122664-89-5Relevant academic research and scientific papers
Substituent effect study on the experimental 13C NMR chemical shifts of 3-(substituted phenyl)-3a,4,8,8a-tetrahydro-1,3-dioxepino[5,6-d] [1,2] isoxazoles
Kara, Yesim S.,Yalduz, Sümeyye
, p. 158 - 165 (2019/05/22)
Novel heterocyclic derivatives containing isoxazole ring were synthesized by the 1,3-dipolar cycloaddition reaction of substituted nitrile oxides with cis-4,7-dihydro-1,3-dioxepin in the present study. These 3-(substituted phenyl)-3a,4,8,8a-tetrahydro-1,3
AN UNUSUAL TERT-BUTYLAMINE MEDIATED CONVERSION OF 6-ARYL-7-FORMYL-2,4,5,8-TETRAHYDRO-1,3-DIOXA-5-AZOCINES TO 1,2,3,6-TETRAHYDROPYRIMIDINE DERIVATIVES
Stibranyi, Ladislav,Fisera, Lubor,Kacer, Rastislav,Oremus, Vladimir,Mihulova, Martina
, p. 2502 - 2509 (2007/10/02)
An unexpected contraction of the 8-membered ring to a 6-membered one occurring when 6-aryl-7-formyl-2,4,5,8-tetrahydro-1,3-dioxa-5-azocines II were treated with tert-butylamine afforded 4-aryl-5-formyl-1-(1,1-dimethylethyl)-1,2,3,6-tetrahydropyrimidines III.Reaction conditions for the photorearrangement of chlorophenyl-substituted condensed isoxazolines I to II were worked out.The reaction sequence: 1,3-dipolar cycloaddition, photochemical rearrangement, treatment with tert-butylamine constitutes a new route to pyrimidine derivatives from 2H,4H,7H-1,3-dioxepine.
PHOTO-INDUCED REARRANGEMENT OF ISOXAZOLINES - A PATHWAY TO 2,4,5,8-TETRAHYDRO-1,3-DIOXA-5-AZOCINE DERIVATIVES
Fisera, Lubor,Oremus, Vladimir,Stibranyi, Ladislav,Timpe, Hans-Joachim,Matusova, Alena
, p. 1982 - 1993 (2007/10/02)
4-R-Substituted-8-X-phenyl-3,5,10-trioxa-9-azabicyclodec-8-enes (X = H, 4-CH3, 4-OCH3, 4-Cl, 4-Br, 4-F, 3-NO2, 3-Cl, 3-Br) have been prepared by cycloaddition of substituted benzenenitriloxides with 2-R-substituted 1,3-dioxep-5-enes (R = H, CH3, C6H5).A mixture of the endo and exo adducts is formed, if R is CH3 or C6H5.Their irradiation produces high yields of the title compounds as the single products.High selectivity of the photo-rearrangement is due to resonance stabilization of the biradical with p electrons of the oxygen atom.The quantum yields of the photoreaction vary from 0.02 to 0.04 depending on the substituent X.An unexpected dependence has been found between the quantum yield of the photo-rearrangement and stereochemical arrangement of the 4-R-substituent: exo derivatives exhibit higher values than the endo derivatives.Also different are UV spectra of the endo and exo derivatives.A new synthesis principle is described enabling preparation of (n+1)-membered heterocycles from n-membered heterocycles.
PHOTOINDUZIERTE UMLAGERUNG VON ISOXAZOLINEN: SYNTHESEWEG ZU 2,4,5,8-TETRAHYDRO-1,3-DICX-5-AZOCINEN
Fisera, L.,Stibranyi, L.,Matusova, A.,Cremus, V.,Timpe, H.-J.
, p. 2731 - 2734 (2007/10/02)
A high yield 2,4,5,8-tetrahydro-1,3-diox-5-azocine synthesis, which employs a sequence of cycloaddition and photoinduced rearrangement has been developed.
