133609-18-4Relevant articles and documents
Organocatalytic Radical Involved Oxidative Cross-Coupling of N-Hydroxyphthalimide with Benzylic and Allylic Hydrocarbons
Dian, Longyang,Wang, Sisi,Zhang-Negrerie, Daisy,Du, Yunfei
, p. 3836 - 3842 (2015)
The cross-coupling reaction between N-hydroxyphthalimide and various benzylic and allylic hydrocarbons was realized through an organocatalytic radical-mediated process involving C(sp3)-O bond formation using tert-butyl hydroperoxide (t-BuOOH) as an oxidant and tetra-n-butylammonium iodide [(n-Bu]4NI] as a catalyst, during which the phthalimide N-oxyl (PINO) radical and benzylic and allylic radicals were generated in situ and underwent the selective radical/radical cross-coupling reaction. This novel method provides a convenient metal-free approach to the synthesis of O-alkylated hydroxy imides under mild reaction conditions.
O-Isocyanates as Uncharged 1,3-Dipole Equivalents in [3+2] Cycloadditions
Allen, Meredith A.,Beauchemin, André M.,Ivanovich, Ryan A.
supporting information, p. 23188 - 23197 (2020/10/12)
1,3-Dipoles are commonly used in [3+2] cycloadditions, whereas isoelectronic uncharged dipole variants remain underdeveloped. In contrast to conventional 1,3-dipoles, uncharged dipole equivalents form zwitterionic cycloadducts, which can be exploited to build further molecular complexity. In this work, the first cycloadditions of oxygen-substituted isocyanates (O-isocyanates) were studied experimentally and by DFT calculations. This unique cycloaddition strategy provides access to a novel class of heterocycle aza-oxonium ylides through intramolecular and intermolecular cycloadditions with alkenes. This allowed a systematic study of the reactivity of the transient aza-oxonium ylide intermediate, which can undergo N?O bond cleavage followed by nitrene C?H insertion, and the formation of β-lactams or isoxazolidinones upon varying the structure of the alkene or O-isocyanate reagents.
A new supported reagent for the parallel synthesis of primary and secondary O-alkyl hydroxylamines through a base-catalyzed Mitsunobu reaction
Maillard, Ludovic T.,Benohoud, Meryem,Durand, Philippe,Badet, Bernard
, p. 6303 - 6312 (2007/10/03)
The growing field of applications of O-alkyl hydroxylamines in medicinal chemistry and chemical biology has motivated the search for a parallel synthesis. A solid-phase approach based on the alkylation by alcohols of a new supported N-hydroxyphthalimide reagent using a Mitsunobu reaction followed by methylaminolysis has been optimized. This study points out the importance of the linker and a specific base effect for the Mitsunobu reaction. A large variety of alcohols can be used to give with moderate to high yields diverse O-alkyl hydroxylamines in high purity.
Capture-ROMP-release: application for the synthesis of O-alkylhydroxylamines.
Harned, Andrew M,Hanson, Paul R
, p. 1007 - 1010 (2007/10/03)
[reaction: see text] A new capture-ROMP-release method for chromatography-free purification of N-hydroxysuccinimde Mitsunobu reactions is described. The Mitsunobu reaction captures a variety of alcohols onto a norbornenyl N-hydroxysuccinimide monomer. Subjection of the resulting crude reaction mixture to ROM-polymerization generates a polymer that can be precipitated with methanol and filtered from the Mitsunobu byproducts. Treatment of the polymer with hydrazine releases the substrate from the water-soluble polymer, producing a variety of O-alkylhydroxylamines with good purity.
2-(4,6-dimethoxy-2-pyrimidinyloxy)benzaldoximes, preparation processes thereof, herbicides containing the same, and herbicidal compositions containing the same along with other active ingredient
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, (2008/06/13)
Disclosed are herbicidally active pyrimidine derivatives of the formula STR1 wherein R represents a hydrogen atom or an etherifying group, e.g., a lower alkyl, lower alkenyl, lower alkynyl, phenyl-substituted lower alkenyl, lower haloalkenyl, cycloalkyl, substituted phenyl-substituted lower alkenyl or phenyl-substituted lower alkynyl group; or a group represented by the following formula: STR2 wherein R1 represents a hydrogen atom or a lower alkyl group, X a halogen atom or a lower alkyl or lower alkoxyl group, m and n individually 0-2, and when m is 2, both Xs may be the same or different, and herbicidal compositions containing the same, alone or in combination with another herbicidally active compound, the pyrimidine derivatives being prepared by reaction of 2-(4,6-dimethoxy-2-pyrimidinyloxy)benzaldehyde with NH2 OR or with a salt of hydroxylamine followed by reaction with a halide of the formula RY wherein R has the same value as above and Y is Cl, Br or I.
