@article{MTMT:1366571, title = {Convenient Synthesis of 1,2,3,4-Tetrahydroisoquinoline-1-carboxylic Acid Derivatives via Isocyanide-Based, Three-Component Reactions}, url = {https://m2.mtmt.hu/api/publication/1366571}, author = {Schuster, Ildikó and Lázár, László and Fülöp, Ferenc}, doi = {10.1080/00397910903277920}, journal-iso = {SYNTHETIC COMMUN}, journal = {SYNTHETIC COMMUNICATIONS}, volume = {40}, unique-id = {1366571}, issn = {0039-7911}, abstract = {The three-component reactions of 3,4-dihydroisoquinolines, isocyanides, and benzyl chloroformate furnished 2-benzyloxycarbonyl-1,2,3,4-tetrahydroisoquinoline-1-carboxamides in moderate to good yields. Hydrogenolysis or selective hydrolysis of the benzyloxycarbonyl group provided 1,2,3,4-tetrahydroisoquinoline-1-carboxamides, further hydrolysis of which resulted in the corresponding 1,2,3,4-tetrahydroisoquinoline-1-carboxylic acids.}, keywords = {WATER; Isoquinolines; ISOQUINOLINE; TETRAHYDROISOQUINOLINE; MULTICOMPONENT REACTIONS; ISOCYANIDES; ugi reactions; SALTS; STRONG CH-ACIDS; -Amino acids}, year = {2010}, eissn = {1532-2432}, pages = {2488-2498}, orcid-numbers = {Schuster, Ildikó/0000-0001-9997-5729; Lázár, László/0000-0002-2135-8496; Fülöp, Ferenc/0000-0003-1066-5287} } @article{MTMT:1155521, title = {Directed (R)- or (S)-Selective Dynamic Kinetic Enzymatic Hydrolysis of 1,2,3,4-Tetrahydroisoquinoline-1-carboxylic Esters}, url = {https://m2.mtmt.hu/api/publication/1155521}, author = {Paal, TA and Liljeblad, A and Kanerva, LT and Forró, Enikő and Fülöp, Ferenc}, doi = {10.1002/ejoc.200800789}, journal-iso = {EUR J ORG CHEM}, journal = {EUROPEAN JOURNAL OF ORGANIC CHEMISTRY}, volume = {2008}, unique-id = {1155521}, issn = {1434-193X}, abstract = {The first synthesis of both enantiomers of 6,7-dimethoxy-1,2,3,4-tetrahydroisoquinotine-1-carboxylic acid was accomplished through dynamic kinetic resolution in procedures based on CAL-B- or subtilisin Carlsberg-catalysed enantioselective hydrolysis of the corresponding ethyl esters in aqueous NH4OAc buffer at pH 8.5. The products were obtained with high enantiopurity (92-93%ee) in good yields (85-92%). (R)-1,2,3,4-Tetrahydroisoquinotine-1-carboxylic acid was obtained with high enantiopurity (98%ee) and in good yield (85 %) in a CAL-B-catalysed process, under similar conditions. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)}, year = {2008}, eissn = {1099-0690}, pages = {5269-5276}, orcid-numbers = {Forró, Enikő/0000-0001-6796-3889; Fülöp, Ferenc/0000-0003-1066-5287} } @article{MTMT:1084514, title = {Lipase-catalyzed Kinetic And Dynamic Kinetic Resolution of 1,2,3,4-tetrahydroisoquinoline-1-carboxylic Acid}, url = {https://m2.mtmt.hu/api/publication/1084514}, author = {Paal, TA and Forró, Enikő and Liljeblad, A and Kanerva, LT and Fülöp, Ferenc}, doi = {10.1016/j.tetasy.2007.05.016}, journal-iso = {TETRAHEDRON ASYMMETR}, journal = {TETRAHEDRON-ASYMMETRY}, volume = {18}, unique-id = {1084514}, issn = {0957-4166}, abstract = {A dynamic kinetic resolution method for the preparation of enantiopure 1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid (R)-2 was developed involving the CAL-B-catalyzed enantioselective hydrolysis of the corresponding ethyl ester (+/-)-1 in toluene/acetonitrile (4: 1) containing 1 equiv of added water and 0.25 equiv of dipropylamine. This method allowed the preparation of (R)-2 (ee = 96%) with 80% isolated yield. The kinetic resolution of (+/-)-1 in diisopropyl ether at 3 degrees C afforded both enantiomers with ee >= 92%. (c) 2007 Elsevier Ltd. All rights reserved.}, year = {2007}, eissn = {1362-511X}, pages = {1428-1433}, orcid-numbers = {Forró, Enikő/0000-0001-6796-3889; Fülöp, Ferenc/0000-0003-1066-5287} } @article{MTMT:1083281, title = {Synthesis of 1,2,3,4-tetrahydroisoquinoline-1-carboxylic Acid Derivatives Via Ugi Reactions}, url = {https://m2.mtmt.hu/api/publication/1083281}, author = {Schuster, Ildikó and Sztojkov-Ivanov, Anita and Lázár, László and Fülöp, Ferenc}, doi = {10.2174/157017807780414226}, journal-iso = {LETT ORG CHEM}, journal = {LETTERS IN ORGANIC CHEMISTRY}, volume = {4}, unique-id = {1083281}, issn = {1570-1786}, abstract = {The three-component Ugi reactions of 3,4-dihydroisoquinolines, isocyanides and acids furnished 2-acyl-N-substituted-1,2,3,4-tetrahydroisoquinoline-1-carboxamides in moderate to good yields. Chiral, nonracemic acids induced only poor diastercoselectivities in the condensations. Hydrolysis of the Ugi carboxamides gave the corresponding 1,2,3,4-tetrahydroisoquinoline-1-carboxylic acids, which due to their ready ability to undergo racemization, were obtained as racemic mixtures or with low enantiomeric excesses.}, year = {2007}, eissn = {1875-6255}, pages = {102-108}, orcid-numbers = {Schuster, Ildikó/0000-0001-9997-5729; Lázár, László/0000-0002-2135-8496; Fülöp, Ferenc/0000-0003-1066-5287} } @article{MTMT:1012939, title = {Synthesis and conformational analysis of tetrahydroisoquinoline and piperidine-fused 1,3,4,2-oxadiazaphosphinanes, new ring systems}, url = {https://m2.mtmt.hu/api/publication/1012939}, author = {Zalán, Zita and Martinek, Tamás and Lázár, László and Sillanpaa, R and Fülöp, Ferenc}, doi = {10.1016/j.tet.2006.01.018}, journal-iso = {TETRAHEDRON}, journal = {TETRAHEDRON}, volume = {62}, unique-id = {1012939}, issn = {0040-4020}, abstract = {Through cyclization of tetrahydroisoquinoline and piperidine 1,2-hydrazino alcohols with phenylphosphonic dichloride and phenyl dichlorophosphate, P-epimeric diastereomers of 1,6,7,11b-tetrahydro-4H-1,3,4,2-oxidiazaphosphino[5,4-a]isoquinoline-3-o xides (13 and 14). 1,6,11,11a-tetrahydro-4H-1,3,4,2-oxadiazaphosphino[4,5-b]isoquinoline-3- oxides (15 and 16) and 1,6,7,8,9,9a-hexahydro-4H-pyrido[1,2-d][1,3,4,2]oxadiazaphosphinane-3-ox ides (17 and 18), the first representatives of these ring systems, were prepared. NMR and X-ray diffraction studies revealed that, independently of the P-substituent and the relative configuration of the phosphorus atom, 13, 14, 17 and 18 could be characterized by trans-connected hetero rings and the chair conformation of the 1,3,4,2-oxadiazaphosphinane moiety, while the stereochemistry of the connection of the hetero rings in the 1,3,4,2-oxidiazaphosphinanes linearly fused to tetrahydroisoquinoline (15 and 16) was found to be dependent on the P-configuration relative to that of the carbon at the annelation. (c) 2006 Elsevier Ltd. All rights reserved.}, year = {2006}, eissn = {1464-5416}, pages = {2883-2891}, 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} }