Результаты исследований: Научные публикации в периодических изданиях › статья в журнале по материалам конференции › Рецензирование
Diastereomers of Cyclopropa[a]pyrrolizine Spiro-fused with a Benzo[4,5]imidazo[1,2-a]indole Fragment: Structure Determinations Using NMR Methods. / Пронина, Юлия ; Степаков, Александр Владимирович; Popova, Ekaterina A.; Boitsov, Vitali M.; Baichurin, Ruslan I.; Селиванов, Станислав Иванович.
в: Applied Magnetic Resonance, Том 54, № 10, 28.08.2023, стр. 999-1014.Результаты исследований: Научные публикации в периодических изданиях › статья в журнале по материалам конференции › Рецензирование
}
TY - JOUR
T1 - Diastereomers of Cyclopropa[a]pyrrolizine Spiro-fused with a Benzo[4,5]imidazo[1,2-a]indole Fragment: Structure Determinations Using NMR Methods
AU - Пронина, Юлия
AU - Степаков, Александр Владимирович
AU - Popova, Ekaterina A.
AU - Boitsov, Vitali M.
AU - Baichurin, Ruslan I.
AU - Селиванов, Станислав Иванович
PY - 2023/8/28
Y1 - 2023/8/28
N2 - NMR spectroscopy methods have been used to prove structures of two diastereomers of cyclopropa[a]pyrrolizine spiro-fused with a benzo[4,5]imidazo[1,2-a]indole fragment which were obtained through a three-component 1,3-dipolar cycloaddition reaction and isolated in a ratio of 6:1. Complete signal assignment in 1H and 13C spectra of each compound was made by using some homonuclear (COSY, NOESY) and heteronuclear (HMQC, HMBC) NMR experiments. The spatial structure of the studied diastereomers was proved on the basis of data on interproton through-space interactions obtained from the NOESY spectra at a mixing time of 0.5 s. The comparison of the experimental and calculated values of the vicinal constants and interproton distances indicates that each of the studied diastereomers in solution is characterized by a fast (in the NMR time scale) conformational equilibrium due to the inversion of the nitrogen atom in the cyclopropa[a]pyrrolizine fragment.
AB - NMR spectroscopy methods have been used to prove structures of two diastereomers of cyclopropa[a]pyrrolizine spiro-fused with a benzo[4,5]imidazo[1,2-a]indole fragment which were obtained through a three-component 1,3-dipolar cycloaddition reaction and isolated in a ratio of 6:1. Complete signal assignment in 1H and 13C spectra of each compound was made by using some homonuclear (COSY, NOESY) and heteronuclear (HMQC, HMBC) NMR experiments. The spatial structure of the studied diastereomers was proved on the basis of data on interproton through-space interactions obtained from the NOESY spectra at a mixing time of 0.5 s. The comparison of the experimental and calculated values of the vicinal constants and interproton distances indicates that each of the studied diastereomers in solution is characterized by a fast (in the NMR time scale) conformational equilibrium due to the inversion of the nitrogen atom in the cyclopropa[a]pyrrolizine fragment.
UR - https://link.springer.com/article/10.1007/s00723-023-01608-w
UR - https://www.mendeley.com/catalogue/fc711964-8487-344e-8f05-13bb629163b0/
U2 - 10.1007/s00723-023-01608-w
DO - 10.1007/s00723-023-01608-w
M3 - Conference article
VL - 54
SP - 999
EP - 1014
JO - Applied Magnetic Resonance
JF - Applied Magnetic Resonance
SN - 0937-9347
IS - 10
Y2 - 27 March 2023 through 30 March 2023
ER -
ID: 108620420