15922-50-6Relevant academic research and scientific papers
Solvent dependency of the yield of an N-monosubstituted diaziridine: A GC-MS study
Billing, Peter,Brinker, Udo H.
experimental part, p. 2822 - 2824 (2012/07/27)
Due to the growing importance of diaziridines in the drug design and the increasing popularity of diazirines as carbene precursors, the solvent influence on the yield of an N-monosubstituted diaziridine has been studied. It was observed that data points w
Bond rotation dynamics of N-cycloalkenyl-N-benzyl α-haloacetamide derivatives
Guthrie, David B.,Damodaran, Krishnan,Curran, Dennis P.,Wilson, Paul,Clark, Andrew J.
supporting information; experimental part, p. 4262 - 4266 (2009/09/08)
(Chemical Equation Presented) Barriers to rotation of the N-alkenyl bond in a series of N-cycloalkenyl-N-benzyl α-haloacetamide derivatives have been measured by variable-temperature NMR experiments. The barriers range from 10 to 18 kcal/mol, depending on ring size and on substituents on the cycloalkene and the amide. The observed trends aid in the design of substituent combinations that provide resolvable enantiomers or diastereomers at ambient temperature. The compounds undergo 4-exo and 5-endo radical cyclizations at rates that may be faster or slower than the estimated rate of N-alkenyl bond rotation in the derived radicals, depending on the substituents.
An improved and stereoselective route to all-cis-2,6-disubstituted 4-hydroxypiperidines from accessible 4-substituted 4-N-benzylaminobut-1-enes
Varlamov, Alexey,Kouznetsov, Vladimir,Zubkov, Fedor,Chernyshev, Alexey,Shurupova, Olga,Vargas Mendez, Leonor Y.,Palma Rodriguez, Alirio,Rivero Castro, Juliette,Rosas-Romero, Alfredo J.
, p. 771 - 783 (2007/10/03)
The reaction between allylmagnesium bromide and imines 5a-l leads to the corresponding 4-substituted 4-N-benzylaminobut-1-enes 6a-1, which were oxidized in a regioselective manner to the alkenylnitrones 7a-l. The intramolecular 1,3-dipolar cycloaddition of these nitrones gave 2-spiroannulated or 2-substituted 6-exo-phenyl-1-aza-7-oxabicyclo[2.2.1]heptanes 8a-j. Reductive cleavage of the N-O bond of the obtained bicycles afforded the diverse substituted 4-hydroxypiperidines 9a-h in good yields. This stereoselective approach allowed the preparation of all-cis-4-hydroxy-6-phenyl-2-nonylpiperidine (9i), a close analogue of dendrobatid frog alkaloid 241D.
Influence of copper(II) acetate on Ni/AcOH-promoted 5-endo and 5-exo radical cyclisations of trichloroacetamides
Cassayre, Jér?me,Dauge, Delphine,Zard, Samir Z.
, p. 471 - 474 (2007/10/03)
Incorporation of Cu(OAc)2 as oxidant in Ni/AcOH-promoted 5-endo radical cyclisations of N-alkenyl-trichloroacetamides allows an interesting control of the oxidation level of the products, as illustrated by the conversion of 3 into either 4 or 5. In addition, allylic trichloroacetamides 13a-f under the same conditions underwent a 5-exo radical cyclisation-oxidation sequence leading to unsaturated hydroindolones, which represent valuable synthetic intermediates.
Synthesis of new spiro-N-heterocycles with cyclooctane fragment from N- (1-alkenylcyclooctyl)-N-aryl(benzyl) amines
Vargas, Leonor M.,Rozo, Wilson,Kouznetsov, Vladimir
, p. 785 - 796 (2007/10/03)
The homoallylic amines (6-10) derived from N-cyclooctylidenearyl (benzyl)amines and allyl- or prenylmagnesium bromides as organometallic reagents have been used for synthesis of spiro-N-heterocycles. The tetrahydrospiro[3H-2-benzazepine-3,1'-cyclooctanes] (11 and 12) have been obtained from the homoallylamines (6 and 7) under acidic conditions. The tetrahydro-1-benzazepine (15) spiroannulated with a cyclooctane moiety has been prepared by treating the homoallylic amine (9) with conc. sulfuric acid. Treatment of the homoallylmine (6) with 92% sulfuric acid in chloroform at reflux afforded tetrahydrospiro[1,2,3-oxathiazine-2,2-dioxide-4,1'- cyclooctane] (17). The latter has been converted into 1-benzyl-4- methylspiro[azetidine-2,1'-cyclooctane] (18). The homoallylamine (6) has been cyclized into the 1-benzylspiro[pyrrolidine-2,1'-cyclooctane] (19).
Chemistry of functionalized benzazepines. 5 [1]. Synthesis and chemical transformation of the 1,2,4,5-tetrahydrospiro [3H-2-benzazepine-3,1'- cycloalkanes]
Kouznetsov,Palma,Salas,Vargas,Zubkov,Varlamov,Martinez
, p. 1591 - 1595 (2007/10/03)
The synthesis of new spiro derivatives of tetrahydro-2-benzazepine was accomplished and their nitration, bromination, allylation, acetylation, formylation and oxidation reactions were studied. Nitration and bromination of 5-methyl(1-5-dimethyl)-1,2,4,5-te
Enamine Chemistry. Part 36. Alkylation of Imines of Medium-Large Ring Ketones with Electrophilic Alkenes
Hickmott, Peter W.,Jutle, Kasturi K.,Pienar, Daniel H.
, p. 2399 - 2402 (2007/10/02)
The alkylation of the benzylamine imines of cycloheptanone, cyclo-octanone, and cyclododecanone with acrylonitrile, methyl acrylate, methyl vinyl sulphone, phenyl vinyl ketone, and phenyl vinyl sulphone, has been studied.The course of the reaction is surp
THE SYNTHESIS OF SPIROCYCLIC COMPOUNDS BY REGIOSPECIFIC PALLADIUM CATALYSED CYCLISATION REACTIONS
Grigg, Ronald,Sridharan, Visuvanathar,Stevenson, Paul,Sukirthalingam, Sukanthini
, p. 3557 - 3568 (2007/10/02)
Enamides derived from o-iodobenzoic acid and Z-3-bromoacrylic acid undergo regiospecific palladium catalysed exo-trig cyclisation onto a proximate alkene to give spirocyclic products in good to excellent yield.Double bond isomerisation in the product is n
