Palladium-Catalyzed α-Arylation of Esters: Synthesis of the Tetrahydroisoquinoline Ring

被引：0
作者：
Serban, Georgeta [1 ]
Diaba, Faiza [2 ]
机构：
[1] Univ Oradea, Fac Med & Pharm, Pharmaceut Chem Dept, Nicolae Jiga 29, Oradea 410028, Romania
[2] Univ Barcelona, Lab Quim Organ, Fac Farm, IBUB, Ave Joan XXIII 27-31, Barcelona 08028, Spain
来源：
REACTIONS | 2025年 / 6卷 / 01期
关键词：
tetrahydroisoquinoline; palladium-catalyst; tripotassium phosphate; intramolecular alpha-arylation; carbon-carbon bond formation; NUCLEOPHILIC-SUBSTITUTION; ACID; ALKALOIDS; DERIVATIVES; PROTOCOL; SYSTEM;
D O I：
10.3390/reactions6010017
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
The palladium-catalyzed cross-coupling reaction used for carbon-carbon bond formation is one of the most commonly applied reactions in modern organic synthesis. In this work, a concise strategy was developed for constructing the tetrahydroisoquinoline core, a key structural motif found in many biologically active compounds. This method involves the palladium-catalyzed intramolecular coupling of aryl iodides with ester enolates generated in the presence of K3PO4 as a base, resulting in the formation of the tetrahydroisoquinoline ring with an exceptionally high yield of 84%.
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页数：10
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共 57 条
[1]   Design, synthesis and anti-inflammatory assessment of certain substituted 1,2,4-triazoles bearing tetrahydroisoquinoline scaffold as COX 1/ 2-inhibitors [J].
Abo-Elmagd, Mai, I ;
Hassan, Rasha M. ;
Aboutabl, Mona E. ;
Amin, Kamilia M. ;
El-Azzouny, Aida A. ;
Aboul-Enein, Mohamed N. .
BIOORGANIC CHEMISTRY, 2024, 150
[2]   Muscarinic receptor antagonists for overactive bladder [J].
Abrams, Paul ;
Andersson, Karl-Erik .
BJU INTERNATIONAL, 2007, 100 (05) :987-1006
[3]   First principle study of a potential bioactive molecule with tetrahydroisoquinoline, carbothiomide and adamantane scaffolds [J].
Al-Shehri, Mona M. ;
Al-Majed, Abdul-Rahman A. ;
Aljohar, Haya I. ;
El-Emam, Ali A. ;
Pathak, Shilendra K. ;
Sachan, Alok K. ;
Prasad, Onkar ;
Sinha, Leena .
JOURNAL OF MOLECULAR STRUCTURE, 2017, 1143 :204-216
[4]   In vitro anti-proliferative activity of Argemone gracilenta and identification of some active components [J].
Alberto Leyva-Peralta, Mario ;
Enrique Robles-Zepeda, Ramon ;
Garibay-Escobar, Adriana ;
Ruiz-Bustos, Eduardo ;
Patricia Alvarez-Berber, Laura ;
Carlos Galvez-Ruiz, Juan .
BMC COMPLEMENTARY AND ALTERNATIVE MEDICINE, 2015, 15
[5]  
Amin A., 2022, Open Med. Chem. J, V16, DOI [10.2174/18741045-v16-e2209010, DOI 10.2174/18741045-V16-E2209010]
[6]   A three-component domino protocol for the facile synthesis of highly functionalized tetrahydroisoquinolines by creation of their benzene ring [J].
Balamurugan, Kamaraj ;
Jeyachandran, Veerappan ;
Perumal, Subbu ;
Carlos Menendez, J. .
TETRAHEDRON, 2011, 67 (07) :1432-1437
[7]   Biomedical Application of Orexin/Hypocretin Receptor Ligands in Neuroscience [J].
Boss, Christoph ;
Brisbare-Roch, Catherine ;
Jenck, Francois .
JOURNAL OF MEDICINAL CHEMISTRY, 2009, 52 (04) :891-903
[8]   Cardiac electrophysiologic and antiarrhythmic actions of a pavine alkaloid derivative, O-methyl-neocaryachine, in rat heart [J].
Chang, GJ ;
Su, MJ ;
Hung, TM ;
Lee, SS .
BRITISH JOURNAL OF PHARMACOLOGY, 2002, 136 (03) :459-471
[9]   SYNTHESIS AND PHARMACOLOGICAL CHARACTERIZATION OF 1-PHENYL-1,2,3,4-TETRAHYDROISOQUINOLINE, 4-PHENYL-1,2,3,4-TETRAHYDROISOQUINOLINE, AND 1-BENZYL-1,2,3,4-TETRAHYDROISOQUINOLINE AS DOPAMINE RECEPTOR LIGANDS [J].
CHARIFSON, PS ;
WYRICK, SD ;
HOFFMAN, AJ ;
SIMMONS, RMA ;
BOWEN, JP ;
MCDOUGALD, DL ;
MAILMAN, RB .
JOURNAL OF MEDICINAL CHEMISTRY, 1988, 31 (10) :1941-1946
[10]   Complex Bioactive Alkaloid-Type Polycycles through Efficient Catalytic Asymmetric Multicomponent Aza-Diels-Alder Reaction of Indoles with Oxetane as Directing Group [J].
Chen, Zhilong ;
Wang, Beilei ;
Wang, Zhaobin ;
Zhu, Guangyu ;
Sun, Jianwei .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (07) :2027-2031
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