Adam

Subjects
Phenethylamines -- Analysis, Biological sciences, Chemistry
Abstract

(R)- and (S)-Alpha-phenylethylamine (Alpha-PEA: 7) is used seperately to resolve successfully a racemate 2-formyl-1,4-DHP derivative 4. It is recognized that the absolute configuration at the C(sub 4) position of the 1,4-DHP nucleus is indispensable for activity modulation.

Published
2004

10. Benefits of Ryegrass on Multicontaminated Soils Part 2: A Green Process to Provide Idrocilamide

Author

Brice Louvel, Pierrick Dufrénoy, Alina Ghinet, Christophe Waterlot, Adam Daïch, Marie Hechelski, Laboratoire de Génie Civil et Géo-Environnement (LGCgE) - ULR 4515 (LGCgE), Université d'Artois (UA)-Université de Lille-Ecole nationale supérieure Mines-Télécom Lille Douai (IMT Lille Douai), Institut Mines-Télécom [Paris] (IMT)-Institut Mines-Télécom [Paris] (IMT)-JUNIA (JUNIA), Biotechnologie et Gestion des Agents Pathogènes en agriculture (BioGAP), Institut Supérieur d'Agriculture de Lille (ISA)-Institut Charles Viollette (ICV) - ULR 7394 (ICV), Université d'Artois (UA)-Université du Littoral Côte d'Opale (ULCO)-Institut Supérieur d'Agriculture-Université de Lille-Institut National de Recherche pour l’Agriculture, l’Alimentation et l’Environnement (INRAE)-Université d'Artois (UA)-Université du Littoral Côte d'Opale (ULCO)-Institut Supérieur d'Agriculture-Université de Lille-Institut National de Recherche pour l’Agriculture, l’Alimentation et l’Environnement (INRAE), Unité de Recherche en Chimie Organique et Macromoléculaire (URCOM), Université Le Havre Normandie (ULH), Normandie Université (NU)-Normandie Université (NU), Hautes Etudes d’Ingénieur [Lille] (HEI), Lille Inflammation Research International Center - U 995 (LIRIC), Centre Hospitalier Régional Universitaire [Lille] (CHRU Lille)-Institut National de la Santé et de la Recherche Médicale (INSERM)-Université de Lille-Institut Pasteur de Lille, Réseau International des Instituts Pasteur (RIIP)-Réseau International des Instituts Pasteur (RIIP), Institut Normand de Chimie Moléculaire Médicinale et Macromoléculaire (INC3M), Institut de Chimie du CNRS (INC)-École Nationale Supérieure d'Ingénieurs de Caen (ENSICAEN), Normandie Université (NU)-Normandie Université (NU)-Institut national des sciences appliquées Rouen Normandie (INSA Rouen Normandie), Institut National des Sciences Appliquées (INSA)-Normandie Université (NU)-Institut National des Sciences Appliquées (INSA)-Université Le Havre Normandie (ULH), Normandie Université (NU)-Université de Rouen Normandie (UNIROUEN), Normandie Université (NU)-Centre National de la Recherche Scientifique (CNRS)-Université de Caen Normandie (UNICAEN), Normandie Université (NU), Alexandru Ioan Cuza University of Iași [Romania], The authors warmly thank the 'Fondation de la Catho de Lille, France' and Yncréa Hauts-de-France for the financial support of this work., DAICH, ADAM, Université catholique de Lille (UCL)-Université catholique de Lille (UCL), Institut Charles Viollette (ICV) - ULR 7394 (ICV), JUNIA (JUNIA), Institut Pasteur de Lille, Réseau International des Instituts Pasteur (RIIP)-Réseau International des Instituts Pasteur (RIIP)-Institut National de la Santé et de la Recherche Médicale (INSERM)-Université de Lille-Centre Hospitalier Régional Universitaire [Lille] (CHRU Lille), Université de Caen Normandie (UNICAEN), Normandie Université (NU)-Normandie Université (NU)-École Nationale Supérieure d'Ingénieurs de Caen (ENSICAEN), Normandie Université (NU)-Université Le Havre Normandie (ULH), Normandie Université (NU)-Institut national des sciences appliquées Rouen Normandie (INSA Rouen Normandie), and Institut National des Sciences Appliquées (INSA)-Normandie Université (NU)-Institut National des Sciences Appliquées (INSA)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)

Subjects
Green chemistry, biosourced catalyst, ryegrass, synthesis, [CHIM.THER] Chemical Sciences/Medicinal Chemistry, Geography, Planning and Development, [CHIM.THER]Chemical Sciences/Medicinal Chemistry, 010501 environmental sciences, Management, Monitoring, Policy and Law, 010402 general chemistry, 01 natural sciences, law.invention, Catalysis, metrics, chemistry.chemical_compound, law, Calcination, 0105 earth and related environmental sciences, Renewable Energy, Sustainability and the Environment, Chemistry, green chemistry, [CHIM.ORGA]Chemical Sciences/Organic chemistry, [CHIM.CATA] Chemical Sciences/Catalysis, [CHIM.CATA]Chemical Sciences/Catalysis, Contamination, [CHIM.ORGA] Chemical Sciences/Organic chemistry, 6. Clean water, 0104 chemical sciences, Environmental chemistry, Yield (chemistry), Shoot, Soil water, Idrocilamide
Abstract

A restoration of highly contaminated garden soil is proposed as a greener alternative to the production of vegetables. Depending on potentially toxic elements and their concentration, ryegrass shoots accumulate these elements in sufficient quantity to be used as a catalyst in organic synthesis. The analysis of Cd, Pb, Zn, Cu, Fe, Mn, and Al in ashes issued from the calcination of ryegrass shoots revealed that the concentration of Zn was highest (&gt, 7000 mg kg&ndash, 1). The ratios between potential Lewis acids (Zn, Cu, Fe, Mn, and Al) to carcinogenic metals (Cd or Pb) were 191 &plusmn, 7 for LA/Cd and 235 &plusmn, 13 for LA/Pb, making the shoots of ryegrass suitable for the production of Zn-rich polymetallic biosourced catalysts. This material was used in the synthesis of idrocilamide under free-solvent condition, providing the drug in a good yield (69.9%). Data show that a limitation of waste, a maximization of the material incorporation in the process, a minimization of the steps, and an optimization of the stoichiometric factor are the main innovative factors in the current process in comparison with those previously reported.

Published
2019

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