TY  - JOUR
A1  - Barta, Petra
A1  - Szatmari, Istvan
A1  - Fueloep, Ferenc
A1  - Heydenreich, Matthias
A1  - Koch, Andreas
A1  - Kleinpeter, Erich
T1  - Synthesis and stereochemistry of new naphth[1,3]oxazino[3,2-a] benzazepine and naphth[1,3]oxazino[3,2-e]thienopyridine derivatives
JF  - Tetrahedron
N2  - Through the reactions of 1- or 2-naphthol and 4,5-dihydro-3H-benz[c]azepine or 6,7-dihydrothieno[3,2-c]pyridine, new aminonaphthol derivatives were prepared. The syntheses were extended by using N-containing naphthol analogues such as 5-hydroxyisoquinoline and 6-hydroxyquinoline. The ring closures of the novel bifunctional compounds were also achieved, resulting in new naphth[2,1-e][1,3]oxazines, naphth[1,2-e][1,3]oxazines, isoquinolino[5,6-e][1,3]oxazines and quinolino[5,6-e][1,3]oxazines. H-1 NMR spectra of the target heterocycles 16, 20 and 21 were sufficiently resolved to indentify the present stereochemistry; therefore, beside computed structures, spatial experimental (dipolar coupling-NOE) and computed (ring current effect of the naphthyl moiety-TSNMRS) NMR studies were employed. The studied heterocycles exist exclusively as S(14b),R(N), R(14b),S(N), and S(16b)S(N) isomers, respectively. The flexible moieties of the studied compounds prefer. (C) 2016 Elsevier Ltd. All rights reserved.
KW  - Modified Mannich reaction
KW  - Thienopyridine
KW  - Benzazepine
KW  - NMR spectroscopy
KW  - Stereochemistry
KW  - Theoretical calculations
Y1  - 2016
U6  - https://doi.org/10.1016/j.tet.2016.03.058
SN  - 0040-4020
VL  - 72
SP  - 2402
EP  - 2410
PB  - Elsevier
CY  - Oxford
ER  - 
TY  - JOUR
A1  - Kleinpeter, Erich
ED  - Webb, GA
T1  - Quantification and visualization of the anisotropy effect in NMR spectroscopy by through-space NMR shieldings
JF  - Annual reports on NMR spectroscopy
JF  - Annual Reports on NMR Spectroscopy
N2  - The anisotropy effect of functional groups (respectively the ring-current effect of aryl moieties) in H-1 NMR spectra has been computed as spatial NICS (through-space NMR chemical shieldings) and visualized by iso-chemical-shielding surfaces of various size and low(high) field direction. Hereby, the anisotropy/ring-current effect, which proves to be the molecular response property of spatial NICS, can be quantified and can be readily employed for assignment purposes in proton NMR spectroscopy-characteristic examples of stereochemistry and position assignments (the latter in supramolecular structures) will be given. In addition, anisotropy/ring-current effects in H-1 NMR spectra can be quantitatively separated from the second dominant structural effect in proton NMR spectra, the steric compression effect, pointing into the reverse direction, and the ring-current effect, by far the strongest anisotropy effect, can be impressively employed to visualize and quantify (anti) aromaticity and to clear up standing physical-organic phenomena as are pseudo-, spherical, captodative, homo-and chelatoaromaticity, to characterize the pi-electronic structure of, for example, fulvenes, fulvalenes, annulenes or fullerenes and to differentiate aromatic and quinonoid structures.
KW  - Through-space NMR shielding (TSNMRS)
KW  - Anisotropy effect
KW  - Stereochemistry
KW  - Ring-current effect
KW  - Aromatic or quinonoid
KW  - Aromaticity
KW  - Chelatoaromaticity
KW  - Binding pocket position
KW  - Supramolecular compounds
KW  - Diastereomers assignment
Y1  - 2014
SN  - 978-0-12-800184-4
U6  - https://doi.org/10.1016/B978-0-12-800184-4.00003-5
SN  - 0066-4103
VL  - 82
SP  - 115
EP  - 166
PB  - Elsevier
CY  - San Diego
ER  -