@article{MTMT:1013243, title = {A convenient and highly stereoselective synthesis of 14-substituted 8,13-diazaoestrone analogues by domino ring closures}, url = {https://m2.mtmt.hu/api/publication/1013243}, author = {Lázár, László and Kivela, H and Pihlaja, K and Fülöp, Ferenc}, doi = {10.1016/j.tetlet.2004.05.054}, journal-iso = {TETRAHEDRON LETT}, journal = {TETRAHEDRON LETTERS}, volume = {45}, unique-id = {1013243}, issn = {0040-4039}, abstract = {By means of convenient domino ring closure reactions of 1-(2-aminoethyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline 2 and 7-oxo-acids, 14-substituted 8,13-diazaoestrone derivatives (5 and 6) were formed with similar to100% diastereoselectivity. (C) 2004 Elsevier Ltd. All rights reserved.}, year = {2004}, eissn = {1873-3581}, pages = {6199-6201}, orcid-numbers = {Lázár, László/0000-0002-2135-8496; Fülöp, Ferenc/0000-0003-1066-5287} } @article{MTMT:1013527, title = {Substituent-dependent negative hyperconjugation in 2-aryl-1,3-N,N-heterocycles. Fine-tuned anomeric effect?}, url = {https://m2.mtmt.hu/api/publication/1013527}, author = {Hetényi, Anasztázia and Martinek, Tamás and Lázár, László and Zalán, Zita and Fülöp, Ferenc}, doi = {10.1021/jo034417}, journal-iso = {J ORG CHEM}, journal = {JOURNAL OF ORGANIC CHEMISTRY}, volume = {68}, unique-id = {1013527}, issn = {0022-3263}, abstract = {The epimerization reactions of conformationally inflexible 2-aryl-1,3-N,N-heterocycles were used as model systems to study the role of the nitrogen lone pair-C2 associated antibonding orbital hyperconjugative interactions in the experimentally observed substituent-dependent generalized anomeric effect. The measured reaction free enthalpies were found to correlate well with the sum of the hyperconjugative stabilization energies of all the vicinal donor-acceptor orbital overlaps around C2, obtained from ab initio NBO analysis, and both quantities correlated linearly with the Hammett-Brown substituent constant. The individual stereoelectronic interactions (n(N)-sigma*(C2-N), n(N)-sigma*(C2-Ar), n(N-sigma)*(C2-H)) were also observed to exhibit a substituent dependence, despite their distance from the 2-aryl substituent and their nonperiplanar arrangement. The higher the electron-withdrawing effect of the 2-aryl substituent, the larger was the stabilization for n(N)-sigma*(C2-Ar), while the overlaps n(N)-sigma*(C2-N) and n(N)-sigma*(C2-H) changed in the opposite sense. The different polarization of the acceptor sigma* orbitals, caused by the 2-aryl substituent, accounted for the observed propagation of the substituent effect. These results promote a detailed explanation of the useful tautomeric behavior of the 2-aryl-1,3-X,N-heterocycles, and reveal the nature of the connection between the anomeric effect and the Hammett-type linear free energy relationship.}, year = {2003}, eissn = {1520-6904}, pages = {5705-5712}, orcid-numbers = {Hetényi, Anasztázia/0000-0001-8080-6992; Martinek, Tamás/0000-0003-3168-8066; Lázár, László/0000-0002-2135-8496; Zalán, Zita/0000-0002-7146-3024; Fülöp, Ferenc/0000-0003-1066-5287} } @article{MTMT:1013518, title = {Synthesis and conformational analysis of 1,3,2-diazaphosphorino[6,1-a]isoquinolines, a new ring system}, url = {https://m2.mtmt.hu/api/publication/1013518}, author = {Zalán, Zita and Martinek, Tamás and Lázár, László and Fülöp, Ferenc}, doi = {10.1016/j.tet.2003.09.062}, journal-iso = {TETRAHEDRON}, journal = {TETRAHEDRON}, volume = {59}, unique-id = {1013518}, issn = {0040-4020}, abstract = {Through ring-closure reactions of N- or V-substituted 1-(2'-aminoethyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolines (5a-e) with phenylphosphonyl dichloride, 1- or 3-substituted 4-phenyl-1,3,4,6,7,11b-tetrahydro-2H-1,3,2-diazaphosphorino[6,1-a]isoqui nolin-4-one diastereomers (7a-e and 8a-c,e), the first representatives of a new ring system, were prepared. The diastereomeric ratios in the cyclizations and the conformer (A-E) populations of the nitrogen-bridged tricyclic systems (7 and 8) were strongly influenced by the N- and 1'-substituents of the starting diamines. The conformational analysis of compounds 7 and 8 was performed by H-1, C-13 and P-31 NMR methods. (C) 2003 Elsevier Ltd. All rights reserved.}, year = {2003}, eissn = {1464-5416}, pages = {9117-9125}, orcid-numbers = {Zalán, Zita/0000-0002-7146-3024; Martinek, Tamás/0000-0003-3168-8066; Lázár, László/0000-0002-2135-8496; Fülöp, Ferenc/0000-0003-1066-5287} }