22818-69-5Relevant articles and documents
Easy and direct conversion of tosylates and mesylates into nitroalkanes
Palmieri, Alessandr,Gabrielli, Serena,Ballini, Roberto
, p. 533 - 536 (2013)
Tosylates and mesylates were directly converted into the corresponding nitroalkanes, by their treatment with tetrabutylammonium nitrite (TBAN) under mild conditions.
Novel Regioselective Generation of Nitroalkane Dianions
Yamada, Kazutoshi,Tanaka, Seiji,Kohmoto, Shigeo,Yamamoto, Makoto
, p. 110 - 111 (1989)
An alteration of the regioselectivity in dianion formation, from the usual α,α-dianions to the uncommon α,β-dianions, of nitroethane and 1-nitropropane was established by changing the order of addition of reagents.
Ozone-Mediated Amine Oxidation and Beyond: A Solvent-Free, Flow-Chemistry Approach
Skrotzki, Eric A.,Vandavasi, Jaya Kishore,Newman, Stephen G.
, p. 14169 - 14176 (2021/06/30)
Ozone is a powerful oxidant, most commonly used for oxidation of alkenes to carbonyls. The synthetic utility of other ozone-mediated reactions is hindered by its high reactivity and propensity to overoxidize organic molecules, including most solvents. This challenge can largely be mitigated by adsorbing both substrate and ozone onto silica gel, providing a solvent-free oxidation method. In this manuscript, a flow-based packed bed reactor approach is described that provides exceptional control of reaction temperature and time to achieve improved control and chemoselectivity over this challenging transformation. A powerful method to oxidize primary amines into nitroalkanes is achieved. Examples of pyridine, C-H bond, and arene oxidations are also demonstrated, confirming the system is generalizable to diverse ozone-mediated processes.
Crystallization Does It All: An Alternative Strategy for Stereoselective Aza-Henry Reaction
Mar?eková, Michaela,Ger?a, Peter,?oral, Michal,Moncol, Ján,Berke?, Du?an,Kolarovi?, Andrej,Jakubec, Pavol
supporting information, p. 4580 - 4584 (2019/06/17)
An efficient and experimentally straightforward method for the stereoselective synthesis of a variety of β-nitro-α-amino carboxylic acids via aza-Henry (nitro-Mannich) reaction of aldimines is disclosed, yielding either anti- or a rarely reported syn-configuration. The reaction operates directly on free glyoxylic acid and generates imine species in situ. Crystallization-controlled diastereoselectivity enables isolation of the target compounds in high enantio- and diastereomeric purities by a simple filtration.
Autoinductive conversion of α,α-diiodonitroalkanes to amides and esters catalysed by iodine byproducts under O2
Li, Jing,Lear, Martin J.,Hayashi, Yujiro
supporting information, p. 6360 - 6363 (2018/06/21)
Studies to convert nitroalkanes into amides and esters using I2 and O2 revealed in situ-generated iodine species facilitate the homolytic C-I bond cleavage of α,α-diiodonitroalkanes, arguably in an autoinductive or autocatalytic manner. Consequently, we devised a rapid and economical I2/O2-based method to synthesise sterically hindered esters directly from primary nitroalkanes.
Unusual reactivity of nitronates with an aryl alkyl carbonate: Synthesis of α-amino esters
Reddy, Golipalli Ramana,Mukherjee, Debopreeti,Chittoory, Arjun Kumar,Rajaram, Sridhar
supporting information, p. 5874 - 5877 (2015/01/08)
The monoanions of nitroalkanes are ambident nucleophiles that react with carbonate electrophiles through the oxygen atom. Products arising from reactivity at the carbon atom will yield α-nitro esters, which are precursors for α-amino esters. We demonstrate this in the reactions of nitroalkanes with benzyl phenyl carbonate and DABCO where α-nitro esters are obtained instead of nitrile oxides. The products are readily reduced to α-amino esters. This pathway could be a safe alternative to the Strecker reaction.
Facile reduction of nitroarenes into anilines and nitroalkanes into hydroxylamines via the rapid activation of ammonia· borane complex by supported gold nanoparticles
Vasilikogiannaki, Eleni,Gryparis, Charis,Kotzabasaki, Vasiliki,Lykakis, Ioannis N.,Stratakis, Manolis
supporting information, p. 907 - 911 (2013/05/08)
Gold nanoparticles supported on titania catalyse, even at a ppm loading level, the quantitative reduction of nitroarenes into anilines and nitroalkanes into alkylhydroxylamines by the ammonia× borane complex. No dehalohalogenation was seen in the case of chloro- or bromonitroarenes, while ester, cyano, or carboxylic acid functionalities also remain intact. The nitroarene to aniline reduction pathway does not require nitrosoarenes as intermediate products. Copyright
INTERMEDIATE COMPOUNDS AND PROCESS FOR THE PREPARATION OF FINGOLIMOD
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Page/Page column 26, (2012/05/19)
The present invention relates to processes for the preparation of (2-Amino-2-[2-(4-octylphenyl)ethyl]propane-1,3-diol hydrochloride (Fingolimod) and pharmaceutically acceptable salts thereof, and intermediates formed in such processes.
METHODS AND COMPOUNDS FOR THE PREPARATION OF FLUORINE-LABELED DEOXY-FTY720
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Page/Page column 17, (2012/01/06)
Highly efficient processes for making radioactive and non-radioactive Fluorodeoxy- FTY720 are provided. Also provided are novel precursor compounds included in such processes. In addition the present invention prov ides compounds useful in the treatment a
