15922-50-6Relevant articles and documents
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
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.
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).