TY - JOUR AU - Csütörtöki, Renáta AU - Szatmári, István AU - Heydenreich, M AU - Koch, A AU - Starke, I AU - Fülöp, Ferenc AU - Kleinpeter, E TI - Novel piperidine-fused benzoxazino- and quinazolinonaphthoxazines-synthesis and conformational study JF - TETRAHEDRON J2 - TETRAHEDRON VL - 68 PY - 2012 IS - 31 SP - 6284 EP - 6288 PG - 5 SN - 0040-4020 DO - 10.1016/j.tet.2012.05.048 UR - https://m2.mtmt.hu/api/publication/2050038 ID - 2050038 N1 - Megjegyzés-27445337 N1 Funding details: 50368559, DAAD, Deutscher Akademischer Austauschdienst N1 Funding details: OTKA No N1 Funding details: TÁMOP-4.2.1/B-09/KONV-2010-0005 N1 Funding details: K-75433 N1 Funding details: DAAD, Deutscher Akademischer Austauschdienst N1 Funding text: The authors thank the Hungarian Research Foundation (OTKA No. K-75433) and TÁMOP-4.2.1/B-09/KONV-2010-0005 and the Deutsche Akademische Austauschdienst (DAAD), project-ID 50368559, for financial support. I.S. acknowledges the award of a Bolyai János Fellowship. Megjegyzés-27445279 N1 Funding details: 50368559, DAAD, Deutscher Akademischer Austauschdienst N1 Funding details: OTKA No N1 Funding details: TÁMOP-4.2.1/B-09/KONV-2010-0005 N1 Funding details: K-75433 N1 Funding details: DAAD, Deutscher Akademischer Austauschdienst N1 Funding text: The authors thank the Hungarian Research Foundation (OTKA No. K-75433) and TÁMOP-4.2.1/B-09/KONV-2010-0005 and the Deutsche Akademische Austauschdienst (DAAD), project-ID 50368559, for financial support. I.S. acknowledges the award of a Bolyai János Fellowship. WoS:hiba:000306195800025 2019-03-04 19:46 első szerző nem egyezik AB - The reactions of 1-(amino(2-hydroxyphenyl)methyl)-2-naphthol (3) and 1-(amino(2-aminophenyl) methyl)-2-naphthol (6) with glutardialdehyde resulted in the formation of piperidine-fused benzox-azinonaphthoxazine 4 and quinazolinonaphthoxazine 7, respectively, both in diastereopure form. The full conformational search protocols of 4 and 7 were successfully carried out by NMR spectroscopy and accompanying molecular modelling; the global minimum-energy conformers of all diastereomers were computed, and the assignments of the most stable stereoisomers, G(tct)(1) for 4 and G(tct)(1) for 7, were corroborated by spatial NOE information relating to the H-7a-H-10a-H-15b and H,H coupling patterns of the protons in the flexible part of the piperidine moiety. Additionally, mass spectrometric fragmentation was investigated in collision-induced dissociation experiments. The elemental compositions of the ions were determined by accurate mass measurements. (C) 2012 Elsevier Ltd. All rights reserved. LA - English DB - MTMT ER - TY - JOUR AU - Szatmári, István AU - Toth, D AU - Koch, A AU - Heydenreich, M AU - Kleinpeter, E AU - Fülöp, Ferenc TI - Study of the substituent-influenced anomeric effect in the ring-chain tautomerism of 1-alkyl-3-aryl-naphth[1,2-e][1,3]oxazines JF - EUROPEAN JOURNAL OF ORGANIC CHEMISTRY J2 - EUR J ORG CHEM VL - 2006 PY - 2006 IS - 20 SP - 4670 EP - 4675 PG - 6 SN - 1434-193X DO - 10.1002/ejoc.200600563 UR - https://m2.mtmt.hu/api/publication/1078942 ID - 1078942 N1 - Univ Szeged, Inst Pharmaceut Chem, H-6701 Szeged, Hungary. Hungarian Acad Sci, Res Grp Heterocycl Chem, H-6701 Szeged, Hungary. Univ Potsdam, Dept Chem, D-14415 Potsdam, Germany. LA - English DB - MTMT ER - TY - JOUR AU - Toth, D AU - Szatmári, István AU - Fülöp, Ferenc TI - Substituent effects in the ring-chain tautomerism of 1-alkyl-3-arylnaphth[1,2-e][1,3]oxazines JF - EUROPEAN JOURNAL OF ORGANIC CHEMISTRY J2 - EUR J ORG CHEM VL - 2006 PY - 2006 IS - 20 SP - 4664 EP - 4669 PG - 6 SN - 1434-193X DO - 10.1002/ejoc.200600447 UR - https://m2.mtmt.hu/api/publication/1078941 ID - 1078941 N1 - Univ Szeged, Inst Pharmaceut Chem, H-6701 Szeged, Hungary. LA - English DB - MTMT ER - TY - JOUR AU - Szatmári, István AU - Martinek, Tamás AU - Lázár, László AU - Koch, A AU - Kleinpeter, E AU - Neuvonen, K AU - Fülöp, Ferenc TI - Stereoelectronic effects in ring-chain tautomerism of 1,3-diarylnaphth[1,2-e][1,3]oxazines and 3-alkyl-1-arylnaphth[1,2-e][1,3]oxazines JF - JOURNAL OF ORGANIC CHEMISTRY J2 - J ORG CHEM VL - 69 PY - 2004 IS - 11 SP - 3645 EP - 3653 PG - 9 SN - 0022-3263 DO - 10.1021/jo0355810 UR - https://m2.mtmt.hu/api/publication/1013251 ID - 1013251 AB - The disubstitution effects of X and Y in 1-(Y-phenyl)-3-(X- phenyl)-2,3-dihydro-1H-naphth[1,2-e][1,3]oxazines on the ring- chain tautomerism, the delocalization of the nitrogen lone pair (anomeric effect), and the C-13 NMR chemical shifts were analyzed by using multiple linear regression analysis. Study of the three-component equilibrium B reversible arrow A reversible arrow C revealed that the chain reversible arrow trans (A reversible arrow B) equilibrium constants are significantly influenced by the inductive effect (sigma(F)) of substituent Y on the 1-phenyl ring. In contrast, no significant substituent dependence on Y was observed for the chain reversible arrow cis (A reversible arrow C) equilibrium. There was an analogous dependence for the epimerization (C reversible arrow B) constants of 1-(Y-phenyl)-3-alkyl-2,3-dihydro-1H-naphth[1,2-e] [1,3]oxazines. With these model compounds, significant overlapping energies of the nitrogen lone pair was observed by NBO analysis in the trans forms B (to sigma*(C1-C1'), sigma*(C1- C10b), and sigma*(C3-O4)) and in the cis forms C (to sigma*(C1- H), sigma*(C1-C10b), and sigma*(C3-O4)). The effects of disubstitution revealed some characteristic differences between the cis and trans isomers. However, the results do not suggest that the anomeric effect predominates in the preponderance of the trans over the cis isomer. When the C-13 chemical shift changes induced Y by substituents X and Y (SCS) were subjected to multiple linear regression analysis, negative rho(F)(Y) and rho(F)(X) values were observed at C-1 and C-3 for both the cis and trans isomers. In contrast, the positive rho(R)(Y) values at C-1 and the negative rho(R)(X) values at C-3 observed indicated the contribution of resonance structures f (rho(R) > 0) and g (rho(R) < 0), respectively. The classical double bond-no-bond resonance structures proved useful in explaining the substituent sensitivities of the donation energies and the behavior of the SCS values. LA - English DB - MTMT ER - TY - JOUR AU - Szatmári, István AU - Hetényi, Anasztázia AU - Lázár, László AU - Fülöp, Ferenc TI - Transformation reactions of the Betti base analog aminonaphthols JF - JOURNAL OF HETEROCYCLIC CHEMISTRY J2 - J HETEROCYCLIC CHEM VL - 41 PY - 2004 IS - 3 SP - 367 EP - 373 PG - 7 SN - 0022-152X DO - 10.1002/jhet.5570410310 UR - https://m2.mtmt.hu/api/publication/1013250 ID - 1013250 AB - By means of simple or domino ring-closure reactions of 1-(alpha-aminobenzyl)-2-naphthol (Betti base: 1), 1-aminomethyl-2-naplithol (2) and 2-(alpha-aminobenzyl)-1-naphthol (reverse Berri base: 3) with phosgene, ethyl benzimidate, 2-carboxybenzaldehyde, levulinic acid, salicylaldehyde/formalin or salicylaldehyde/acetaldehyde, naphth[1,2-e][1,3]oxazine and naphth[2,1-e][1,3]oxazine derivatives were prepared. All of the nitrogen-bridged polycyclic derivatives of 1 and 3 containing a number of centers of asymmetry were formed with nearly complete diastereoselectivity. Considerable differences were observed in the ring-closing abilities of the unsubstituted and phenyl-substituted aminonaphthols 1 and 2 and of the regioisomeric compounds 1 and 3. LA - English DB - MTMT ER - TY - JOUR AU - Szatmári, István AU - Martinek, Tamás AU - Lázár, László AU - Fülöp, Ferenc TI - Substituent effects in the ring-chain tautomerism of 1,3-diaryl-2,3-dihydro-1H-naphth[1,2-e] [1,3]oxazines JF - TETRAHEDRON J2 - TETRAHEDRON VL - 59 PY - 2003 IS - 16 SP - 2877 EP - 2884 PG - 8 SN - 0040-4020 DO - 10.1016/S0040-4020(03)00331-4 UR - https://m2.mtmt.hu/api/publication/1013529 ID - 1013529 AB - Condensation of Betti base analogue amino naphthols with substituted benzaldehydes led to 1,3-diaryl-2,3-dihydro-1H-naphth[1,2-e][1,3]oxazines (3-9) which proved to be three-component (r(1)-o-r(2)) tautomeric mixtures in CDCl3 at 300 K. The electronic effects of the 3-aryl groups on the ratios of the ring-chain tautomeric forms at equilibrium could be described by the equation log K-X=rhosigma(+)+log K-X=H. The value of the intercept was found to be strongly influenced by the steric arrangement of the 1,3-diaryl substituents. (C) 2003 Elsevier Science Ltd. All rights reserved. LA - English DB - MTMT ER -