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Journal articles on the topic 'Dihydroisoquinolines'

Author: Grafiati

Published: 4 June 2021

Last updated: 16 February 2022

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1

Puerto Galvis, Carlos, Mario Macías, and Vladimir Kouznetsov. "Unexpected PF6 Anion Metathesis during the Bischler–Napieralski Reaction: Synthesis of 3,4-Dihydroisoquinoline Hexafluorophosphates and Their Tetrahydroisoquinoline Related Alkaloids." Synthesis 51, no. 09 (2019): 1949–60. http://dx.doi.org/10.1055/s-0037-1610684.

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A series of N-phenethylcinnamamides were subjected to the Bischler–Napieralski reaction to furnish diverse 1-styryl-3,4-dihydroisoquinolines. We noticed that the desired products were unstable when the reaction was performed under conventional solvent conditions. However, when [bmim]PF6 was used as the reaction media, the nature of the Bischler–Napieralski reaction promoted an unusual in situ ionic interchange between this ionic liquid and the dihydroisoquinoline core that led to the stabilization of the desired 1-styryl-3,4-dihydroisoquinolines, allowing their isolation as hexafluorophosphate

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2

Mwansa, Joseph M., Matthew J. Stirling, and Michael I. Page. "Changing the kinetic order of enantiomer formation and distinguishing between iminium ion and imine as the reactive species in the asymmetric transfer hydrogenation of substituted imines using a cyclopentadienyl iridium (III) complex." Pure and Applied Chemistry 92, no. 1 (2020): 107–21. http://dx.doi.org/10.1515/pac-2019-0222.

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AbstractThe iridium (III) complex of pentamethylcyclopentadiene and (S,S) or (R,R)-1,2-diphenyl-N′-tosylethane-1,2-diamine is an effective catalyst for the asymmetric transfer hydrogenation of imines under acidic conditions. However, the enantiomeric excess (ee) of the product amines from the reduction of 1-methyl-3,4-dihydroisoquinolines in either acetonitrile or dichloromethane, decreases exponentially. The dominant cause of the enantioselectivity is the difference in kinetic order of the formation of the two enantiomers with the S-enantiomer being formed in a first-order process whereas tha

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3

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 (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 tetrahydroisoqu

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4

Flores-Ferrándiz, Jesús, Nicholas Carter, Maria José González-Soria, et al. "Stereoselective synthesis of 1,3-disubstituted dihydroisoquinolines vial-phenylalanine-derived dihydroisoquinoline N-oxides." Organic & Biomolecular Chemistry 16, no. 38 (2018): 6961–68. http://dx.doi.org/10.1039/c8ob02007h.

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Addition of Grignard reagents and alkenes to readily available (S)-3-(hydroxymethyl)-3,4-dihydroisoquinoline-2-oxide allow the highly stereoselective synthesis of a range of 1,3-disubstituted tetrahydroisoquinolines.

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5

Facchetti, Giorgio, Michael S. Christodoulou, Eleonora Binda, Marco Fusè, and Isabella Rimoldi. "Asymmetric Hydrogenation of 1-aryl substituted-3,4-Dihydroisoquinolines with Iridium Catalysts Bearing Different Phosphorus-Based Ligands." Catalysts 10, no. 8 (2020): 914. http://dx.doi.org/10.3390/catal10080914.

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Starting from the chiral 5,6,7,8-tetrahydroquinolin-8-ol core, a series of amino-phosphorus-based ligands was realized. The so-obtained amino-phosphine ligand (L1), amino-phosphinite (L2) and amino-phosphite (L3) were evaluated in iridium complexes together with the heterobiaryl diphosphines tetraMe-BITIOP (L4), Diophep (L5) and L6 and L7 ligands, characterized by mixed chirality. Their catalytic performance in the asymmetric hydrogenation (AH) of the model substrate 6,7-dimethoxy-1-phenyl-3,4-dihydroisoquinoline 1a led us to identify Ir-L4 and Ir-L5 catalysts as the most effective. The applic

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6

Chen, Lei, Chuanxi Sun, Guidong Feng, et al. "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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7

Fathimath Salfeena, C. T., K. T. Ashitha, and B. S. Sasidhar. "BF3·Et2O mediated one-step synthesis of N-substituted-1,2-dihydropyridines, indenopyridines and 5,6-dihydroisoquinolines." Organic & Biomolecular Chemistry 14, no. 43 (2016): 10165–69. http://dx.doi.org/10.1039/c6ob02133f.

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8

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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9

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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10

Voskressensky, L. G., T. N. Borisova, M. D. Matveeva, et al. "A novel multi-component approach to the synthesis of pyrrolo[2,1-a]isoquinoline derivatives." RSC Advances 6, no. 78 (2016): 74068–71. http://dx.doi.org/10.1039/c6ra15810b.

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11

Perekalin, Dmitry S., Evgeniya A. Trifonova, Alina A. Komarova, and Denis Chusov. "Variability of Rhodium(III)-Catalyzed Reactions of Aromatic Oximes with Alkenes." Synlett 31, no. 11 (2020): 1117–20. http://dx.doi.org/10.1055/s-0040-1707961.

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Acetophenone oxime reacts with various alkenes in the presence of the rhodium catalyst [Cp*RhCl2]2 (2.5 mol%; Cp* = pentamethylcyclopentadienyl) and 1,1,1,3,3,3-hexafluoropropan-2-ol as an important cosolvent. Styrene, aliphatic terminal alkenes, and strained cyclic alkenes gave the corresponding substituted dihydroisoquinolines in yields of 50–99%. On the other hand, alkenes containing functional groups close to the double bond gave a variety of different products. The reactions of acetophenone oxime with styrene or dec-1-ene in the presence of the chiral catalyst [(C5H2 t Bu2CH2 t Bu)RhI2]2

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12

Varlamov, A. V., N. I. Guranova, R. A. Novikov, et al. "Synthesis of novel fluorescent 12a-aryl substituted indoxylisoquinolines via aryne-induced domino process." RSC Advances 6, no. 15 (2016): 12642–46. http://dx.doi.org/10.1039/c5ra25323c.

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13

Xiong, Zhuang, Panyuan Cai, Yingshuang Mei, and Jian Wang. "Access to 1-amino-3,4-dihydroisoquinolines via palladium-catalyzed C–H bond aminoimidoylation reaction from functionalized isocyanides." RSC Advances 9, no. 72 (2019): 42072–76. http://dx.doi.org/10.1039/c9ra09139d.

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14

Chaudhari, Tohasib Yusub, Urvashi Urvashi, Sandeep K. Ginotra, Pooja Yadav, Gulshan Kumar, and Vibha Tandon. "Regioselective synthesis of functionalized dihydroisoquinolines from o-alkynylarylaldimines via the Reformatsky reaction." Organic & Biomolecular Chemistry 14, no. 41 (2016): 9896–906. http://dx.doi.org/10.1039/c6ob01790h.

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15

Asao, N., and K. Iso. "Three-Component Synthesis of 1,2-Dihydroisoquinolines." Synfacts 2006, no. 11 (2006): 1101. http://dx.doi.org/10.1055/s-2006-949424.

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16

Lantos, Ivan, and Haralambos E. Katerinopoulos. "Synthetic transformations of cyclopropyl annulated dihydroisoquinolines." Canadian Journal of Chemistry 69, no. 6 (1991): 1033–37. http://dx.doi.org/10.1139/v91-152.

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Isomeric 3-cyano-3-methyl-2-acetyl-cycloprop[c]isoquinolines, 5 and 6, were prepared by alkylation and cyclopropanation of Reissert compounds and their reactions under basic conditions were examined. Both compounds, under the influence of methoxide, yielded isoquinoline derived products resulting from cleavage of the peripheral C—C bond. The results are postulated to derive from attack of the methoxide on the acyl carbonyl, forming a tetrahedral adduct that undergoes ring opening. Key words: cyclopropanation, ring opening, tetrahedral complex, pyramidalization.

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17

Mikhailovskii, A. G. "Synthesis of 1-aroyl-3,4-dihydroisoquinolines." Chemistry of Heterocyclic Compounds 36, no. 2 (2000): 223. http://dx.doi.org/10.1007/bf02283558.

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18

Aleksandrov, B. B., M. S. Gavrilov, R. Z. Dautova, et al. "Biological activity of fluorinated 3,4-dihydroisoquinolines." Pharmaceutical Chemistry Journal 26, no. 1 (1992): 57–58. http://dx.doi.org/10.1007/bf00773197.

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19

Urvashi, Urvashi, Gaurav K. Rastogi, Sandeep K. Ginotra, Alka Agarwal, and Vibha Tandon. "An expedient approach to 1,2-dihydroisoquinoline derivatives via cobalt catalysed 6-endo dig cyclization followed by Mannich condensation of o-alkynylarylaldimines." Organic & Biomolecular Chemistry 13, no. 4 (2015): 1000–1007. http://dx.doi.org/10.1039/c4ob02036g.

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A highly effective 6-endo dig cyclisation of o-alkynyl aldimines to 1,2-dihydroisoquinolines has been described via direct and nitro Mannich condensation using inexpensive and readily available cobalt chloride as catalyst.

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20

Jahangir, Jahangir, David B. MacLean, and Herbert L. Holland. "Aza analogues of protoberberine and phthalideisoquinoline alkaloids." Canadian Journal of Chemistry 64, no. 6 (1986): 1031–35. http://dx.doi.org/10.1139/v86-173.

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Anions derived from furo[3,4-c]pyridin-3(1H)-one, by treatment with lithium diisopropylamide, react with substituted, 3,4-dihydroisoquinolines and 2-methyl-3,4-dihydroisoquinolinium salts yielding nitrogen analogues of the protoberberine and phthalideisoquinoline alkaloids, respectively.

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21

Unnava, Ramanjaneyulu, Kapil Chahal, and Kallu Rajender Reddy. "Synthesis of substituted 1,2-dihydroisoquinolines via Ni(ii) and Cu(i)/Ag(i) catalyzed double nucleophilic addition of arylamines to ortho-alkynyl donor–acceptor cyclopropanes (o-ADACs)." Organic & Biomolecular Chemistry 19, no. 27 (2021): 6025–29. http://dx.doi.org/10.1039/d1ob00760b.

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Synthesis of substituted 1,2-dihydroisoquinolines via double nucleophilic addition of primary arylamines to ortho-alkynyl donor–acceptor cyclopropanes (o-ADACs) in the presence of a catalytic Ni(ii) and Cu(i)/Ag(i) system has been developed.

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22

Glushkov, V. A., V. I. Karmanov, and Yu V. Shklyaev. "Symmetrical and Unsymmetrical Bis-1,1′-(3,4-dihydroisoquinolines)." Chemistry of Heterocyclic Compounds 41, no. 4 (2005): 475–80. http://dx.doi.org/10.1007/s10593-005-0174-8.

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23

Jørgensen, K., K. Frisch, A. Landa, and S. Saaby. "Enantioselective Synthesis of 1,2-Dihydroisoquinolines and 1,2-Dihydrophthalazines." Synfacts 2006, no. 01 (2005): 0024. http://dx.doi.org/10.1055/s-2005-921690.

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24

Sodeoka, M., N. Sasamoto, C. Dubs, and Y. Hamashima. "Pd(II)-Catalyzed Addition of Malonates to Dihydroisoquinolines." Synfacts 2007, no. 2 (2007): 0177. http://dx.doi.org/10.1055/s-2006-955845.

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25

Mikhailovskii, A. G. "ChemInform Abstract: Synthesis of 1-Aroyl-3,4-dihydroisoquinolines." ChemInform 31, no. 47 (2000): no. http://dx.doi.org/10.1002/chin.200047142.

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26

Sosnovskikh, V. Ya, B. I. Usachev, and Yu V. Shklyaev. "Reactions of 1,3,3-trimethyl-3,4-dihydroisoquinolines with polyhaloalkanonitriles." Russian Chemical Bulletin 53, no. 6 (2004): 1248–52. http://dx.doi.org/10.1023/b:rucb.0000042281.14105.53.

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27

Berg, Michael A. G., and Harry W. Gibson. "Cyanoacylation of 1-substituted isoquinolines and 3,4-dihydroisoquinolines." Journal of Organic Chemistry 57, no. 2 (1992): 748–50. http://dx.doi.org/10.1021/jo00028a064.

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28

Aleksandrov, B. B., M. Yu Dormidontov, V. S. Shklyaev, and Yu V. Shklyaev. "Synthesis of 1-substituted-3,3-dimethyl-3,4-dihydroisoquinolines." Chemistry of Heterocyclic Compounds 27, no. 5 (1991): 523–25. http://dx.doi.org/10.1007/bf00473999.

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29

Glushkov, V. A., Yu S. Rozhkova, M. I. Vakhrin, and Yu V. Shklyaev. "1-R-3,3-dialkyl-6,7-ethylenedioxy-3,4-dihydroisoquinolines." Chemistry of Heterocyclic Compounds 41, no. 8 (2005): 1022–26. http://dx.doi.org/10.1007/s10593-005-0272-7.

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30

Shklyaev, Yu V., V. A. Glushkov, N. B. Belogub, and I. L. Misyura. "Reaction of 1-methylthio-3,4-dihydroisoquinolines with amines." Chemistry of Heterocyclic Compounds 32, no. 6 (1996): 689–95. http://dx.doi.org/10.1007/bf01164868.

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31

Tauber, Johannes, Dennis Imbri, Vanessa C. Colligs, and Till Opatz. "Zugänge zu Isomeren und Verwandten der Lamellarin-Alkaloide / Approach to Isomers and Structural Relatives of the Lamellarin Alkaloids." Zeitschrift für Naturforschung B 69, no. 5 (2014): 627–40. http://dx.doi.org/10.5560/znb.2014-4045.

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Synthetic approaches to novel isomers and unprecedented structural relatives of the lamellarin alkaloids are reported. During our studies on methods to construct the lamellarin skeleton, we found the condensation of chroman-4-one derivatives with 1-benzyl-3,4-dihydroisoquinolines or the Pdcatalyzed cyclocarbonylation of o-halogenated precursors followed by Baeyer-Villiger oxidation to be unsuitable. Nevertheless, these routes produced interesting structural relatives of the natural alkaloids.

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32

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 (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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33

Jahangir, Michael A. Brook, David B. MacLean, and Herbert L. Holland. "8H-Isoquino[2,1-b][2,7]naphthyridin-8-ones: synthesis of the Alangium alkaloids, alangimaridine and alangimarine." Canadian Journal of Chemistry 65, no. 10 (1987): 2362–68. http://dx.doi.org/10.1139/v87-394.

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It is shown that 3,4-dihydroisoquinolines are activated toward nucleophilic attack by reaction with trimethylsilyl trifluoromethanesulfonate. The complex so formed reacts readily with the lithio derivative of 3-cyano-4-methyl-5-vinylpyridine, affording in a single step a tetracyclic amidine from which a lactam is obtained by hydrolysis. These reactions have been applied to the synthesis of the Alangium alkaloids, (±)-alangimaridine and alangimarine.

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34

Sasamoto, Naoki, Christian Dubs, Yoshitaka Hamashima, and Mikiko Sodeoka. "Pd(II)-Catalyzed Asymmetric Addition of Malonates to Dihydroisoquinolines." Journal of the American Chemical Society 128, no. 43 (2006): 14010–11. http://dx.doi.org/10.1021/ja065646r.

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35

Hamri, W., O. O. Shyshkina, T. M. Tarasiuk, et al. "One-Pot Domino Synthesis of 3-Amino-1,2-dihydroisoquinolines." Journal of Heterocyclic Chemistry 52, no. 5 (2014): 1373–76. http://dx.doi.org/10.1002/jhet.2241.

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36

Zhao, Sihan, Shaobing Cheng, Hui Liu, Jiayan Zhang, Weicheng Yuan, and Xiaomei Zhang. "Expedient Synthesis of Dihydroisoquinolines by Cascade Annulation of Nitrovinylbenzoquinone." ChemistrySelect 5, no. 15 (2020): 4478–80. http://dx.doi.org/10.1002/slct.202000589.

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37

Smolyak, A. A., L. D. Konyushkin, S. I. Firgang, and Yu V. Shklyaev. "Synthesis of 3-methyl-3,4-dihydroisoquinolines based on myristicin." Russian Journal of Organic Chemistry 52, no. 12 (2016): 1812–16. http://dx.doi.org/10.1134/s1070428016120174.

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38

Mikhailovskii, A. G., A. S. Yusov, and O. V. Gashkova. "Thiocarbamoylation of 1,3,3-trimethyl-3,4-dihydroisoquinolines with benzoyl isothiocyanate." Russian Journal of Organic Chemistry 51, no. 12 (2015): 1818–19. http://dx.doi.org/10.1134/s1070428015120349.

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39

Mikhailovskii, A. G., and M. I. Vahrin. "Synthesis of 3,3-Dialkyl-1-(3-coumarinyl)-3,4-dihydroisoquinolines." Chemistry of Heterocyclic Compounds 40, no. 8 (2004): 1036–38. http://dx.doi.org/10.1023/b:cohc.0000046694.99902.41.

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40

Polygalova, N. N., A. G. Mikhailovskii, V. V. Udodov, A. I. Mikhalev, and M. I. Vakhrin. "Synthesis of 3,3-dialkyl-1-(3-pyridyl)-3,4-dihydroisoquinolines." Chemistry of Heterocyclic Compounds 43, no. 8 (2007): 1024–28. http://dx.doi.org/10.1007/s10593-007-0160-4.

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41

Aksenov, N. A., V. V. Malyuga, G. M. Abakarov, D. A. Aksenov, L. G. Voskressensky, and A. V. Aksenov. "Synthesis of 3,4-dihydroisoquinolines using nitroalkanes in polyphosphoric acid." Russian Chemical Bulletin 68, no. 5 (2019): 1047–51. http://dx.doi.org/10.1007/s11172-019-2518-z.

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42

Wang, Long, Zhi-Rong Guan, and Ming-Wu Ding. "One-pot synthesis of 1H-isochromenes and 1,2-dihydroisoquinolines by a sequential isocyanide-based multicomponent/Wittig reaction." Organic & Biomolecular Chemistry 14, no. 8 (2016): 2413–20. http://dx.doi.org/10.1039/c5ob02405f.

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43

Ben Salah, Hassen, Maëelle Carraz, and Majed Kammoun. "Synthesis and cytotoxic activity of a novel dihydroisoquinoline-derived hydroxamic acid." JOURNAL OF ADVANCES IN CHEMISTRY 10, no. 4 (2014): 2648–53. http://dx.doi.org/10.24297/jac.v10i4.5503.

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Naturally occurring hydroxamic acid derivatives are biosynthesized by microorganisms (siderophores) and plants (benzoxazinoids). Recent developments in drug related research have highlighted the promising biological and pharmacological properties that the hydroxamic acid function may offer for the enhancement of therapeutic applications. This study reports on the full synthesis of a new dihydroisoquinoline hydroxamic acid (2-Hydroxy-3,3-dimethyl-7-nitro-3,4-dihydroisoquinolin-1(2H)-one). It also describes its cytotoxicity with regard to the human hepatocarcinoma cell line Hep3B.

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44

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 (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

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45

Urabe, Hirokazu, Masahito Yamagishi, Azusa Ishii, and Takeshi Hata. "Facile Preparation of 1,2-Dihydroisoquinolines from N-Benzylsulfonamides and Bromoacetylenes." HETEROCYCLES 90, no. 2 (2015): 847. http://dx.doi.org/10.3987/com-14-s(k)72.

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46

Asao, Naoki, Kentaro Iso, Salprima Yudha S., and _. Menggenbateer. "A Facile Synthesis of 1,2-Dihydroisoquinolines by Three-Component Reaction." HETEROCYCLES 74, no. 1 (2007): 649. http://dx.doi.org/10.3987/com-07-s(w)49.

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47

Ji, Xiang, Zheng Huang, and Jean-Philip Lumb. "Synthesis of 1,2-Dihydroisoquinolines by a Modified Pomeranz–Fritsch Cyclization." Journal of Organic Chemistry 85, no. 2 (2019): 1062–72. http://dx.doi.org/10.1021/acs.joc.9b02987.

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48

Min, Lin, Weiguang Yang, Yunxiang Weng, Weiping Zheng, Xinyan Wang, and Yuefei Hu. "A Method for Bischler–Napieralski-Type Synthesis of 3,4-Dihydroisoquinolines." Organic Letters 21, no. 8 (2019): 2574–77. http://dx.doi.org/10.1021/acs.orglett.9b00534.

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49

Saá, Carlos, Alejandro Varela-Fernández, and Jesús Varela. "Formation of Indoles, Dihydroisoquinolines, and Dihydroquinolines by Ruthenium-Catalyzed Heterocyclizations." Synthesis 44, no. 21 (2012): 3285–95. http://dx.doi.org/10.1055/s-0032-1316539.

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50

Roy, Tarun Kumar, Biswajit Parhi, and Prasanta Ghorai. "Cinchonamine Squaramide Catalyzed Asymmetric aza-Michael Reaction: Dihydroisoquinolines and Tetrahydropyridines." Angewandte Chemie 130, no. 30 (2018): 9541–45. http://dx.doi.org/10.1002/ange.201805020.

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