- Metal-free reduction of unsaturated carbonyls, quinones, and pyridinium salts with tetrahydroxydiboron/water
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A series of unsaturated carbonyls, quinones, and pyridinium salts have been effectively reduced to the corresponding saturated carbonyls, dihydroxybenzenes, and hydropyridines in moderate to high yields with tetrahydroxydiboron/water as a mild, convenient, and metal-free reduction system. Deuterium-labeling experiments have revealed this protocol to be an exclusive transfer hydrogenation process from water. This journal is
- Li, Tiejun,Peng, Henian,Tang, Wenjun,Tian, Duanshuai,Xu, Guangqing,Yang, He
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p. 4327 - 4337
(2021/05/31)
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- Iodination/Amidation of the N-Alkyl (Iso)quinolinium Salts
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The NaIO4-mediated sequential iodination/amidation reaction of N-alkyl quinolinium iodide salts has been first developed. This cascade process provides an efficient way to rapidly synthesize 3-iodo-N-alkyl quinolinones with high regioselectivity and good functional group tolerance. This protocol was also amenable to the isoquinolinium salts, thus providing a complementary method for preparing the 4-iodo-N-alkyl isoquinolinones.
- Tang, Juan,Chen, Xue,Zhao, Chao-Qun,Li, Wen-Jing,Li, Shun,Zheng, Xue-Li,Yuan, Mao-Lin,Fu, Hai-Yan,Li, Rui-Xiang,Chen, Hua
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supporting information
p. 716 - 730
(2020/12/22)
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- Regioselective Direct C-H Trifluoromethylation of Pyridine
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A highly efficient and regioselective direct C-H trifluoromethylation of pyridine based on an N-methylpyridine quaternary ammonium activation strategy has been developed. A variety of trifluoromethylpyridines can be obtained in good yield and excellent re
- Yang, Xiao,Sun, Rui,Li, Shun,Zheng, Xueli,Yuan, Maolin,Xu, Bin,Jiang, Weidong,Chen, Hua,Fu, Haiyan,Li, Ruixiang
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supporting information
p. 7108 - 7112
(2020/10/02)
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- Electrochemical regioselective selenylation/oxidation of: N-alkylisoquinolinium salts via double C(sp2)-H bond functionalization
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An efficient, novel, and environmentally friendly electrochemical regioselective selenylation/oxidation of N-alkylisoquinolinium salts via double C(sp2)-H bond functionalization under undivided electrolytic conditions has been developed. A series of selenide isoquinolones were easily accessed through this sustainable and clean electrochemical system. The present protocol was further extended to afford selenide quinolones and 1,3-dimethyl-1H-benzo[d]imidazol-2(3H)-ones. Furthermore, antiviral bioassays demonstrated that compound 3j exhibited excellent antiviral activity against tobacco mosaic virus (TMV), and its inhibition rate was up to 90%. This journal is
- Liu, Xiang,Wang, Yajun,Song, Dan,Wang, Yuhan,Cao, Hua
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supporting information
p. 15325 - 15328
(2020/12/23)
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- Synthesis of 4-Iodoisoquinolin-1(2 H)-ones by a Dirhodium(II)-Catalyzed 1,4-Bisfunctionalization of Isoquinolinium Iodide Salts
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An efficient Rh2(II,II)-catalyzed reaction has been developed under mild conditions. This synthetic method proceeds through iodination/oxidation of readily available isoquinolinium iodide salts under aerobic conditions with good to excellent yields. 4-Iodoisoquinolin-1(2H)-ones are important building blocks for biologically and medicinally important compounds. The developed methodology was applied to the gram-scale synthesis of a key intermediate in the synthesis of the CRTH2 antagonist CRA-680.
- Fang, Zaixiang,Wang, Yi,Wang, Yuanhua
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supporting information
p. 434 - 438
(2019/01/23)
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- Carbene-catalyzed aerobic oxidation of isoquinolinium salts: Efficient synthesis of isoquinolinones
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A mild and environmentally friendly carbene-catalyzed aerobic oxidation of isoquinolinium salts was successfully realized. Accordingly, a diverse set of isoquinolinones and phenanthridinones was efficiently prepared in good to excellent yields. The mechanistic study indicates that the formation of an aza-Breslow intermediate is the crucial step in this transformation. This reaction features ambient air as the sole oxidant and oxygen source, a broad substrate scope, and excellent functional-group tolerance and proceeds under mild reaction conditions. Furthermore, a highly efficient synthesis of bioactive molecules and natural products including N-methylcrinasiadine, N-isopentylcrinasiadine, N-phenethylcrinasiadine, isoindolo[2,1-b]isoquinolin-5(7H)-one, PJ-34, rac-Gusanlung D, rosettacin, 8-oxopseudopalmatine and ilicifoline B was accomplished.
- Wang, Guanjie,Hu, Wanyao,Hu, Zhouli,Zhang, Yuxia,Yao, Wei,Li, Lin,Fu, Zhenqian,Huang, Wei
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supporting information
p. 3302 - 3307
(2018/07/29)
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- Construction of Tropane Derivatives by the Organocatalytic Asymmetric Dearomatization of Isoquinolines
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A chiral-NHC-catalyzed highly diastereo- and enantioselective dearomatizing double Mannich reaction of isoquinolines was developed that provides a powerful and straightforward synthetic route toward substituted tropane derivatives with four contiguous ste
- Xu, Jin-Hui,Zheng, Sheng-Cai,Zhang, Ji-Wei,Liu, Xin-Yuan,Tan, Bin
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supporting information
p. 11834 - 11839
(2016/11/16)
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- Cucurbit[7]uril complexations of bis(isoquinolinium)alkane dications in aqueous solution
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The 1:1 and 2:1 host-guest complexation of a series of 1,n- bis(isoquinolinium)alkane dications (Iq(CH2)nIq 2+, n = 2, 4, 5, 6, 8, 9, 10 and 12, and Iq(p-xylene)Iq2+) by cucurbit[7]uril (CB[7]) in aqueous solution has been investigated by 1H NMR spectroscopy and ESI mass spectrometry. The site of binding of the first CB[7] is dependent on the nature of the central linker group, with encapsulation of the p-xylene group or the polymethylene chain when n = 6-10.With shorter (n = 2-5) or longer (n = 12) chains, the first CB[7] binds over an isoquinolinium group. With a second CB[7], the binding of the central group is abandoned in favour of the CB[7] hosts encapsulating the two cationic isoquinolinium termini. The 1:1 and 2:1 host-guest stability constants are related to modes of binding and the nature of the central linkers, and are compared with dicationic guests bearing different terminal groups.
- Kwok, Julian C.,Macartney, Donal H.
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p. 182 - 191
(2014/05/06)
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- Synthesis of CF3-substituted 1,2,3,4-tetrahydroisoquinolines and 1,2,3,6-tetrahydropyridines
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A three-step method for the preparation of CF3-substituted 1,2,3,4-tetrahydroisoquino-lines and 1,2,3,6-tetrahydropyridines has been suggested. The first step includes alkylation of isoquinoline or 4-methylpyridine at the nitrogen atom with the
- Chernyshov, I. Yu.,Levin,Dilman,Belyakov,Struchkova,Tartakovsky
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experimental part
p. 2102 - 2107
(2011/06/26)
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- Efficient macrocyclization achieved via conformational control using intermolecular noncovalent π-cation/arene interactions
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Quinolinium salt 3 is an effective additive that acts as a conformation control element (CCE) to promote macrocyclization to form rigid cyclophanes via olefin metathesis or Glaser-Hay coupling, which do not cyclize in the absence of the additive. The additives are easily synthesized and highly modifiable and have solubility profiles which allow for simple recovery via filtration.
- Bolduc, Philippe,Jacques, Alexandre,Collins, Shawn K.
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supporting information; experimental part
p. 12790 - 12791
(2010/11/04)
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- Syntheses of quaternary carbon-containing oxazatricycle and spiropyran libraries via multicomponent reactions and their molecular switching properties
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A practical protocol for the preparation of parallel solution-phase libraries of the quaternary carbon-containing oxazatricycles and spiropyrans is reported. Target compounds were obtained in moderate to excellent yields by an Et3N-mediated mul
- Lin, Chi-Hui,Chen, Jhih-Rong,Yang, Ding-Yah
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body text
p. 119 - 124
(2010/10/19)
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- NOVEL MONOAMINE RE-UPTAKE INHIBITOR
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The present invention relates to novel compounds of Formula (I), their pharmaceutically acceptable derivatives, tautomeric forms, stereoisomers including R and S isomers, polymorphs, prodrugs, metabolites, salts or solvates thereof. The invention also rel
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Page/Page column 32
(2009/10/22)
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- Transfer hydrogenation of isoquinolinium salts catalyzed by a rhodium complex
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Regio- and chemoselective transfer hydrogenation of isoquinolinium salts catalyzed by [Cp*RhCl2]2 using HCOOH-Et3N (5:2) as a hydrogen source was realized. A variety of N-methyl- and N-benzyl-1,2,3,4-tetrahydroisoquinoline
- Wu, Jiashou,Liao, Jian,Zhu, Jin,Deng, Jingen
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p. 2059 - 2062
(2008/02/05)
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- Recognition of quaternary ammonium salts with tetrapeptides containing α-aminoisobutyric acid as a conformational constraint
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Tetrapeptides Trp-Aib-Gly-Leu-NH-Ar (Aib:α-aminoisobutyric acid, 2-amino-2-methylpropanoic acid, Ar = phenyl or 3,5-dimethylphenyl) were synthesized. The peptides bound quaternary ammonium salts as guests in CDCl3. For every guest, the binding constant K of the peptide host which has a 3,5-dimethylphenyl group was larger than that of the host which has a phenyl group. ROESY analysis of the complex revealed that the N+-CH3 groups of the guests were close to the aromatic moieties of the host in the complex. The charge in cation guests, the φ-basicity of the host, and the turn conformation of the peptides were important factors for the complexation.
- Yanagihara, Ryoji,Katoh, Masaki,Hanyuu, Masayuki,Miyazawa, Toshifumi,Yamada, Takashi
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p. 551 - 556
(2007/10/03)
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- Azole additions upon azinium salts
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The additions of pyrrole and indole upon N-acetyl- and N-alkylpyridinium, quinolinium or isoquinolinium sails are reported. The resulting dihydroazines are either isolated or oxidised to the more stable aromatic compounds. The use of a two-phase system wa
- Lavilla, Rodolfo,Gotsens, Teresa,Guerrero, Marta,Masdeu, Carme,Santano, M. Carmen,Minguillon, Cristina,Bosch, Joan
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p. 13959 - 13968
(2007/10/03)
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- Biomimetic catalysis of SN2 reactions through cation-π interactions. The role of polarizability in catalysis
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Cyclophane hosts 1 and 2 have been shown to be effective catalysts for both the alkylation of quinoline structures to produce quinolinium salts and the dealkylation of sulfonium salts to produce sulfides. Thus, reactions that develop positive charge in the transition state and reactions that destroy positive charge are accelerated. The former observation is not surprising, given the well-documented ability of these hosts to bind cations through the cation-π interaction. The catalysis of the dealkylation reactions, however, along with several other observations, suggests that some other factor is involved in the catalysis. It is proposed that the high polarizability of the transition states is well matched to the very polarizable hosts and that this contributes to the catalysis.
- McCurdy, Alison,Jimenez, Leslie,Stauffer, David A.,Dougherty, Dennis A.
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p. 10314 - 10321
(2007/10/02)
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- Tetrahydroisoquinolines. Part 2. Synthesis of 4-Substituted N-Methyl-1,2,3,4-tetrahydroisoquinolines via Regio- and Stereo-selective Elaboration of Tricarbonyl(N-methyl-1,2,3,4-tetrahydroisoquinoline)chromium
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Thermolysis of hexacarbonylchromium with N-methyltetrahydroisoquinoline generates the tricarbonyl-(N-methyltetrahydroisoquinoline)chromium complex (4).The 4-exo proton of complex (4) can be regio- and stereo-selectively removed with butyl-lithium and replaced stereoselectivity with retention of configuration by a variety of electrophiles .Oxidative decomplexation generates quantitatively the corresponding 4-methyl, ethyl, benzyl, deuterio, phenyl, hydroxy, and (1-hydroxy-1-methylethyl)-N-methyltetrahydroisoquinolines.
- Blagg, Julian,Coote, Steven J.,Davies, Stephen G.,Mobbs, Bryan E.
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p. 2257 - 2262
(2007/10/02)
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- Synthetic Applications of Lithiation Reactions : Part XV - New Syntheses of Isochinolines and a Novel Synthesis of Tetrahydropalmatine
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New syntheses of the isoquinoline ring system, involving organometallic intermediates, are described.This is illustrated by a novel synthesis of the alkaloid, tetrahydropalmatine, in simple steps.
- Narasimhan, N. S.,Ranade, A. C.,Bhide, B. H.
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p. 439 - 440
(2007/10/02)
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