11 research outputs found
Etude de la rĂ©activitĂ© de quelques allylphosphonates ÎČ-Ă©thoxycarbonylĂ©s
Due to the joint presence of several functional groups, ÎČ-ethoxycarbonylatedallylphosphonates are considered as excellent precursors for the preparation of neworganophosphorus compounds. In the presentwork, we first described the use of suchphosphonates as Michael acceptors. Indeed, weperformed conjugated additions of thiols,amines and enolate-anion under mild reactionconditions. Allylphosphonates were also usedfor the preparation of a new family of phosphonomethyl α,ÎČ-unsaturated Îł-lactams.The key step of this sequence is a conjugateaddition of nitroalkanes on allylphosphonates followed by a Nef reaction. Ketoester intermediaites were then convertedinto lactams by reaction with primary amines.Pd-catalyzed arylations on allylphosphonates allowed preparing phosphonated heterocyclesderived from coumarin, quinolinone andbenzoxepinone skeletons. The synthesis of Pheterocyclesof various sizes fromallylphosphonates was explored by theconversion of phosphonate inphosphorochloridate. The reactivity of the latterwith amines, allowed isolation of a new familyof 5-,7-, 8- and 9-membered N,P-heterocycles.The synthesis of 6-membered P-heterocycleshas also been described by performingcyclization under the conditions of a ringclosing metathesis (RCM) starting from bisallylphosphonates and bisallylphosphoramidates.La prĂ©sence conjointe de plusieurs fonctions confĂšre aux allylphosphonates ÎČ-Ă©thoxycarbonylĂ©s une rĂ©activitĂ© particuliĂšre. Ces derniers sont considĂ©rĂ©s comme dâexcellents prĂ©curseurs pour lâaccĂšs Ă de nouveaux composĂ©s organophosphorĂ©s. Dans le prĂ©sent travail, nous avons dĂ©crit, dans un premier temps, lâutilisation de ces adduits entant quâaccepteurs de Michael. En effet, nous avons effectuĂ© des additions conjuguĂ©es d ethiols, dâamines et dâanions Ă©nolates dans des conditions rĂ©actionnelles douces. Ces allylphosphonates ont Ă©tĂ© Ă©galement utilisĂ©s pour la prĂ©paration dâune nouvelle famille de Îł-lactames α,ÎČ-instaurĂ©s phosphono-mĂ©thylĂ©s.LâĂ©tape clĂ© de cette synthĂšse est une addition conjuguĂ©e de nitroalcanes sur les allylphosphonates suivie dâune rĂ©action de Nef..Les cĂ©toesters ainsi obtenus sont convertis en lactames par action dâamines primaires. Des rĂ©actions dâarylations pallado-catalysĂ©es sur les allyphosphonates ont permis lâaccĂšs Ă des hĂ©tĂ©rocycles phosphonatĂ©s dĂ©rivant de lacoumarine, de la quinolĂ©ine et de la benzoxĂ©pinone. La synthĂšse de P-hĂ©tĂ©rocyclesde diffĂ©rentes tailles Ă partir des allylphosphonates a Ă©tĂ© aussi possible par la conversion du groupe phosphonate en phosphorochloridate. La rĂ©activitĂ© de ce dernier vis-Ă -vis de diffĂ©rentes amines, a permis dâisoler une nouvelle famille de N,PhĂ©tĂ©rocyclesĂ 5, 7, 8 et 9 chaĂźnons. La synthĂšse de P-hĂ©tĂ©rocycles Ă 6 chainons a Ă©tĂ© Ă©galement dĂ©crite en rĂ©alisant des cyclisations dans les conditions de mĂ©tathĂšse cyclisante (RCM) Ă partir dâun bisallylphosphonate et dâun bisallylphosphoramidate issus des mĂȘmes prĂ©curseurs
Study of the reactivity of some ÎČ-ethoxycarbonylated allylphosphonates
La prĂ©sence conjointe de plusieurs fonctions confĂšre aux allylphosphonates ÎČ-Ă©thoxycarbonylĂ©s une rĂ©activitĂ© particuliĂšre. Ces derniers sont considĂ©rĂ©s comme dâexcellents prĂ©curseurs pour lâaccĂšs Ă de nouveaux composĂ©s organophosphorĂ©s. Dans le prĂ©sent travail, nous avons dĂ©crit, dans un premier temps, lâutilisation de ces adduits entant quâaccepteurs de Michael. En effet, nous avons effectuĂ© des additions conjuguĂ©es d ethiols, dâamines et dâanions Ă©nolates dans des conditions rĂ©actionnelles douces. Ces allylphosphonates ont Ă©tĂ© Ă©galement utilisĂ©s pour la prĂ©paration dâune nouvelle famille de Îł-lactames α,ÎČ-instaurĂ©s phosphono-mĂ©thylĂ©s.LâĂ©tape clĂ© de cette synthĂšse est une addition conjuguĂ©e de nitroalcanes sur les allylphosphonates suivie dâune rĂ©action de Nef..Les cĂ©toesters ainsi obtenus sont convertis en lactames par action dâamines primaires. Des rĂ©actions dâarylations pallado-catalysĂ©es sur les allyphosphonates ont permis lâaccĂšs Ă des hĂ©tĂ©rocycles phosphonatĂ©s dĂ©rivant de lacoumarine, de la quinolĂ©ine et de la benzoxĂ©pinone. La synthĂšse de P-hĂ©tĂ©rocyclesde diffĂ©rentes tailles Ă partir des allylphosphonates a Ă©tĂ© aussi possible par la conversion du groupe phosphonate en phosphorochloridate. La rĂ©activitĂ© de ce dernier vis-Ă -vis de diffĂ©rentes amines, a permis dâisoler une nouvelle famille de N,PhĂ©tĂ©rocyclesĂ 5, 7, 8 et 9 chaĂźnons. La synthĂšse de P-hĂ©tĂ©rocycles Ă 6 chainons a Ă©tĂ© Ă©galement dĂ©crite en rĂ©alisant des cyclisations dans les conditions de mĂ©tathĂšse cyclisante (RCM) Ă partir dâun bisallylphosphonate et dâun bisallylphosphoramidate issus des mĂȘmes prĂ©curseurs.Due to the joint presence of several functional groups, ÎČ-ethoxycarbonylatedallylphosphonates are considered as excellent precursors for the preparation of neworganophosphorus compounds. In the presentwork, we first described the use of suchphosphonates as Michael acceptors. Indeed, weperformed conjugated additions of thiols,amines and enolate-anion under mild reactionconditions. Allylphosphonates were also usedfor the preparation of a new family of phosphonomethyl α,ÎČ-unsaturated Îł-lactams.The key step of this sequence is a conjugateaddition of nitroalkanes on allylphosphonates followed by a Nef reaction. Ketoester intermediaites were then convertedinto lactams by reaction with primary amines.Pd-catalyzed arylations on allylphosphonates allowed preparing phosphonated heterocyclesderived from coumarin, quinolinone andbenzoxepinone skeletons. The synthesis of Pheterocyclesof various sizes fromallylphosphonates was explored by theconversion of phosphonate inphosphorochloridate. The reactivity of the latterwith amines, allowed isolation of a new familyof 5-,7-, 8- and 9-membered N,P-heterocycles.The synthesis of 6-membered P-heterocycleshas also been described by performingcyclization under the conditions of a ringclosing metathesis (RCM) starting from bisallylphosphonates and bisallylphosphoramidates
Conception, Synthesis and In silico Assessment of New Morpholine-Containing Compounds Against Human Legumain and Cholinesterase Enzymes
International audienc
Recent advances in the chemistry of 1,2,4-triazoles: Synthesis, reactivity and biological activities
International audience1,2,4-Triazoles are important heterocyclic motifs that are widely found in molecular architectures with medicinal and pharmaceutical properties. Considering the importance of these scaffolds, many works have been published over the last few decades. This review provides a focus on the synthetic approaches towards 1,2,4-triazole derivatives from common precursors such as amidines, imidates, amidrazones, aryldiazoniums and hydrazones over the last decade. This review also aims to provide an overview of triazole derivatives biological properties within the last two years
On the Reactivity of N-Substituted Imidates Towards 1,4-Bisnucleophiles: An Experimental and Theoretical Study
International audienc
From imidates to vinyl-1,2,4-triazoles: Synthesis, mechanistic aspects and first issues of their reactivity
International audienc
Tuneable access to indole, indolone, and cinnoline derivatives from a common 1,4-diketone Michael acceptor
International audienceA convergent strategy is reported for the construction of nitrogen-containing heterocycles from common substrates: 1,4-diketones and primary amines. Indeed, by just varying substrates, substituents or heating mode it is possible to selectively synthesize indole, indolone (1,5,6,7-tetradihydroindol-4-one) or cinnoline (5,6,7,8-tetrahydrocinnoline) derivatives in moderate to excellent yields
Versatile approach to densely substituted isoxazolines and pyrazolines: Focus on a quaternary carbon center as a constitutive feature
International audienc
Îł-Alkylsulfide phosphonates through the thia-Michael strategy
<div><p>The formation of Îł-alkylsulfide phosphonates is described from allylphosphonates under mild conditions using thiols through the thia-Michael strategy. A series of new phosphonates, bisphosphonates were cleanly prepared in high yields. The methodology developed allowed further preparing Îł-alkylsulfide phosphonates bearing valuable esters groups in ÎČ and ÎŽ positions with respect to the phosphonate moiety.</p></div