TY  - JOUR
AU  - Schuster, Ildikó
AU  - Koch, A
AU  - Heydenreich, M
AU  - Kleinpeter, E
AU  - Forró, Enikő
AU  - Lázár, László
AU  - Sillanpaa, R
AU  - Fülöp, Ferenc
TI  - Synthesis and conformational analysis of tetrahydroisoquinoline-fused 1,3,2-oxazaphospholidines and 1,2,3-oxathiazolidines
JF  - EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
J2  - EUR J ORG CHEM
VL  - 2008
PY  - 2008
IS  - 8
SP  - 1464
EP  - 1472
PG  - 9
SN  - 1434-193X
DO  - 10.1002/ejoc.200701026
UR  - https://m2.mtmt.hu/api/publication/1124327
ID  - 1124327
N1  - Institute of Pharmaceutical Chemistry, University of Szeged, Eötvös u. 6, 6720 Szeged, Hungary            
            Department of Chemistry, University of Potsdam, P. O. Box 691553, 14415 Potsdam, Germany            
            Department of Chemistry, University of Jyväskylä, P. O. Box 35, 40351 Jyväskylä, Finland            
            Cited By :11            
            Export Date: 22 February 2023            
            CODEN: EJOCF            
            Correspondence Address: Kleinpeter, E.; Department of Chemistry, P. O. Box 691553, 14415 Potsdam, Germany; email: kp@chem.uni-potsdam.de
AB  - The cyclizations of tetrahydroisoquinoline 1,2-amino alcohols with
phenylphosphonic dichloride, bis(2-chloroethyl)phosphoramidic
dichloride, thionyl chloride and sulfuryl chloride were utilized to
synthesize
1,5,6,10b-tetrahydro-1,3,2-oxazaphospholo[4,3-a]isoquinolines (2, 3),
1,5,10,10a-tetrahydro-1,3,2-oxazaphospholo[3,4-b]isoquinolines (8, 9),
1,5,6,10b-tetrahydro-1,2,3-oxathiazolo[4,3-a]isoquinolines (4-6) and a
1,5,10,10a-tetrahydro-1,2,3-oxathiazolo[3,4-b]isoquinoline (11), which
are the first representatives of these ring systems. NMR spectroscopic
analysis revealed the existence of conformational equilibria that are
fast on the NMR timescale. Theoretical DFT calculations pointed to the
participation of generally two preferred conformers in the
conformational equilibria; the positions of the equilibria were
indicated by the experimental NMR spectroscopic parameters, and they
are in good agreement with the theoretically calculated energy
differences of the participating conformers. For two compounds, which
could be not isolated (10, 12), both the preferred conformers and the
stereochemistry could be concluded from the DFT calculation results.
((c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008).
LA  - English
DB  - MTMT
ER  -