1222558-29-3Relevant academic research and scientific papers
Sequential Two-Step Stereoselective Amination of Allylic Alcohols through the Combination of Laccases and Amine Transaminases
Albarrán-Velo, Jesús,Lavandera, Iván,Gotor-Fernández, Vicente
, p. 200 - 211 (2020)
A sequential two-step chemoenzymatic methodology for the stereoselective synthesis of (3E)-4-(het)arylbut-3-en-2-amines in a highly selective manner and under mild reaction conditions is described. The approach consists of oxidation of the corresponding racemic alcohol precursors by the use of a catalytic system made up of the laccase from Trametes versicolor and the oxy-radical TEMPO, followed by the asymmetric reductive bio-transamination of the corresponding ketone intermediates. Optimisation of the oxidation reaction, exhaustive amine transaminase screening for the bio-transaminations and the compatibility of the two enzymatic reactions were studied in depth in search of a design of a compatible sequential cascade. This synthetic strategy was successful and the combinations of enzymes displayed a broad substrate scope, with 16 chiral amines being obtained in moderate to good isolated yields (29–75 %) and with excellent enantiomeric excess values (94 to >99 %). Interestingly, both amine enantiomers can be achieved, depending on the selectivity of the amine transaminase employed in the system.
Palladium(II)-Catalyzed Substituted Pyridine Synthesis from ?±,?-Unsaturated Oxime Ethers via a C-H Alkenylation/Aza-6?-Electrocyclization Approach
Yamada, Takahiro,Hashimoto, Yoshimitsu,Tanaka, Kosaku,Morita, Nobuyoshi,Tamura, Osamu
supporting information, p. 1659 - 1663 (2021/03/03)
An efficient synthetic method for multisubstituted pyridines from β-aryl-substituted α,β-unsaturated oxime ethers and alkenes via Pd-catalyzed C-H activation has been developed. Systematic optimization of catalyst ligands revealed that sterically hindered
Catalyst free synthesis of mono- and disubstituted pyrimidines from O-acyl oximes
Upare, Atul,Sathyanarayana, Pochampalli,Kore, Ranjith,Sharma, Komal,Bathula, Surendar Reddy
supporting information, p. 2430 - 2433 (2018/05/23)
Transition-metal or iodine catalyzed transformations of O-acyl oximes to various N-heterocycles are well established. Herein, we report a catalyst free, oxime carboxylate based, three-component condensation method to access mono- and disubstituted pyrimidines. A broad range of substituted pyrimidines were prepared in moderate to excellent yields. Control experiments reveal that in situ generated formamidine is the key intermediate.
Synthesis and anti-inflammatory activity of novel (substituted)benzylidene acetone oxime ether derivatives: Molecular modeling study
El-Gamal, Mohammed I.,Bayomi, Said M.,El-Ashry, Saadia M.,Said, Shehta A.,Abdel-Aziz, Alaa A.-M.,Abdel-Aziz, Naglaa I.
body text, p. 1403 - 1414 (2010/06/12)
Herein, we report the design, synthesis, and pharmacological properties of a series of substituted benzylidene acetone oxime ether derivatives from the corresponding oxime derivatives. All the newly synthesized compounds were investigated in vivo for their anti-inflammatory activities using carrageenin-induced rat paw oedema model. Among the compounds examined, compounds 5b and 7a showed the highest activity, nearly equivalent to that of the standard drug diclofenac sodium. Hence, they were screened for their analgesic activities using acetic acid-induced writhing model in mice and also, their ulcerogenic effects were studied. Compound 7a was found to possess significant anti-inflammatory and analgesic activities with negligible ulcerogenic effect. Docking study of the synthesized compound 7a into the active site of COX-1 and COX-2 revealed a similar binding mode to SC-558, a selective COX-2 inhibitor.
Convenient synthesis of 3,5-disubstituted isoxazoles
Kurangi, Reshma F.,Kawthankar, Rima,Sawal, Sulfala,Desai, Vidya G.,Tilve, Santosh G.
, p. 587 - 589 (2007/10/03)
α,β-Unsaturated oximes obtained from the corresponding α,β-unsaturated ketones on treatment with 2 equivalents of manganese dioxide in refluxing chloroform gives 3,5-disubstituted isoxazoles in good yields. Copyright Taylor & Francis Group, LLC.
