TY - JOUR AU - Schuster, Ildikó AU - Lázár, László AU - Fülöp, Ferenc TI - Convenient Synthesis of 1,2,3,4-Tetrahydroisoquinoline-1-carboxylic Acid Derivatives via Isocyanide-Based, Three-Component Reactions JF - SYNTHETIC COMMUNICATIONS J2 - SYNTHETIC COMMUN VL - 40 PY - 2010 IS - 16 SP - 2488 EP - 2498 PG - 11 SN - 0039-7911 DO - 10.1080/00397910903277920 UR - https://m2.mtmt.hu/api/publication/1366571 ID - 1366571 N1 - Megjegyzés-21039019 FU: Hungarian Scientific Research Foundation [OTKA K 075433] FX: The authors thank the Hungarian Scientific Research Foundation (Grant : No. OTKA K 075433) for financial support. WoS:hiba:000280389500017 2019-03-02 08:50 cikkazonosító nem egyezik AB - 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. LA - English DB - MTMT ER - TY - JOUR AU - Paal, TA AU - Liljeblad, A AU - Kanerva, LT AU - Forró, Enikő AU - Fülöp, Ferenc TI - Directed (R)- or (S)-Selective Dynamic Kinetic Enzymatic Hydrolysis of 1,2,3,4-Tetrahydroisoquinoline-1-carboxylic Esters JF - EUROPEAN JOURNAL OF ORGANIC CHEMISTRY J2 - EUR J ORG CHEM VL - 2008 PY - 2008 IS - 31 SP - 5269 EP - 5276 PG - 8 SN - 1434-193X DO - 10.1002/ejoc.200800789 UR - https://m2.mtmt.hu/api/publication/1155521 ID - 1155521 AB - 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) LA - English DB - MTMT ER - TY - JOUR AU - Paal, TA AU - Forró, Enikő AU - Liljeblad, A AU - Kanerva, LT AU - Fülöp, Ferenc TI - Lipase-catalyzed Kinetic And Dynamic Kinetic Resolution of 1,2,3,4-tetrahydroisoquinoline-1-carboxylic Acid JF - TETRAHEDRON-ASYMMETRY J2 - TETRAHEDRON ASYMMETR VL - 18 PY - 2007 IS - 12 SP - 1428 EP - 1433 PG - 6 SN - 0957-4166 DO - 10.1016/j.tetasy.2007.05.016 UR - https://m2.mtmt.hu/api/publication/1084514 ID - 1084514 N1 - Univ Szeged, Inst Pharmaceut Chem, H-6720 Szeged, Hungary. Univ Turku, Lab Synthet Drug Chem, Dept Pharmacol, FIN-20250 Turku, Finland. Megjegyzés-10257365 [271789] AB - 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. LA - English DB - MTMT ER - TY - JOUR AU - Schuster, Ildikó AU - Sztojkov-Ivanov, Anita AU - Lázár, László AU - Fülöp, Ferenc TI - Synthesis of 1,2,3,4-tetrahydroisoquinoline-1-carboxylic Acid Derivatives Via Ugi Reactions JF - LETTERS IN ORGANIC CHEMISTRY J2 - LETT ORG CHEM VL - 4 PY - 2007 IS - 2 SP - 102 EP - 108 PG - 7 SN - 1570-1786 DO - 10.2174/157017807780414226 UR - https://m2.mtmt.hu/api/publication/1083281 ID - 1083281 N1 - Univ Szeged, Inst Pharmaceut Chem, H-6701 Szeged, Hungary. AB - 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. LA - English DB - MTMT ER - TY - JOUR AU - Zalán, Zita AU - Martinek, Tamás AU - Lázár, László AU - Sillanpaa, R AU - Fülöp, Ferenc TI - Synthesis and conformational analysis of tetrahydroisoquinoline and piperidine-fused 1,3,4,2-oxadiazaphosphinanes, new ring systems JF - TETRAHEDRON J2 - TETRAHEDRON VL - 62 PY - 2006 IS - 12 SP - 2883 EP - 2891 PG - 9 SN - 0040-4020 DO - 10.1016/j.tet.2006.01.018 UR - https://m2.mtmt.hu/api/publication/1012939 ID - 1012939 N1 - Institute of Pharmaceutical Chemistry, University of Szeged, PO Box 121, H-6701 Szeged, Hungary Department of Chemistry, University of Jyväskylä, PO Box 35, 40351 Jyväskylä, Finland Cited By :27 Export Date: 15 February 2023 CODEN: TETRA Correspondence Address: Fülöp, F.; Institute of Pharmaceutical Chemistry, PO Box 121, H-6701 Szeged, Hungary; email: fulop@pharm.u-szeged.hu Funding details: Hungarian Scientific Research Fund, OTKA, T049407 Funding text 1: The authors' thanks are due to the Hungarian Research Foundation (OTKA No. T049407) for financial support. AB - 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. LA - English DB - MTMT ER -