TY  - JOUR
AU  - Hetényi, Anasztázia
AU  - Szakonyi, Zsolt
AU  - Klika, K D
AU  - Pihlaja, K
AU  - Fülöp, Ferenc
TI  - Formation and characterization of a multicomponent equilibrium system derived from cis- and trans-1-aminomethylcyclohexane-1,2-diol
JF  - JOURNAL OF ORGANIC CHEMISTRY
J2  - J ORG CHEM
VL  - 68
PY  - 2003
IS  - 6
SP  - 2175
EP  - 2182
PG  - 8
SN  - 0022-3263
DO  - 10.1021/jo026428t
UR  - https://m2.mtmt.hu/api/publication/1013533
ID  - 1013533
N1  - CAplus AN 2003:127465; MEDLINE PMID: 12636377 (Journal; Article);
AB  - Both cis and trans isomers of amino diols 3-6 were prepared stereoselectively. In the reactions between 3-6 and phenyl isothiocyanate, the ring closure proceeded regioselectively and resulted only in spiro derivatives of 2-phenyliminooxazolidines 9, 10, 13, and 14. The reaction of cis- (or trans-)1-aminomethylcyclohexane-1,2-diol 4 (or 6) with 1 equiv of an aromatic aldehyde 15a-g in EtOH at room temperature resulted in a complex, multicomponent equilibrium mixture of 16a-g and 18a-g (or 17a-g and 19a-g), in each case consisting of a five-component, ring-chain tautomeric system 16A-E (or 17A-E), involving the Schiff base, two epimeric spirooxazolidines, two epimeric condensed 1,3-oxazines, and some of the four tricyclic compounds 18A-D (or 19A-D). The five-component, ring-chain equilibria were found to be adequately described by the Hammett-Brown linear free energy equation.
LA  - English
DB  - MTMT
ER  - 

TY  - JOUR
AU  - Lázár, László
AU  - Fülöp, Ferenc
TI  - Recent developments in the ring-chain tautomerism of 1,3-heterocycles
JF  - EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
J2  - EUR J ORG CHEM
VL  - 2003
PY  - 2003
IS  - 16
SP  - 3025
EP  - 3042
PG  - 18
SN  - 1434-193X
DO  - 10.1002/ejoc.200300142
UR  - https://m2.mtmt.hu/api/publication/1013522
ID  - 1013522
N1  - Cited By :119            
            Export Date: 15 May 2023            
            CODEN: EJOCF            
            Correspondence Address: Fülöp, F.; Inst. of Pharmaceutical Chemistry, POB 121, 6701 Szeged, Hungary; email: fulop@pharma.szote.u-szeged.hu
LA  - English
DB  - MTMT
ER  - 

TY  - JOUR
AU  - Göblyös, Anikó
AU  - Lázár, László
AU  - Fülöp, Ferenc
TI  - Ring-chain tautomerism of 2-aryl-substituted-hexahydropyrimidines and tetrahydroquinazolines
JF  - TETRAHEDRON
J2  - TETRAHEDRON
VL  - 58
PY  - 2002
SP  - 1011
EP  - 1016
PG  - 6
SN  - 0040-4020
DO  - 10.1016/S0040-4020(01)01196-6
UR  - https://m2.mtmt.hu/api/publication/1013828
ID  - 1013828
N1  - Cited By :42            
            Export Date: 15 May 2023            
            Funding details: Hungarian Scientific Research Fund, OTKA, T034452, T034901            
            Funding text 1: We are grateful to Dr Tamás Martinek for helpful discussions concerning the NMR assignments and to the Hungarian Research Foundation (OTKA No. T034901, T034452) for financial support.
AB  - 2-Aryl-substituted-1-isopropyl- and 1-phenylhexahydropyrimidines and 3-isopropyl- and 3-phenyl-1,2,3,4-tetrahydroquinazolines proved to be ring-chain tautomeric mixtures in CDCl3 at 300 K, whereas only ring-closed tautomers could be detected for the 1- or 3-methyl-substituted analogues. The ratios of the ring-chain tautomeric forms at equilibrium could be described by the equation log K-x rhosigma(+) + log K-X=H. (C) 2002 Elsevier Science Ltd. All rights reserved.
LA  - English
DB  - MTMT
ER  -