Diastereomers of Cyclopropa[a]pyrrolizine Spiro-fused with a Benzo[4,5]imidazo[1,2-a]indole Fragment: Structure Determinations Using NMR Methods

Standard

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.

In: Applied Magnetic Resonance, Vol. 54, No. 10, 28.08.2023, p. 999-1014.

Research output: Contribution to journal › Conference article › peer-review

Author

Пронина, Юлия ; Степаков, Александр Владимирович ; Popova, Ekaterina A. ; Boitsov, Vitali M. ; Baichurin, Ruslan I. ; Селиванов, Станислав Иванович. / Diastereomers of Cyclopropa[a]pyrrolizine Spiro-fused with a Benzo[4,5]imidazo[1,2-a]indole Fragment: Structure Determinations Using NMR Methods. In: Applied Magnetic Resonance. 2023 ; Vol. 54, No. 10. pp. 999-1014.

BibTeX

@article{3519c917f09d484bafe11104bfb6e515,

title = "Diastereomers of Cyclopropa[a]pyrrolizine Spiro-fused with a Benzo[4,5]imidazo[1,2-a]indole Fragment: Structure Determinations Using NMR Methods",

abstract = "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.",

author = "Юлия Пронина and Степаков, {Александр Владимирович} and Popova, {Ekaterina A.} and Boitsov, {Vitali M.} and Baichurin, {Ruslan I.} and Селиванов, {Станислав Иванович}",

year = "2023",

month = aug,

day = "28",

doi = "10.1007/s00723-023-01608-w",

language = "English",

volume = "54",

pages = "999--1014",

journal = "Applied Magnetic Resonance",

issn = "0937-9347",

publisher = "Springer Nature",

number = "10",

note = "null ; Conference date: 27-03-2023 Through 30-03-2023",

}

RIS

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