Search results for "synthetic method"
showing 10 items of 15 documents
Acid-induced rearrangement of epoxygermacra-8,12-olides: synthesis and absolute configuration of guaiane and eudesmane derivatives from artemisiifolin
2010
A study on the acid-induced rearrangement of 4,5-epoxy- and 1,10-epoxygermacra-8,12-olides was carried out. From a 4,5-epoxy derivative, guaianes were obtained, whereas 1,10-epoxy derivatives furnished, depending on the stereochemistry of the C-1/C-10 epoxy ring, trans-5β,10α- or trans-5α,10β-eudesmanolides.
Synthesis of Isoxazoline Derivatives through Boulton–Katritzky Rearrangement of 1,2,4-Oxadiazoles
2013
The base-induced rearrangement of 1,2,4-oxadiazoles into isoxazoline derivatives is reported. This represents the first example of a three-atom side-chain rearrangement that involves a saturated CCO side chain at C-3 of the oxadiazole. Nonaromatic 3-amino-isoxazoline derivatives are obtained in good yields. Interestingly, this reaction occurs through the rearrangement of aromatic oxadiazoles to form less stable bonds than those that are broken.
Thiazolium-based catalysts for the etherification reaction of benzylic alcohols under solvent-free condition
2015
Thiazolium and imidazolium hybrid materials were prepared by radical reactions between a mercaptopropyl-modified SBA-15 mesoporous silica and bis-vinylthiazolium or bis-vinylimidazolium dibromide salts. These hybrid materials were characterized by several techniques and were employed in the etherification reaction of 1-phenylethanol. Solvent-free conditions at 160C under different gas phases (oxygen, air, nitrogen and argon) were used. The thiazolium-based material displayed excellent performances. Further studies were carried out using unsupported thiazolium salts, with or without a methyl group at the C-2 position of the thiazolium moiety. These studies allowed us to propose a reaction me…
Improved Preparations of Molybdenum Coordination Compounds from Tetrachlorobis(diethyl ether)molybdenum(IV)
2001
International audience; The reduction of MoCl5 with metallic tin in diethyl ether provides a rapid and convenient entry to [MoCl4(OEt2)2] This compound can be transformed easily and in high yields into a variety of other useful synthons. The loss of ether in the solid state affords a new and reactive form of MoCl4. Treatment with THF, PMe3 or LiOtBu affords [MoCl4(THF)2], [MoCl4(PMe3)3] or [Mo(OtBu)4] in high isolated yields. Treatment with metallic tin in THF affords [MoCl3(THF)3] All of these reactions can be carried out under simple experimental conditions and represent significant improvements relative to previously reported syntheses of the same compounds.
Metal‐Free Twofold Electrochemical C−H Amination of Activated Arenes: Application to Medicinally Relevant Precursor Synthesis
2020
Abstract The efficient production of many medicinally or synthetically important starting materials suffers from wasteful or toxic precursors for the synthesis. In particular, the aromatic non‐protected primary amine function represents a versatile synthetic precursor, but its synthesis typically requires toxic oxidizing agents and transition metal catalysts. The twofold electrochemical amination of activated benzene derivatives via Zincke intermediates provides an alternative sustainable strategy for the formation of new C−N bonds of high synthetic value. As a proof of concept, we use our approach to generate a benzoxazinone scaffold that gained attention as a starting structure against ca…
Les exercices gradués dans la méthode du Grammalessico francese a uso degl’italiani d’Arminio Wurmbrand Bianchi
2020
L’article se propose d’analyser les exercices du manuel d’Arminio Wurmbrand Bianchi, Grammalessico francese a uso degl’italiani, qui ont une forme et une structure que l’on retrouve dans de nombreux manuels s’inspirant des méthodes dites « synthétiques ». Wurmbrand, en effet, introduit dans son manuel une nouveauté pour pourvoir au caractère incomplet de la méthode synthétique : il propose, ainsi, avant chaque exercice, la traduction des seuls termes « radicalement dissemblables » des deux langues « similaires à l’origine » qui caractérisent la langue française et la langue italienne. Le but est de fournir aux élèves la maîtrise lexicale de la langue française avec une attention toute parti…
Enantioselective Palladium-Catalyzed Oxidative β,β-Fluoroarylation of α,β-Unsaturated Carbonyl Derivatives
2016
© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim The site-selective palladium-catalyzed three-component coupling of deactivated alkenes, arylboronic acids, and N-fluorobenzenesulfonimide is disclosed herein. The developed methodology establishes a general, modular, and step-economical approach to the stereoselective β-fluorination of α,β-unsaturated systems.
A Versatile Palladium/Triphosphane System for Direct Arylation of Heteroarenes with Chloroarenes at Low Catalyst Loading
2010
International audience; Put a ring on it: The use of an air-stable, robust palladium/tridentate phosphane catalyst in direct C[BOND]H and C[BOND]Cl activation reactions is reported (see scheme; DMAc=N,N-dimethylacetamide, TBAB=tetra-n-butylammonium bromide). Electron-rich, electron-poor, and polysubstituted furans (X=O), thiophenes (X=S), pyrroles (X=NR5), and thiazoles were arylated with chloroarenes in the presence of the catalyst.
Recent Advances on the Halo- and Cyano-Trifluoromethylation of Alkenes and Alkynes
2021
Incorporation of fluorine into organic molecules is a well-established strategy in the design of advanced materials, agrochemicals, and pharmaceuticals. Among numerous modern synthetic approaches, functionalization of unsaturated bonds with simultaneous addition of trifluoromethyl group along with other substituents is currently one of the most attractive methods undergoing wide-ranging development. In this review article, we discuss the most significant contributions made in this area during the last decade (2012−2021). The reactions reviewed in this work include chloro-, bromo-, iodo-, fluoro- and cyano-trifluoromethylation of alkenes and alkynes.
Combining organocatalysis and lanthanide catalysis: a sequential one-pot quadruple reaction sequence/hetero-Diels-Alder asymmetric synthesis of funct…
2016
A stereoselective one-pot synthesis of functionalized complex tricyclic polyethers has been achieved using the combination of secondary amine and lanthanide catalysis. This one-pot quadruple reaction/Hetero-Diels–Alder sequence gave good yields (per step) as well as excellent diastereo- and enantioselectivities. Furthermore, the particular combination of lanthanide complexes with organocatalysis is one of the first examples described for sequential catalysis.