475983-77-8Relevant academic research and scientific papers
Functionalization of 2-(S)-isopropyl-5-iodo-pyrimidin-4-ones through Cu(I)-mediated 1,3-dipolar azide-alkyne cycloadditions
Stefani, Hélio A.,Amaral, M?nica F.Z.J.,Manarin, Flávia,Ando, R?mulo A.,Silva, Nathália C.S.,Juaristi, Eusebio
supporting information; scheme or table, p. 6883 - 6886 (2012/02/05)
A series of 2-(S)-isopropyl-pyrimidinones functionalized at C5 with triazole rings, in which the substituents are found at N-1′ of the triazole ring, were synthesized. Through the azide-acetylene cycloaddition reaction, using CuI as a copper source and ul
Synthesis of (2S)-isopropyl-5-alkynylpyrimidin-2-ones: Precursors of β-aminoacids
Stefani, Hélio A.,Amaral, Monica F.Z.J.,Juaristi, Eusebio
scheme or table, p. 1014 - 1019 (2011/03/21)
The efficient palladium-catalyzed Suzuki-Miyaura cross-coupling reaction of (2S)-isopropyl-5-iodo-2,3-dihydro-4(H)-pyrimidin-4-one with, arylethynyl-, heteroarylethynyl-, and alkylethynyltrifluoroborate salts is reported. The standard protocol was evaluat
Functionalization of (2S)-Isopropyl-5-iodo-2,3-dihydro-4(H)-pyrimidin-4- ones by a Suzuki-Miyaura Cross-Coupling Reaction Using Aryltrifluoroborate Salts: Convenient Enantioselective Preparation of α-Substituted β-Amino Acids
Stefani, Helio A.,Amaral, Monica F. Z. J.,Reyes-Rangel, Gloria,Vargas-Caporali, Jorge,Juaristi, Eusebio
experimental part, p. 6393 - 6403 (2011/02/21)
A simple protocol for the Pd(OAc)2-catalyzed cross-coupling reaction of 1-benzoyl-(2S)-isopropyl-5-iodo-2,3-dihydro-4(H)-pyrimidin-4-ones with potassium aryltrifluoroborates was developed. The reaction is performed at 110°C with a ligand-free catalyst. In all cases, complete conversion of the 1-benzoyl-(2S)-isopropyl-5-iodo-2,3-dihydro-4(H)-pyrimidin-4-onesand aryltrifluoroborates into the C-C coupling products was observed within 30-360 min. It is noteworthy that a largevariety of groups present in the potassium aryltrifluoroborates (-CF3, -OMe, -SEt, -CN, -CHO, -Cl, -Cbz, -NCbz,-OH, -CO2H) could be tolerated. Hydrogenation of the endocyclic double bonds in the Suzuki-Miyaura products followed by acid hydrolysis afforded highly enantioenrichedα-aryl-substituted β-amino acids. We present a general approach for the synthesis of (2S)-isopropyl-5-aryl-2,3- dihydro-4(H)-pyrimidin-4-ones by Suzuki-Miyaura reaction of aryltrifluoroborate salts with(2S)-isopropyl-5-iodo-2,3-dihydro-4(H)-pyrimidin-4-ones in the presence of a palladium catalyst and a base. The arylated compounds were transformed into enantioenriched α-aryl-substituted β-amino acids. Copyright
Synthesis of 2-substituted-5-halo-2,3-dihydro-4(H)-pyrimidin-4-ones and their derivatization utilizing the sonogashira coupling reaction in the enantioselective synthesis of α-substituted β-amino acids
Diaz-Sanchez, Blanca R.,Iglesias-Arteaga, Martin A.,Melgar-Fernandez, Roberto,Juaristi, Eusebio
, p. 4822 - 4825 (2008/02/05)
(Chemical Equation Presented) A convenient, one-pot procedure for the synthesis of 1-benzoyl-2(S)-substituted-5-iodo-2,3-dihydro-4(H)-pyrimidin-4-ones by tandem decarboxylation/β-iodination of the corresponding 6-carboxy-perhydropyrimidin-4-ones was devel
Tandem reactions initiated by the oxidative decarboxylation of 1-benzoyl-2(S)-tert-butyl-6(S)-carboxyperhydropyrimidin-4-one
Iglesias-Arteaga, Martín A.,Avila-Ortiz, C.Gabriela,Juaristi, Eusebio
, p. 5297 - 5300 (2007/10/03)
Treatment of the title perhydropyrimidinone with diacetoxyiodobenzene and iodine followed by addition of allyltrimethylsilane and boron trifluoride etherate afforded 1-benzoyl-2(S)-tert-butyl-2,3-dihydro-4(H)-pyrimidin-4-one in 65-71% yield, via an efficient three-step radical decarboxylation-oxidation-β-elimination tandem reaction. In contrast, when addition of allyltrimethylsilane/BF3·OEt2 was suppressed, a remarkable five-step tandem process led to the formation of vinylic iodide, 1-benzoyl-2(S)-tert-butyl-5-iodo-2,3-dihydro-4(H)-pyrimidin-4-one as the main product.
