344899-62-3Relevant academic research and scientific papers
Stereoselective approach to conjugated enone oximes from aliphatic nitro compounds and sulfur ylides
Akhmirov, Rauf T.,Ioffe, Sema L.,Yu. Sukhorukov, Alexey
, p. 686 - 689 (2021/11/26)
A novel approach to conjugated enone oximes from aliphatic nitro compounds deals with double silylation of N,N-bis(silyloxy) enamines followed by a stereoselective reaction with an ester-stabilized sulfur ylide. The proposed mechanism involves the generation of labile nitrosoalkenes as intermediates, which react with the sulfur ylide to give target enone oximes.
Synthesis of Isoxazolines from Nitroalkanes via a [4+1]-Annulation Strategy
Ushakov, Pavel Yu.,Khatuntseva, Elizaveta A.,Nelyubina, Yulia V.,Tabolin, Andrey A.,Ioffe, Sema L.,Sukhorukov, Alexey Yu.
supporting information, p. 5322 - 5327 (2019/11/13)
A novel access to isoxazolines was developed using the [4+1]-annulation of α-keto-stabilized sulfur ylides with N,N-bis(siloxy)enamines derived from aliphatic nitro compounds. The resulting 5-keto-substituted isoxazolines were shown to be convenient precursors of polysubstituted 3-hydroxypyrrolidines via the one-pot catalytic N?O hydrogenolysis/intramolecular reductive amination sequence. Application of this approach to the formal synthesis of Merck's potent NK1 receptor antagonist was demonstrated. (Figure presented.).
Addition of HO-Acids to N,N-Bis(oxy)enamines: Mechanism, Scope and Application to the Synthesis of Pharmaceuticals
Naumovich, Yana A.,Golovanov, Ivan S.,Sukhorukov, Alexey Yu.,Ioffe, Sema L.
supporting information, p. 6209 - 6227 (2017/11/15)
The regioselectivity of the addition of HO-acids to the activated π bond in N,N-bis(oxy)enamines has been found to be dramatically dependent upon the solvent. Mechanistic investigations and quantum-chemical calculations revealed that solvent affects the reaction pathway. In basic solvents (DMF, NMP, DMSO), N,N-bis(oxy)enamines were converted into nitrosoalkenes by a Lewis base promoted process followed by oxy-Michael addition of the HO-acid. In non-polar solvents (toluene, CH2Cl2), the reaction occurs by an acid-promoted SN′ substitution of the N-oxy-group via a highly reactive N-vinyl-N-alkoxynitrenium species. Based on these studies, general and efficient protocols for the oximinoalkylation of various HO-acids (carboxylic acids, phenols, hydroxamic, phosphoric and sulfonic acids) employing readily available N,N-bis(oxy)enamines were developed. These methods proved to be applicable to the post-modification of natural molecules bearing acidic OH groups (such as steroidal hormones, bile acids, protected amino acids and peptides) and ligands (BINOL). The resulting α-oxyoximes were demonstrated to be useful precursors of valuable 1,2-amino alcohol or 1,2-hydroxylamino alcohol derivatives, including the antiarrhythmic drug Mexiletine and a potent matrix metalloproteinase inhibitor.
A general metal-assisted synthesis of α-halo oxime ethers from nitronates and nitro compounds
Sukhorukov, Alexey Yu.,Kapatsyna, Maria A.,Yi, Tammy Lim Ting,Park, Hyeong Ryool,Naumovich, Yana A.,Zhmurov, Petr A.,Khomutova, Yulia A.,Ioffe, Sema L.,Tartakovsky, Vladimir A.
, p. 8148 - 8159 (2015/02/05)
An approach to the synthesis of α-halo oxime ethers from readily accessible nitronates and nitro compounds via bis-(oxy)enamines is reported. A key step of the strategy involves the unprecedented reaction of bis(oxy)enamines with a metal (Co, Zn, Mg, Mn)
Reaction of n,n-dioxyenamines with anhydrides of carboxylic and sulfonic acids; A new method for the synthesis of a-hydroxyoxime derivatives
Tabolin, Andrey A.,Lesiv, Alexey V.,Ioffe, Sema L.
scheme or table, p. 3099 - 3105 (2010/01/15)
The reactions of N,N-dioxyenamines with carboxylic and sulfonic acid anhydrides were investigated. A new method for the synthesis of a-hydroxyoxime derivatives via the reaction of N,N-dioxyenamines with trifluoroacetic anhydride is described.
The chemistry of N,N-bis(siloxy)enamines. Part 8. A general method for the preparation of α-azido oximes from aliphatic nitro compounds
Sukhorokov, Alexey Yu.,Bliznets, Igor V.,Lesiv, Alexey V.,Khomutova, Yulija A.,Strelenko, Yuriy A.,Ioffe, Sema L.
, p. 1077 - 1082 (2007/10/03)
A new strategy for the synthesis of α-azido oximes from aliphatic nitro compounds via interaction of N,N-bis(silyloxy)enamines with trimethylsilylazide was realized to give the target products with good yields.
