@article{BelasriTopalHeydenreichetal.2020, author = {Belasri, Khadija and Topal, Leila and Heydenreich, Matthias and Koch, Andreas and Kleinpeter, Erich and Fulop, Ferenc and Szatmari, Istvan}, title = {Synthesis and conformational analysis of naphthoxazine-fused phenanthrene derivatives}, series = {Molecules}, volume = {25}, journal = {Molecules}, number = {11}, publisher = {MDPI}, address = {Basel}, issn = {1420-3049}, doi = {10.3390/molecules25112524}, pages = {15}, year = {2020}, abstract = {The synthesis of new phenanthr[9,10-e][1,3]oxazines was achieved by the direct coupling of 9-phenanthrol with cyclic imines in the modified aza-Friedel-Crafts reaction followed by the ring closure of the resulting bifunctional aminophenanthrols with formaldehyde. Aminophenanthrol-type Mannich bases were synthesised and transformed to phenanthr[9,10-e][1,3]oxazines via [4 + 2] cycloaddition. Detailed NMR structural analyses of the new polyheterocycles as well as conformational studies including Density Functional Theory (DFT) modelling were performed. The relative stability of ortho-quinone methides (o-QMs) was calculated, the geometries obtained were compared with the experimentally determined NMR structures, and thereby, the regioselectivity of the reactions has been assigned.}, language = {en} } @article{CsuetoertoekiSzatmariKochetal.2011, author = {Csuetoertoeki, Renata and Szatmari, Istvan and Koch, Andreas and Heydenreich, Matthias and Kleinpeter, Erich and Fueloep, Ferenc}, title = {Synthesis and conformational analysis of new naphth[1,2-e][1,3]oxazino[3,4-c]quinazoline derivatives}, series = {Tetrahedron}, volume = {67}, journal = {Tetrahedron}, number = {44}, publisher = {Elsevier}, address = {Oxford}, issn = {0040-4020}, doi = {10.1016/j.tet.2011.08.074}, pages = {8564 -- 8571}, year = {2011}, abstract = {A new highly functionalized aminonaphthol derivative, 1-(amino(2-aminophenyl)methyl)-2-naphthol (4), was synthesized by the reaction of 2-naphthol, 2-nitrobenzaldehyde and tert-butyl carbamate or benzyl carbamate, followed by reduction and/or removal of the protecting group. The aminonaphthol derivative thus obtained was converted in ring-closure reactions with formaldehyde. benzaldehyde and/or phosgene to the corresponding naphth[1,2-e][1,3]oxazino[3,4-c]quinazoline derivatives. The conformational analysis of some derivatives by NMR spectroscopy and accompanying molecular modelling are also reported.}, language = {en} }