3551-51-7Relevant articles and documents
The Easy Approach to N -Hydroxy- N -cycloalkenylamides through Nitrosocarbonyl Ene Reactions to Cycloalkenes: Valuable Compounds for Antiviral Syntheses
Hameed, Karzan Khaleel,Amin, Ahmed Anwar,Hussain, Faiq H. S.,Memeo, Misal Giuseppe,Moiola, Mattia,Quadrelli, Paolo
, p. 1383 - 1390 (2019)
An easy approach to N -hydroxy- N -cycloalkenylamides, ene adducts of cyclic alkenes of different sizes, is presented. The products can be obtained both through the thermal generation of the nitrosocarbonyl intermediates and via the photochemical fragment
Titanium and Cobalt Bimetallic Radical Redox Relay for the Isomerization of N -Bz Aziridines to Allylic Amides
Wood, Devin P.,Guan, Weiyang,Lin, Song
, p. 4213 - 4220 (2021/08/10)
Herein a bimetallic radical redox-relay strategy is employed to generate alkyl radicals under mild conditions with titanium(III) catalysis and terminated via hydrogen atom transfer with cobalt(II) catalysis to enact base-free isomerizations of N-Bz aziridines to N-Bz allylic amides. This reaction provides an alternative strategy for the synthesis of allylic amides from alkenes via a three-step sequence to accomplish a formal transpositional allylic amination.
HYDROGEN BOND DIRECTED NITRILE OXIDE CYCLOADDITION REACTIONS OF ALLYLIC 2o-AMIDES
Curran, Dennis P.,Gothe, Scott A.,Choi, Sung-Mo
, p. 1371 - 1395 (2007/10/02)
The ability of allylic and homoallylic 2o-amides to direct nitrile oxide cycloaddition reactions has been studied.For N-cyclopentenyl amides, good regio- and stereochemical control are observed and mechanistic studies suggest that hydrogen bond
NOVEL THERMOLYTIC TRANSFORMATION OF N-BENZOYL 2-AZA 3-OXA BICYCLO(2.2.1)HEPT-5-ENE AND N-BENZOYL 2-AZA 3-OXA BICYCLO(2.2.1)-HEPTANE
Ranganathan, D.,Ranganathan, S.,Rao, C. B.
, p. 637 - 641 (2007/10/02)
Novel thermolytic pathways were encountered in careful studies with N-benzoyl 2-aza 3-oxa bicyclo(2.2.1)heptene (1) and N-benzoyl 2-aza 3-oxa bicyclo(2.2.1)heptane (2).Compound 1 thermally fragments by four pathways, namely, (3,3)-sigmatropic shift, (4+2)-cycloreversion, N-O rupture and C-N homolysis.The (3,3)-sigmatropic shift provides a novel route to unusual, bicyclic heterocycles.Electron withdrawing aryl groupings tend to promote the (3,3)-sigmatropic shift pathway over others.The (4+2)-cycloreversion of 1 leads to nitroso carbonyl benzene and cyclopentadiene.The weak ? bonds of PhCONO undergo ready homolysis.The intermediate arising from N-O rupture leads to a cyclopentenone radical similar to that involved in the PG endoperoxide -> PGE change.This radical either combines with benzoyl radical leading to 4-dibenzoylamino cyclopentenone or is transformed to an enamide by loss of hydrogen.The N-O rupture leads to the formation of benzanilide.Nitrosocarbonyl benzene is a powerful electrophile.With cyclohexene it forms a hydroximic ester, initiated by nucleophile acceptance at the CO oxygen.In contrast, it reacts with P(OMe)3 leading to diphenylurea via nucleophile acceptance at N=O oxygen.Thermolysis of 2 proceeds largely by N-O rupture, similar to that normally observed in the PG endoperoxide -> PGE change.
