195964-53-5Relevant articles and documents
C(sp3)?C(sp3) Bond Formation via Electrochemical Alkoxylation and Subsequent Lewis Acid Promoted Reactions
López, Enol,van Melis, Carlo,Martín, Raúl,Petti, Alessia,de la Hoz, Antonio,Díaz-Ortíz, ángel,Dobbs, Adrian P.,Lam, Kevin,Alcázar, Jesús
supporting information, p. 4521 - 4525 (2021/08/06)
A two-step transition metal-free methodology for the C(sp3)?C(sp3) functionalisation of saturated N-heterocyclic systems is disclosed. First, aminal derivatives are generated through the anodic oxidation of readily accessible carboxylic acids. Then, in the presence of BF3 ? OEt2, iminium ions are unmasked and rapidly alkylated by organozinc reagents under flow conditions. Secondary, tertiary and quaternary carbon centers have been successfully assembled using this methodology. Such an approach is especially relevant to drug discovery since it increases C(sp3)-functionalities rapidly within a molecular framework. As proof of concept, our methodology was applied to derivatization of peptides and an API. (Figure presented.).
Electrochemical Scaled-up Synthesis of Cyclic Enecarbamates as Starting Materials for Medicinal Chemistry Relevant Building Bocks
Tereshchenko, Oleksandr D.,Perebiynis, Maryana Y.,Knysh, Irina V.,Vasylets, Olesia V.,Sorochenko, Anna A.,Slobodyanyuk, Eugeniy Y.,Rusanov, Eduard B.,Borysov, Oleksandr V.,Kolotilov, Sergey V.,Ryabukhin, Sergey V.,Volochnyuk, Dmitriy M.
supporting information, p. 3229 - 3242 (2020/07/06)
The electrochemical Shono oxidation of Boc-protected cyclic amines was revised. The conditions for scalable electrochemical synthesis of cyclic enecarbamates were found. The developed protocol included recycling of the full range of used reagents, favoring to E-factor reduction according to Green Chemistry requirements. The method opened the way for the convenient preparation of previously uncommon materials, which could become useful synthetic intermediates. Their synthetic potential was evaluated in [2+1] and [2+2] cycloadditions as well as electrophilic functionalization. Moreover, functionalized enecarbamates with carbonyl groups in β-position were used as latent 1,3-bielectrophiles in classical heterocyclizations. In a case of the hydrazine, the corresponding unusually decorated pyrazoles were prepared. The proposed methodology is a straightforward tool for the design and synthesis of Medicinal Chemistry relevant building blocks. As examples, 5-fluoro pipecolic and 3-fluoro isonipecotic acids were synthesized starting from Boc-protected esters of the pipecolic and the isonipecotic acids respectively; the 5-step approach to pyrazole containing α-aminoacids with different linkers between the aminoacidic and pyrazole moieties was elaborated based on the cheapest commercially available racemic and chiral cyclic α-aminoacids; the convenient approach to the functionalized tetrahydropyrido[3,4-d]pyridazines was proposed starting from Boc-protected ester of the isonipecotic acids. (Figure presented.).
A Straightforward Synthesis of Six-Membered-Ring Heterocyclic α-Aminophosphonic Acids from N-Acyliminium Ions
Argüello-Velasco, Rubén Oswaldo,Sánchez-Mu?oz, Grecia Katherine,Viveros-Ceballos, José Luis,Ordó?ez, Mario,Kafarski, Pawel
, (2019/06/24)
A convenient synthesis of phosphonic analogues of pipecolic acid and its heterocyclic analogues is reported. The major step of the elaborated procedure is the introduction of the phosphonate group into the skeleton of the appropriate cyclic amide through N-acyliminium ions. The former ones were obtained by preparation of the hemiaminals or their methyl ethers from the N-protected cyclic amides. Finally, the reaction with trimethyl phosphite in the presence of BF3·OEt2 afforded the desired phosphonates, which were converted into phosphonic acids by the hydrolysis of phosphonate moiety with simultaneous cleavage of the nitrogen protecting groups.
Synthesis of 3-oxadiazolyl/triazolyl morpholines: Novel scaffolds for drug discovery
Tereshchenko, Alexander D.,Myronchuk, Julia S.,Leitchenko, Lena D.,Knysh, Irina V.,Tokmakova, Ganna O.,Litsis, Olena O.,Tolmachev, Andrey,Liubchak, Konstantin,Mykhailiuk, Pavel
, p. 750 - 757 (2017/01/16)
Synthesis of isomeric 3-oxadiazolyl/triazolyl morpholines was performed based on a common intermediate on the gram scale. The target compounds were designed as novel scaffolds for the medicinal chemistry. The key reaction was an electrochemical CH-oxidati
PYRIMIDYL CYCLOPENTANES AS AKT PROTEIN KINASE INHIBITORS
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Page/Page column 94-95, (2009/03/07)
The present invention provides compounds of Formula (I), including tautomers, resolved enantiomers, diastereomers, solvates, metabolites, salts and pharmaceutically acceptable prodrugs thereof. Also provided are methods of using the compounds of this invention as AKT protein kinase inhibitors and for the treatment of hyperproliferative diseases such as cancer.
Synthesis of new trialkylsilylmethyloxazinones via intramolecular trapping of β-silyl carbocations by an N-Boc group
Brocherieux-Lanoy, Sylvie,Dhimane, Hamid,Poupon, Jean-Christophe,Vanucci, Corinne,Lhommet, Gerard
, p. 2163 - 2165 (2007/10/03)
N-BoC amino ethers 1a-e when treated with allyltrialkylsilanes in the presence of TiCl4 afford the expected allylation compounds 2a-e and/or the unprecedented silylated oxazinones 3a-e or 4a-e.
