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1.
Joseph I. Degraw Lawrence F. Kelly Roy L. Kisliuk Yvette Gaumont Francis M. Sirotnak 《Journal of heterocyclic chemistry》1982,19(6):1587-1588
A synthesis of 8,10-dideazaminopterin, using 2,4-diamino-6-bromomethyl-8-deazapteridine ( 2 ) as a key intermediate, is described. Condensation of the triphenylphosphinylide derived from 2 with p-formylbenzoyl-L-glutamate afforded a 9,10-dehydro-8,10-dideazaminopterin ester intermediate 5 . Hydrogenation of the olefinic linkage and subsequent hydrolysis of the glutamate ester gave the title compound. 8,10-Dideazaminopterin was a potent growth inhibitor of folate dependent bacteria. It was 16 times more potent then methotrexate as an inhibitor of dihydrofolate reductase derived from L1210 leukemia cells, and showed strong activity against L1210 in mice. 相似文献
2.
The synthesis of alkylarylphosphines is easily carried out by hydrophosphination of unactivated alkenes under mild thermal activation; gram scale amounts of products can be prepared by this simple methodology. 相似文献
3.
Dr. Julien Gasnot Clément Botella Dr. Sébastien Comesse Dr. Sami Lakhdar Dr. Carole Alayrac Prof. Annie-Claude Gaumont Prof. Vincent Dalla Dr. Catherine Taillier 《Angewandte Chemie (Weinheim an der Bergstrasse, Germany)》2020,132(29):11867-11871
Advances in the field of phosphorus chemistry are documented, by revealing the synthetic utility of previously underutilized quaternary phosphiranium salts (QPrS) as three-chain-atom electrophilic building blocks. Notably, control of their challenging C-centered electrophilicity is disclosed with an expedient synthesis of tertiary β-anilino phosphines as a proof-of-concept. 相似文献
4.
Mihaela Gulea Małgorzata Kwiatkowska Piotr Łyżwa Remi Legay Annie-Claude Gaumont Piotr Kiełbasiński 《Tetrahedron: Asymmetry》2009,20(3):293-297
The Michael addition of selected sulfur and nitrogen nucleophiles to a chiral non-racemic 2-phosphono-2,3-didehydrothiolane S-oxide is fully diastereoselective. The enantiomeric excesses of the adducts obtained could be determined by 31P NMR spectroscopy using (R)-(+)-tert-butyl(phenyl)phosphinothioic acid as a chiral solvating agent. The addition of thiophenol was monitored by 31P NMR spectroscopy which made it possible to observe the formation and evolution of the kinetic and thermodynamic adducts in the reaction mixture. The structures of both enantiomeric thiophenol adducts have been determined by X-ray analysis. 相似文献
5.
Joseph I. Degraw Hiroaki Tagawa Pamela H. Christie John A. Lawson Edward G. Brown Roy L. Kisliuk Yvette Gaumont 《Journal of heterocyclic chemistry》1986,23(1):1-4
The synthesis of 5,10-dideazaaminopterin by two independent routes is described. Condensation of the piperidine enamine of 4-p-carbomethoxyphenylbutyraldehyde ( 4 ) with ethoxymethylenemalononitrile followed by treatment of the resultant arylethylenaminomalononitrile ( 5 ) with methanolic ammonia produced 2-amino-3-cyano-5-p-carbomethoxyphenethylpyridine ( 6 ). Cyclization of the aminocyanopyridine with guanidine afforded 4-amino-4-deoxy-5,10-dideazapteroic acid ( 8 ). Coupling of the pteroate intermediate with glutamate yielded the target 5,10-dideazaaminopterin ( 10 ). Alternatively, reduction of 2,4-diamino-6-formyl-5-deazapteridine ( 11 ) with sodium borohydride gave the 6-hydroxymethyl compound 12 . Conversion to the bromide was followed by alkylation of dimethyl homoterephthalate to afford methyl 4-amino-4-deoxy-10-carbomethoxy-5,10-dideazapteroate ( 14 ). Decarboxylation with ester cleavage (sodium cyanide in dimethyl sulfoxide at 180°) also gave the diaminopteroic acid ( 8 ). 5,10-dideazaaminopterin ( 10 ) was an effective growth inhibitorof folate dependent bacteria, S. faecium and L. casei. 相似文献
6.
Piotr ?y?wa Ma?gorzata Kwiatkowska Piotr Kie?basiński Alexander Betz Annie-Claude Gaumont 《Tetrahedron letters》2007,48(3):351-355
A chiral racemic 2-phosphono-2,3-didehydrothiolane sulfoxide was used as a Michael acceptor in the reactions with several nucleophiles, in particular thiols. In most cases the reactions were fully diastereoselective. The relative configuration of the resulting adducts was determined. 相似文献
7.
Join B Mimeau D Delacroix O Gaumont AC 《Chemical communications (Cambridge, England)》2006,(30):3249-3251
Preliminary results dealing with the synthesis of non-racemic P-stereogenic vinylphosphine-boranes by hydrophosphination of alkynes in the presence of a chiral catalyst are reported. 相似文献
8.
Recent results on the selective reduction of cyclic vinylphosphine oxides and vinylphosphinates, as well as their refunctionalization by the use of borane, are summarized. The selective reduction of the phosphorus moiety of unsaturated phosphonates, phosphinates, and phosphine oxides is also discussed. © 2001 John Wiley & Sons, Inc. Heteroatom Chem 12:161–167, 2001 相似文献
9.
Julien Gasnot Clment Botella Sbastien Comesse Sami Lakhdar Carole Alayrac Annie‐Claude Gaumont Vincent Dalla Catherine Taillier 《Angewandte Chemie (International ed. in English)》2020,59(29):11769-11773
Advances in the field of phosphorus chemistry are documented, by revealing the synthetic utility of previously underutilized quaternary phosphiranium salts (QPrS) as three‐chain‐atom electrophilic building blocks. Notably, control of their challenging C‐centered electrophilicity is disclosed with an expedient synthesis of tertiary β‐anilino phosphines as a proof‐of‐concept. 相似文献
10.
David Guérin Isabelle Dez Annie-Claude Gaumont Xavier Pannecoucke Samuel Couve-Bonnaire 《Comptes Rendus Chimie》2018,21(8):740-748
This study reports the ring-closing metathesis reaction of bisolefins, including a reluctant fluoroalkenes, linked with oxaza moiety. The resulting heterocycles were produced in high yields under high diluting conditions disfavoring the homodimerization side reaction of nonfluorinated double bond. The use of a mixture of solvents proved to be a good strategy to obtain the fluorinated heterocycles in fair to excellent yields. 相似文献