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Journal articles on the topic 'Tetrahydroisoquinolines'

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Published: 4 June 2021

Last updated: 20 July 2024

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1

Ponzo, Viviana L., and Teodoro S. Kaufman. "Synthesis of 3-substituted tetrahydroisoquinolines by acid-catalyzed cyclization of p-toluenesulfonamides of N-benzyl aminoacetaldehyde derivatives." Canadian Journal of Chemistry 73, no. 8 (August 1, 1995): 1348–56. http://dx.doi.org/10.1139/v95-166.

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The acid-catalyzed cyclization of p-toluenesulfonamides of N-benzyl aminoacetaldehyde, or their acetalic counterparts, usually yields 1,2-dihydroisoquinolines. However, cyclization of intermediates bearing a substituent α to the carbonyl group affords 3-substituted 2-p-toluenesulfonyl tetrahydroisoquinolin-4-ol derivatives, capable of further transformation into the related 1,2,3,4-tetrahydroisoquinolines. Keywords: 3-substituted tetrahydroisoquinolines, MY336-a analog, acid-catalyzed cyclization, tetrahydroisoquinolin-4-ol derivatives.

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2

Kmieciak, Anna, Marta Ćwiklińska, Karolina Jeżak, Afef Shili, and Marek P. Krzemiński. "Searching for New Biologically Active Compounds Derived from Isoquinoline Alkaloids." Chemistry Proceedings 3, no. 1 (November 14, 2020): 97. http://dx.doi.org/10.3390/ecsoc-24-08417.

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Many isoquinoline alkaloids are biologically active compounds and successfully used as pharmaceuticals. Compounds belonging to the isoquinolines and tetrahydroisoquinolines (TIQs) can be used as anesthetics, antihypertensive drugs, antiviral agents, and vasodilators. In the presented studies, the search for new compounds and synthesis of tetrahydroisoquinoline alkaloid derivatives was undertaken. Several dihydroisoquinolines were synthesized by Bishler–Napieralski reaction from the corresponding amides. Dihydroisoquinolines were reduced with sodium borohydride to obtain racemic tetrahydroisoquinolines. Asymmetric reduction of selected 3,4-dihydroisoquinolines was attempted with borane in the presence of chiral terpene spiroboranes.

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3

Forni, José Augusto, Martin Brzozowski, John Tsanaktsidis, G. Paul Savage, and Anastasios Polyzos. "Rapid Microwave-Assisted Synthesis of N-Aryl 1,2,3,4-Tetrahydroisoquinolines." Australian Journal of Chemistry 68, no. 12 (2015): 1890. http://dx.doi.org/10.1071/ch15490.

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N-aryl 1,2,3,4-tetrahydroisoquinolines were prepared rapidly in good yields by the microwave-assisted Pd-catalysed coupling of (hetero)aryl iodides or bromides with 1,2,3,4-tetrahydroisoquinoline. Reactions were typically complete within 5 min for aryl iodides and within 30 min for pyridyl bromides.

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4

Ding, Ming-Wu, Long Zhao, Mao-Lin Yang, and Mei Sun. "One-Pot Synthesis of 3-(1,2,3,4-Tetrahydroisoquinolin-1-yl)-isoquinolin-1(2H)-ones by DEAD-Promoted Oxidative Ugi–Wittig Reaction Starting from Phosphonium Salt Precursors." Synlett 33, no. 01 (October 4, 2021): 66–69. http://dx.doi.org/10.1055/a-1661-3378.

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AbstractA new one-pot synthesis of 3-(1,2,3,4-tetrahydroisoquinolin-1-yl)-isoquinolin-1(2H)-ones by DEAD-promoted oxidative Ugi–Wittig reaction was developed. The sequential reactions of (2-carboxybenzyl)triphenylphosphonium salts, isocyanides, and N-aryl-1,2,3,4-tetrahydroisoquinolines produced 3-(1,2,3,4-tetrahydroisoquinolin-1-yl)-isoquinolin-1(2H)-ones in moderate to good overall yields in the presence of DEAD and Et3N.

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5

Azamatov, Azizbek A., Sherzod N. Zhurakulov, Valentina I. Vinogradova, Firuza Tursunkhodzhaeva, Roaa M. Khinkar, Rania T. Malatani, Mohammed M. Aldurdunji, Antonio Tiezzi, and Nilufar Z. Mamadalieva. "Evaluation of the Local Anesthetic Activity, Acute Toxicity, and Structure–Toxicity Relationship in Series of Synthesized 1-Aryltetrahydroisoquinoline Alkaloid Derivatives In Vivo and In Silico." Molecules 28, no. 2 (January 4, 2023): 477. http://dx.doi.org/10.3390/molecules28020477.

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Isoquinoline alkaloids constitute one of the most common classes of alkaloids that have shown a pronounced role in curing various diseases. Finding ways to reduce the toxicity of these molecules and to increase their therapeutic margin is an urgent matter. Here, a one-step method for the synthesis of a series of 1-aryl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolines was performed in 85–98% yield by the Pictet–Spengler reaction. This was accomplished using the reaction between 3,4-dimethoxyphenylethylamine and substituted benzaldehydes boiling in trifluoroacetic acid. Furthermore, 1-(3′-amino-, 4′-aminophenyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolines were obtained in 94% and 97% yield by reduction in 1-(3′-nitro-, 4′-nitrophenyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolines with SnCl2 × 2H2O. The structures of the substances obtained were confirmed by infrared (IR) and nuclear magnetic resonance (1H and 13C NMR) spectra. ADMET/TOPKAT in silico study concluded that the synthesized compounds exhibited acceptable pharmacodynamic and pharmacokinetic properties without carcinogenic or mutagenic potential but with variable hepatotoxicity. The acute toxicity and structure–toxicity relationship (STR) in the series of 20 derivatives of 1-aryl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolines (3a-r, 4a, b) was studied via determination of acute toxicity and resorptive action in white mice employing intragastric step-by-step administration. The first compound, 1-phenyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride (3a), showed the highest toxicity with LD50 of 280 mg/kg in contrast to 1-(3′-bromo -4′-hydroxyphenyl)-6,7-methylenedioxy-1,2,3,4-tetrahydroisoquinoline hydrochloride (3e) which proved to be the safest of the compounds studied. Its toxicity was 13.75 times lower than that of the parent compound 3a. All compounds investigated showed high local anesthetic activity on rabbit eyes in the concentrations studied. Only 3r, 3n, and 4a caused eye irritation and redness. All investigated derivatives (except 4b) in 1% concentration were more active than lidocaine, providing longer duration of complete anesthesia. Therefore, based on the obtained results of in silico tests, local anesthesia, and acute toxicity, a conclusion can be drawn that the experimental compounds need further extensive future investigations and possible modifications so that they can act as promising drug candidates.

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6

Ji, Jian, Ling-Yan Chen, Zi-Bin Qiu, Xinfeng Ren, and Ya Li. "Metal-Free Oxidative Coupling of Tetrahydroisoquinolines and 3-Fluorooxindoles on Water." Synthesis 52, no. 03 (October 21, 2019): 471–78. http://dx.doi.org/10.1055/s-0039-1690213.

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An efficient, metal-free oxidative coupling of tetrahydroisoquinolines and 3-fluorooxindoles on water has been developed. Using aqueous tert-butyl hydroperoxide as the oxidant, Et3N as the base, and water as the sole solvent, a variety of 3-fluorooxindoles fully substituted at the 3-position and containing a tetrahydroisoquinoline fragment has been successfully prepared in yields of up to 93% with an anti/syn stereoselectivity of up to 99:1 under very mild and safe reaction conditions.

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7

Lipeeva, Alla V., Arkady O. Brysgalov, Tatyana G. Tolstikova, and Elvira E. Shults. "Synthesis, Transformations and Characterization of 8 Aminomethyl Substituted Umbelliferones as Probable Anti-Arrhythmic Agents." Current Bioactive Compounds 15, no. 1 (February 6, 2019): 71–82. http://dx.doi.org/10.2174/1573407213666171030152601.

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Background: Coumarin and modified nitrogen heterocyclic nuclei show biological activity. Combining these into a hybrid molecule could lead to new pharmacological agents. A series of hybrid compounds combining coumarin and piperidine, piperazine, purine or tetrahydroisoquinoline moieties were synthesized and evaluated for anti-arrhythmic activity. Methods: The Mannich reaction of coumarins (peurutenicin, peucenol and 6-cyanoumbelliferrone) with formaldehyde and various amines, including several alkaloids – anabasine, theophylline or tetrahydroisoquinolines, proceeds by heating under reflux in dioxane in the presence of 4-dimethylaminopyridine. The Suzuki reaction of 6,8-disubstituted umbelliferone triflate was used for the introduction of an aryl substituent in position 7 of the the coumarin framework. Results: Twenty two novel coumarin-based Mannich bases were synthesized via introduction of functional aminomethyl group at position 8 of 6 substituted 7-hydroxy-2H-chromen-2-ones by Mannich reaction. The results illustrated that the C-6 and C-8 substituents’ effect was obvious in our designed system and there was a relationship between the structures and the anti-arrhythmic activity of the 6,7,8- trisubstituted coumarins. 8-(6,7-dimethoxy-1-(3,4,5-trimethoxyphenyl)-tetrahydroisoquinolinylmethyl)- substituted peucenol derivatives shown in vivo a pronounced and selective anti-arrhythmic activity on epinephrine arrhythmias in comparison with natural coumarin peucenol. The moderate toxicity of the new compound encouraged further design of therapeutically relevant analogues based on this novel type of coumarin- tetrahydroisoquinoline hybrids. Conclusion: We have developed a mild reaction protocol to synthesize new mannich products on the basis of substituted coumarins. The anti-arrhythmic activity of coumarin-tetrahydroisoquinoline hybrids was revealed. We report for the first time that coumarin containing 8-(1-(3,4,5-trimethoxyphenyl) tetrahydroisoquinolinyl)methyl) substituent offer a suitable scaffold for the development of novel anti-arrhythmic agents.

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8

Clark, Robin D., Jahangir, and James A. Langston. "Heteroatom-directed lateral lithiation: synthesis of isoquinoline derivatives from N-(tert-butoxycarbonyl)-2-methylbenzylamines." Canadian Journal of Chemistry 72, no. 1 (January 1, 1994): 23–30. http://dx.doi.org/10.1139/v94-005.

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Methodology for the preparation of isoquinoline derivatives from N-(tert-butoxycarbonyl)-2-methylbenzylamines (1) was developed. Conversion of 1 to the dilithio species followed by condensation with DMF afforded Boc-3-hydroxy-1,2,3,4-tetrahydroisoquinolines 3, which could be dehydrated to 1,2-dihydroisoquinolines 4. Hydrogenation of dihydro compounds 4 afforded the corresponding tetrahydroisoquinolines 5. Treatment of the dilithio species from 1 with N-methoxy-N-methylamides afforded ketones 14, which were converted to 3-substituted dihydro-isoquinoline 15, tetrahydroisoquinolines (16, 17), or isoquinolines (20).

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9

Mosca, Luciana, Carla Blarzino, Raffaella Coccia, Cesira Foppoli, and Maria Anna Rosei. "Melanins From Tetrahydroisoquinolines." Free Radical Biology and Medicine 24, no. 1 (January 1998): 161–67. http://dx.doi.org/10.1016/s0891-5849(97)00211-6.

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10

Arustamyan, Zh S., R. E. Margaryan, A. A. Aghekyan, G. A. Panosyan, G. S. Mkrtchyan, and R. E. Muradyan. "Synthesis and antiarrhythmic activity of a new benzodioxolsubstituted 4-spirocycloalkan(tetrahydropyran)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolines." Журнал органической химии 59, no. 11 (December 15, 2023): 1446–54. http://dx.doi.org/10.31857/s051474922311006x.

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By the reaction of 1-(3,4-dimethoxy)phenylcycloalkanmethan- and 4-(3,4-dimethoxyphenyl)tetrahydropyran-4-methanamines with benzo[ d ][1,3]dioxol-5-carbonyl chloride corresponding N -substituted benzo[ d ][1,3]dioxol-5-carboxamides were synthesized. Cyclization of the latter with phosphorus oxychloride gave dihydroisoquinolines reduced with sodium borohydride to the corresponding spiro-substituted tetrahydroisoquinolines, whose methylation according to Eschweiler-Clark reaction gave N -methyl derivatives. By condensation abovementioned amines with benzo[ d ][1,3]dioxol-5-carbaldehyde Schiff bases were synthesized. The reduction of the latter with sodium borohydride gave the corresponding secondary amines - non-cyclic analogues of tetrahydroisoquinolines, which undergo cyclization under the conditions of the Eschweiler-Clark reaction to form N -benzodioxolmethyl-substituted tetrahydroisoquinolines.

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11

Guo, Bin, and Hai-Chao Xu. "Electrocatalytic C(sp³)–H/C(sp)–H cross-coupling in continuous flow through TEMPO/copper relay catalysis." Beilstein Journal of Organic Chemistry 17 (October 28, 2021): 2650–56. http://dx.doi.org/10.3762/bjoc.17.178.

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Electrocatalytic dehydrogenative C(sp3)–H/C(sp)–H cross-coupling of tetrahydroisoquinolines with terminal alkynes has been achieved in a continuous-flow microreactor through 2,2,6,6-tetramethylpiperidine 1-oxyl (TEMPO)/copper relay catalysis. The reaction is easily scalable and requires low concentration of supporting electrolyte and no external chemical oxidants or ligands, providing straightforward and sustainable access to 2-functionalized tetrahydroisoquinolines.

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12

Barham, Joshua P., Matthew P. John, and John A. Murphy. "One-pot functionalisation of N-substituted tetrahydroisoquinolines by photooxidation and tunable organometallic trapping of iminium intermediates." Beilstein Journal of Organic Chemistry 10 (December 12, 2014): 2981–88. http://dx.doi.org/10.3762/bjoc.10.316.

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Nucleophilic trapping of iminium salts generated via oxidative functionalisation of tertiary amines is well established with stabilised carbon nucleophiles. The few reports of organometallic additions have limited scope of substrate and organometallic nucleophile. We report a novel, one-pot methodology that functionalises N-substituted tetrahydroisoquinolines by visible light-assisted photooxidation, followed by trapping of the resultant iminium ions with organometallic nucleophiles. This affords 1,2-disubstituted tetrahydroisoquinolines in moderate to excellent yields.

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13

Kole, Priyanka B., and Fateh V. Singh. "Versatile Synthesis of Functionalized Tetrahydroisoquinolines by Ring Transformation of 2H-Pyran-2-ones." Australian Journal of Chemistry 72, no. 7 (2019): 524. http://dx.doi.org/10.1071/ch19046.

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Functionalized tetrahydroisoquinolines are convenient precursors for the construction of numerous heterocyclic compounds of therapeutic importance. In this paper we have illustrated an efficient synthesis of highly substituted tetrahydroisoquinolines from 2H-pyran-2-ones via nucleophile-mediated ring transformation with tert-butyl-4-oxopiperidine-1-carboxylate followed by acid-mediated cleavage of the tert-butyloxycarbonyl group. The products were achieved smoothly in high yields with flexibility of various substituents.

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14

Jin, Yuan, Yasuhiro Honma, Hisashi Morita, Masamichi Miyagawa, and Takahiko Akiyama. "Enantioselective Synthesis of 1-Substituted 1,2,3,4-Tetrahydroisoquinolines through 1,3-Dipolar Cycloaddition by a Chiral Phosphoric Acid." Synlett 30, no. 13 (June 27, 2019): 1541–45. http://dx.doi.org/10.1055/s-0039-1690108.

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A new approach is described for the asymmetric synthesis of 1-substituted 1,2,3,4-tetrahydroisoquinolines that is based on the enantioselective 1,3-dipolar cycloaddition reaction of a nitrone and a vinyl ether in the presence of a chiral phosphoric acid that gives the chiral tetrahydroisoquinolines in high yields and with high enantioselectivities. 1H and 31P NMR analyses of the mixture of nitrone and chiral phosphoric acid suggest the formation of a 1:1 complex.

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15

Klein, Andreas Sebastian, Anna Christina Albrecht, and Jörg Pietruszka. "Chemoenzymatic One-Pot Process for the Synthesis of Tetrahydroisoquinolines." Catalysts 11, no. 11 (November 17, 2021): 1389. http://dx.doi.org/10.3390/catal11111389.

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1,2,3,4-Tetrahydroisoquinolines form a valuable scaffold for a variety of bioactive secondary metabolites and commercial pharmaceuticals. Due to the harsh or complex conditions of the conventional chemical synthesis of this molecular motif, alternative mild reaction pathways are in demand. Here we present an easy-to-operate chemoenzymatic one-pot process for the synthesis of tetrahydroisoquinolines starting from benzylic alcohols and an amino alcohol. We initially demonstrate the oxidation of 12 benzylic alcohols by a laccase/TEMPO system to the corresponding aldehydes, which are subsequently integrated in a phosphate salt mediated Pictet–Spengler reaction with m-tyramine. The reaction conditions of both individual reactions were analyzed separately, adapted to each other, and a straightforward one-pot process was developed. This enables the production of 12 1,2,3,4-tetrahydroisoquinolines with yields of up to 87% with constant reaction conditions in phosphate buffer and common laboratory glass bottles without the supplementation of any additives.

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16

HARA, HIROSHI, MASATOSHI MURAKATA, OSAMU HOSHINO, BUNSUKE UMEZAWA, and YOICHI IITAKA. "Studies on Tetrahydroisoquinolines. XXX. A synthesis of mixed tetrahydroisoquinoline dimers via p-quinol acetates." CHEMICAL & PHARMACEUTICAL BULLETIN 36, no. 5 (1988): 1627–37. http://dx.doi.org/10.1248/cpb.36.1627.

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17

HARA, HIROSHI, MASATOSHI MURAKATA, OSAMU HOSHINO, BUNSUKE UMEZAWA, and TSUTOMU INOUE. "Studies on tetrahydroisoquinolines. XXXI. A synthesis of tetrahydroisoquinoline dimers by intermolecular C-O coupling." CHEMICAL & PHARMACEUTICAL BULLETIN 36, no. 5 (1988): 1869–71. http://dx.doi.org/10.1248/cpb.36.1869.

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18

Dyachenko, I. V., V. D. Dyachenko, P. V. Dorovatovskii, V. N. Khrustalev, and V. G. Nenajdenko. "New Synthesis of Tetrahydroisoquinolines." Russian Journal of Organic Chemistry 58, no. 5 (May 2022): 657–62. http://dx.doi.org/10.1134/s1070428022050037.

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19

Ruff, Bettina M., S. Bräse, and Sarah E. O’Connor. "Biocatalytic production of tetrahydroisoquinolines." Tetrahedron Letters 53, no. 9 (February 2012): 1071–74. http://dx.doi.org/10.1016/j.tetlet.2011.12.089.

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20

Zeng, Linwei, Bo Huang, Yangyong Shen, and Sunliang Cui. "Multicomponent Synthesis of Tetrahydroisoquinolines." Organic Letters 20, no. 12 (May 29, 2018): 3460–64. http://dx.doi.org/10.1021/acs.orglett.8b01159.

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21

F.M, Tursunkhodzhaeva, and Azamatov A.A. "HARMACOLOGY OF 1,2,3,4-TETRAHYDROISOQUINOLINES." Journal of Research in Pharmacy 27_special_issue_7, no. 27_special_issue_7 (2023): 47. http://dx.doi.org/10.29228/jrp.604.

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22

HARA, HIROSHI, AKIRA TSUNASHIMA, HIROSHI SHINOKI, TOSHIFUMI AKIBA, OSAMU HOSHINO, and BUNSUKE UMEZAWA. "Studies on tetrahydroisoquinolines. XXVI. A biomimetic synthesis of 5-oxygenated 1,2,3,4-tetrahydroisoquinolines." CHEMICAL & PHARMACEUTICAL BULLETIN 34, no. 1 (1986): 66–70. http://dx.doi.org/10.1248/cpb.34.66.

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23

Chen, Lei, Chuanxi Sun, Guidong Feng, Min Cao, Shu-lei Zhao, Jun Yan, Ren-zhong Wan, and Lei Liu. "Direct oxidative C–H alkynylation of N-carbamoyl tetrahydroisoquinolines and dihydroisoquinolines." Organic & Biomolecular Chemistry 16, no. 15 (2018): 2792–99. http://dx.doi.org/10.1039/c8ob00373d.

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24

Tussing, Sebastian, Miriam Ohland, Garrit Wicker, Ulrich Flörke, and Jan Paradies. "Borane-catalyzed indole synthesis through intramolecular hydroamination." Dalton Transactions 46, no. 5 (2017): 1539–45. http://dx.doi.org/10.1039/c6dt04725d.

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25

Xi, Ruqi, Rahima Abdulla, Miaomiao Zhang, Zhurakulov Sherzod, Vinogradova Valentina Ivanovna, Maidina Habasi, and Yongqiang Liu. "Pharmacokinetic Study and Metabolite Identification of 1-(3′-bromophenyl)-heliamine in Rats." Pharmaceuticals 15, no. 12 (November 29, 2022): 1483. http://dx.doi.org/10.3390/ph15121483.

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Tetrahydroisoquinolines have been widely investigated for the treatment of arrhythmias. 1−(3′−bromophenyl)−heliamine (BH), an anti−arrhythmias agent, is a synthetic tetrahydroisoquinoline. This study focuses on the pharmacokinetic characterization of BH, as well as the identification of its metabolites, both in vitro and in vivo. A UHPLC−MS/MS method was developed and validated to quantify BH in rat plasma with a linear range of 1–1000 ng/mL. The validated method was applied to a pharmacokinetic study in rats. The maximum concentration Cmax (568.65 ± 122.14 ng/mL) reached 1.00 ± 0.45 h after oral administration. The main metabolic pathways appeared to be phase-I of demethylation, dehydrogenation, and epoxidation, and phase II of glucuronide and sulfate metabolites. Finally, a total of 18 metabolites were characterized, including 10 phase I metabolites and 8 phase II metabolites. Through the above studies, we have gained a better understanding of the absorption and metabolism of BH in vitro and in vivo, which will provide us with guidance for future in-depth studies on this compound.

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26

Haldar, Surajit, and Chandan K. Jana. "Direct (het)arylation of tetrahydroisoquinolines via a metal and oxidant free C(sp3)–H functionalization enabled three component reaction." Organic & Biomolecular Chemistry 17, no. 7 (2019): 1800–1804. http://dx.doi.org/10.1039/c8ob02309c.

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27

Ju, Shuyun, Mingxin Qian, Jing Li, Gang Xu, Lirong Yang, and Jianping Wu. "A biocatalytic redox cascade approach for one-pot deracemization of carboxyl-substituted tetrahydroisoquinolines by stereoinversion." Green Chemistry 21, no. 20 (2019): 5579–85. http://dx.doi.org/10.1039/c9gc02795e.

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28

Zhao, Hong, Wen He, Li Wei, and Mingzhong Cai. "A highly efficient heterogeneous copper-catalyzed three-component coupling of tetrahydroisoquinolines, aldehydes and 1-alkynes." Catalysis Science & Technology 6, no. 5 (2016): 1488–95. http://dx.doi.org/10.1039/c5cy01342a.

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29

Manna, Sudipta Kumar, and Gautam Panda. "Synthesis of enantiomerically enriched indolines and tetrahydroisoquinolines from (S)-amino acid-derived chiral carbocations: an easy access to (3S,4R)-demethoxy-3-isopropyl diclofensine." Org. Biomol. Chem. 12, no. 41 (2014): 8318–24. http://dx.doi.org/10.1039/c4ob00922c.

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30

Jiang, Huanfeng, Hanling Gao, Bifu Liu, and Wanqing Wu. "Palladium-catalyzed selective aminoamidation and aminocyanation of alkenes using isonitrile as amide and cyanide sources." Chem. Commun. 50, no. 97 (2014): 15348–51. http://dx.doi.org/10.1039/c4cc07743a.

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31

Kuwano, R., S. Ueno, and M. Ohtsubo. "Palladium-Catalyzed Synthesis of Tetrahydroisoquinolines." Synfacts 2009, no. 12 (November 20, 2009): 1324. http://dx.doi.org/10.1055/s-0029-1218223.

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32

Sasikumar, T. K., L. Qiang, W. L. Wu, D. A. Burnett, W. J. Greenlee, K. O’Neill, B. E. Hawes, M. van Heek, and M. Graziano. "Tetrahydroisoquinolines as MCH-R1 antagonists." Bioorganic & Medicinal Chemistry Letters 16, no. 18 (September 2006): 4917–21. http://dx.doi.org/10.1016/j.bmcl.2006.06.055.

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33

Ibañez, Adriana F., Graciela Y. Moltrasio Iglesias, and José M. Delfino. "Conformational analysis of 1,2,3,4-tetrahydroisoquinolines." Journal of Heterocyclic Chemistry 33, no. 2 (March 1996): 265–70. http://dx.doi.org/10.1002/jhet.5570330209.

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34

Meese, Claus O., and Thomas Ebner. "Synthesis of deuterated 1,2,3,4-tetrahydroisoquinolines." Journal of Labelled Compounds and Radiopharmaceuticals 25, no. 3 (March 1988): 335–43. http://dx.doi.org/10.1002/jlcr.2580250313.

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35

Jordaan, Maryam A., and Oluwakemi Ebenezer. "Biological Activities of Tetrahydroisoquinolines Derivatives." Journal of Organic and Pharmaceutical Chemistry 21, no. 1 (May 5, 2023): 20–38. http://dx.doi.org/10.24959/ophcj.23.268358.

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1,2,3,4-Tetrahydroisoquinoline (THIQ) is a common scaffold of many alkaloids isolated from several plants and mammalian species. THIQ derivatives possess a broad spectrum of biological activities, including antitumor, antitubercular, antitrypanosomal, antibacterial, anti-HIV, anti-inflammatory, anti-Alzheimer, and anticonvulsant ones.Aim. To cover updated studies on the biological properties of THIQ derivatives, as well as their structure-activity relationship (SAR), in order to highlight the effect of diverse functional groups responsible for the manifestation of the desired activity.Results and discussion. We have presented the review on biological activities of THIQ. The SAR studies show that the electron-donating, electron-withdrawing and some heterocyclic functional groups on the backbone plays a vital role in modulating the biological potential of the compounds synthesized.Conclusions. This review will help pharmaceutical researchers to synthesize novel and potent compounds containing THIQ scaffold.

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36

Kozekov, I. D., R. I. Koleva, and M. D. Palamareva. "ChemInform Abstract: New trans/cis Tetrahydroisoquinolines. Part 1. trans-2-Benzyl-3- (1-methyl-1H-pyrrol-2-yl) -4-substituted-1,2,3,4-tetrahydroisoquinolin-1-ones and Corresponding Tetrahydroisoquinolines." ChemInform 33, no. 28 (May 21, 2010): no. http://dx.doi.org/10.1002/chin.200228181.

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37

Ramanivas, T., G. Gayatri, D. Priyanka, V. L. Nayak, K. K. Singarapu, and A. K. Srivastava. "Stereoselective synthesis of functionalized 1,2,3,4-tetrahydroisoquinolines (THIQs) via highly diastereoselective Ugi three-component reactions (U3CRs) with chiral 3,4-dihydroisoquinolines (DHIQs)." RSC Advances 5, no. 90 (2015): 73373–80. http://dx.doi.org/10.1039/c5ra11144g.

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Wang, Changhong, Wei Zhou, Zhaojun Sun, Yuting Wang, Bin Zhang, and Yifu Yu. "Integrated selective nitrite reduction to ammonia with tetrahydroisoquinoline semi-dehydrogenation over a vacancy-rich Ni bifunctional electrode." Journal of Materials Chemistry A 9, no. 1 (2021): 239–43. http://dx.doi.org/10.1039/d0ta09590g.

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Liu, Wangsheng, Shasha Liu, Ruiwen Jin, Hao Guo, and Jinbo Zhao. "Novel strategies for catalytic asymmetric synthesis of C1-chiral 1,2,3,4-tetrahydroisoquinolines and 3,4-dihydrotetrahydroisoquinolines." Organic Chemistry Frontiers 2, no. 3 (2015): 288–99. http://dx.doi.org/10.1039/c4qo00294f.

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Pan, Xuan, and Zhanzhu Liu. "Synthesis of 3-aryl-3-benzazepines via aryne [1,2] Stevens rearrangement of 1,2,3,4-tetrahydroisoquinolines." Organic Chemistry Frontiers 5, no. 11 (2018): 1798–810. http://dx.doi.org/10.1039/c8qo00275d.

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Rahman, Iftakur, Bhaskar Deka, Ranjit Thakuria, Mohit L. Deb, and Pranjal K. Baruah. "l-Proline-catalyzed regioselective C1 arylation of tetrahydroisoquinolines through a multicomponent reaction under solvent-free conditions." Organic & Biomolecular Chemistry 18, no. 33 (2020): 6514–18. http://dx.doi.org/10.1039/d0ob01363c.

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Chen, Yunyun, and Gaofeng Feng. "Visible light mediated sp3 C–H bond functionalization of N-aryl-1,2,3,4-tetrahydroisoquinolines via Ugi-type three-component reaction." Organic & Biomolecular Chemistry 13, no. 14 (2015): 4260–65. http://dx.doi.org/10.1039/c5ob00201j.

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Gan, Shaolin, Yan Zeng, Jiaxin Liu, Junqi Nie, Cuifen Lu, Chao Ma, Feiyi Wang, and Guichun Yang. "Click-based conjugated microporous polymers as efficient heterogeneous photocatalysts for organic transformations." Catalysis Science & Technology 12, no. 4 (2022): 1202–10. http://dx.doi.org/10.1039/d1cy02076e.

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Gupta, Kankatala S. V., Daggupati V. Ramana, Botla Vinayak, Balasubramanian Sridhar, and Malapaka Chandrasekharam. "Copper-catalyzed regio and diastereoselective three component C–N, C–C and C–O bond forming reaction: oxidative sp3 C–H functionalization." New Journal of Chemistry 40, no. 7 (2016): 6389–95. http://dx.doi.org/10.1039/c5nj03707g.

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Wang, Chao-Ming, Dan Song, Peng-Ju Xia, Zhi-Peng Ye, Jun-An Xiao, Hao-Yue Xiang, Xiao-Qing Chen, and Hua Yang. "Photoredox-catalyzed direct aminoalkylation of isatins: diastereoselective access to 3-hydroxy-3-aminoalkylindolin-2-ones analogues." Organic Chemistry Frontiers 5, no. 10 (2018): 1608–12. http://dx.doi.org/10.1039/c8qo00201k.

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Zhao, Zheng-Le, Qing-Long Xu, Qing Gu, Xin-Yan Wu, and Shu-Li You. "Enantioselective synthesis of 4-substituted tetrahydroisoquinolines via palladium-catalyzed intramolecular Friedel–Crafts type allylic alkylation of phenols." Organic & Biomolecular Chemistry 13, no. 10 (2015): 3086–92. http://dx.doi.org/10.1039/c4ob02574a.

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Abstract:

Pd-catalyzed asymmetric intramolecular allylic alkylation reaction of phenols was developed, affording C4 substituted tetrahydroisoquinolines in moderate to excellent yields, enantioselectivity and regioselectivity.

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Zhang, Dan, Junwen Liu, Zhenghui Kang, Huang Qiu, and Wenhao Hu. "A rhodium-catalysed three-component reaction to access C1-substituted tetrahydroisoquinolines." Organic & Biomolecular Chemistry 17, no. 46 (2019): 9844–48. http://dx.doi.org/10.1039/c9ob02303h.

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Muramatsu, Wataru, Kimihiro Nakano, and Chao-Jun Li. "Direct sp3 C–H bond arylation, alkylation, and amidation of tetrahydroisoquinolines mediated by hypervalent iodine(iii) under mild conditions." Org. Biomol. Chem. 12, no. 14 (2014): 2189–92. http://dx.doi.org/10.1039/c3ob42354a.

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Llobat, Alberto, Jorge Escorihuela, Carmen Ramírez de Arellano, Santos Fustero, and Mercedes Medio-Simón. "Intramolecular rhodium-catalysed [2 + 2 + 2] cycloaddition of linear chiral N-bridged triynes: straightforward access to fused tetrahydroisoquinoline core." Organic & Biomolecular Chemistry 20, no. 12 (2022): 2433–45. http://dx.doi.org/10.1039/d2ob00340f.

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Yoo, Woo-Jin, and Shū Kobayashi. "Efficient visible light-mediated cross-dehydrogenative coupling reactions of tertiary amines catalyzed by a polymer-immobilized iridium-based photocatalyst." Green Chem. 16, no. 5 (2014): 2438–42. http://dx.doi.org/10.1039/c4gc00058g.

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