@article{MTMT:2050038, title = {Novel piperidine-fused benzoxazino- and quinazolinonaphthoxazines-synthesis and conformational study}, url = {https://m2.mtmt.hu/api/publication/2050038}, author = {Csütörtöki, Renáta and Szatmári, István and Heydenreich, M and Koch, A and Starke, I and Fülöp, Ferenc and Kleinpeter, E}, doi = {10.1016/j.tet.2012.05.048}, journal-iso = {TETRAHEDRON}, journal = {TETRAHEDRON}, volume = {68}, unique-id = {2050038}, issn = {0040-4020}, abstract = {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.}, keywords = {DERIVATIVES; DENSITY; PARAMETERS; SATURATED HETEROCYCLES; Optimization; Quinazolines; conformational analysis; SEMIEMPIRICAL METHODS; IONIZATION MASS-SPECTRA; naphthoxazines; NMR-SPECTRA; NMR spectroscopy; DFT structural study}, year = {2012}, eissn = {1464-5416}, pages = {6284-6288}, orcid-numbers = {Szatmári, István/0000-0002-8571-5229; Fülöp, Ferenc/0000-0003-1066-5287} } @article{MTMT:1078942, title = {Study of the substituent-influenced anomeric effect in the ring-chain tautomerism of 1-alkyl-3-aryl-naphth[1,2-e][1,3]oxazines}, url = {https://m2.mtmt.hu/api/publication/1078942}, author = {Szatmári, István and Toth, D and Koch, A and Heydenreich, M and Kleinpeter, E and Fülöp, Ferenc}, doi = {10.1002/ejoc.200600563}, journal-iso = {EUR J ORG CHEM}, journal = {EUROPEAN JOURNAL OF ORGANIC CHEMISTRY}, volume = {2006}, unique-id = {1078942}, issn = {1434-193X}, year = {2006}, eissn = {1099-0690}, pages = {4670-4675}, orcid-numbers = {Szatmári, István/0000-0002-8571-5229; Fülöp, Ferenc/0000-0003-1066-5287} } @article{MTMT:1078941, title = {Substituent effects in the ring-chain tautomerism of 1-alkyl-3-arylnaphth[1,2-e][1,3]oxazines}, url = {https://m2.mtmt.hu/api/publication/1078941}, author = {Toth, D and Szatmári, István and Fülöp, Ferenc}, doi = {10.1002/ejoc.200600447}, journal-iso = {EUR J ORG CHEM}, journal = {EUROPEAN JOURNAL OF ORGANIC CHEMISTRY}, volume = {2006}, unique-id = {1078941}, issn = {1434-193X}, year = {2006}, eissn = {1099-0690}, pages = {4664-4669}, orcid-numbers = {Szatmári, István/0000-0002-8571-5229; Fülöp, Ferenc/0000-0003-1066-5287} } @article{MTMT:1013251, title = {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}, url = {https://m2.mtmt.hu/api/publication/1013251}, author = {Szatmári, István and Martinek, Tamás and Lázár, László and Koch, A and Kleinpeter, E and Neuvonen, K and Fülöp, Ferenc}, doi = {10.1021/jo0355810}, journal-iso = {J ORG CHEM}, journal = {JOURNAL OF ORGANIC CHEMISTRY}, volume = {69}, unique-id = {1013251}, issn = {0022-3263}, abstract = {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.}, year = {2004}, eissn = {1520-6904}, pages = {3645-3653}, orcid-numbers = {Szatmári, István/0000-0002-8571-5229; Martinek, Tamás/0000-0003-3168-8066; Lázár, László/0000-0002-2135-8496; Fülöp, Ferenc/0000-0003-1066-5287} } @article{MTMT:1013250, title = {Transformation reactions of the Betti base analog aminonaphthols}, url = {https://m2.mtmt.hu/api/publication/1013250}, author = {Szatmári, István and Hetényi, Anasztázia and Lázár, László and Fülöp, Ferenc}, doi = {10.1002/jhet.5570410310}, journal-iso = {J HETEROCYCLIC CHEM}, journal = {JOURNAL OF HETEROCYCLIC CHEMISTRY}, volume = {41}, unique-id = {1013250}, issn = {0022-152X}, abstract = {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.}, year = {2004}, eissn = {1943-5193}, pages = {367-373}, orcid-numbers = {Szatmári, István/0000-0002-8571-5229; Hetényi, Anasztázia/0000-0001-8080-6992; Lázár, László/0000-0002-2135-8496; Fülöp, Ferenc/0000-0003-1066-5287} } @article{MTMT:1013529, title = {Substituent effects in the ring-chain tautomerism of 1,3-diaryl-2,3-dihydro-1H-naphth[1,2-e] [1,3]oxazines}, url = {https://m2.mtmt.hu/api/publication/1013529}, author = {Szatmári, István and Martinek, Tamás and Lázár, László and Fülöp, Ferenc}, doi = {10.1016/S0040-4020(03)00331-4}, journal-iso = {TETRAHEDRON}, journal = {TETRAHEDRON}, volume = {59}, unique-id = {1013529}, issn = {0040-4020}, abstract = {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.}, year = {2003}, eissn = {1464-5416}, pages = {2877-2884}, orcid-numbers = {Szatmári, István/0000-0002-8571-5229; Martinek, Tamás/0000-0003-3168-8066; Lázár, László/0000-0002-2135-8496; Fülöp, Ferenc/0000-0003-1066-5287} }