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Search for "tetrahydroquinoline" in Full Text gives 27 result(s) in Beilstein Journal of Organic Chemistry.

N-Boc-α-diazo glutarimide as efficient reagent for assembling N-heterocycle-glutarimide diads via Rh(II)-catalyzed N–H insertion reaction

  • Grigory Kantin,
  • Pavel Golubev,
  • Alexander Sapegin,
  • Alexander Bunev and
  • Dmitry Dar’in

Beilstein J. Org. Chem. 2023, 19, 1841–1848, doi:10.3762/bjoc.19.136

Graphical Abstract
  • varying characteristics were selected as substrates for the studied insertion reaction, encompassing both aromatic and non-aromatic compounds differing in the number and arrangement of nitrogen atoms (Scheme 3). Notably, several of these heterocycles, including tetrahydroquinoline, 1,2,4-triazole, and
  • regioselectivity of this reaction can be attributed to several factors, including steric hindrances to the attack of the nitrogen atom by the carbenoid. When reacting with tetrahydroquinoline (with insignificant steric shielding of the N-nucleophilic center), the product of N–H insertion 6x was obtained in good
  • yield. As a side process, а carbenoid's repeated attack at the 6-position of the tetrahydroquinoline ring of compound 6x was observed according to NMR data. Introducing a bromine atom to block the 6-position led to a significant increase in the target product 6y yield. The decomposition of diazo reagent
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Published 07 Dec 2023

Recent advances in the asymmetric phosphoric acid-catalyzed synthesis of axially chiral compounds

  • Alemayehu Gashaw Woldegiorgis and
  • Xufeng Lin

Beilstein J. Org. Chem. 2021, 17, 2729–2764, doi:10.3762/bjoc.17.185

Graphical Abstract
  • % (R)-CPA 2, the benzyl-substituted 3-alkenylindole 81 (dienophile) was subjected to a Povarov cycloaddition with the commonly used imine 80, giving the 2,3,4-tetrahydroquinoline as a single diastereomer in high yield and enantioselectivity and finely tolerating the high steric requirements necessary
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Published 15 Nov 2021

Copper-catalyzed monoselective C–H amination of ferrocenes with alkylamines

  • Zhen-Sheng Jia,
  • Qiang Yue,
  • Ya Li,
  • Xue-Tao Xu,
  • Kun Zhang and
  • Bing-Feng Shi

Beilstein J. Org. Chem. 2021, 17, 2488–2495, doi:10.3762/bjoc.17.165

Graphical Abstract
  • functionalities, such as ester 4f, cyano 4g and ketal 4i, were well tolerated. Unfortunately, 1,2,3,4-tetrahydroquinoline (2k) was proved unreactive under our conditions, probably due to the steric hindrance. Thiomorpholine (2l) was compatible with this reaction, albeit with significantly dropped yield (29
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Published 28 Sep 2021

N-tert-Butanesulfinyl imines in the asymmetric synthesis of nitrogen-containing heterocycles

  • Joseane A. Mendes,
  • Paulo R. R. Costa,
  • Miguel Yus,
  • Francisco Foubelo and
  • Camilla D. Buarque

Beilstein J. Org. Chem. 2021, 17, 1096–1140, doi:10.3762/bjoc.17.86

Graphical Abstract
  • tetrahydroquinoline alkaloids (−)-angustureine (107) and (−)-cuspareine (108) reported by Sirvent et al. [119]. The diastereoselective addition of a Grignard reagent was a key step in this methodology. The addition proceeded with high diastereoselectivity in toluene, and the attack of the Grignard reagent occurred on
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Published 12 May 2021

Synthetic reactions driven by electron-donor–acceptor (EDA) complexes

  • Zhonglie Yang,
  • Yutong Liu,
  • Kun Cao,
  • Xiaobin Zhang,
  • Hezhong Jiang and
  • Jiahong Li

Beilstein J. Org. Chem. 2021, 17, 771–799, doi:10.3762/bjoc.17.67

Graphical Abstract
  • transfer takes place, giving radicals 33 and 34. Radical 34 is quenched by oxygen, and radical 33 attacks 31 in order to form radical 35. Intermediate 36 is achieved by cyclization of radical 35, followed by hydrogen-atom removal, providing the cis-tetrahydroquinoline 32 (Scheme 11). It is worth noting
  • perfluoroalkylated pyrimidines 26 initiated by an EDA complex. Synthesis of phenanthridine derivative 29 initiated by an EDA complex. Synthesis of cis-tetrahydroquinoline derivative 32 initiated by an EDA complex. Mechanism of the synthesis of cis-tetrahydroquinoline derivative 32. Synthesis of phenanthridine
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Published 06 Apr 2021

Total synthesis of pyrrolo[2,3-c]quinoline alkaloid: trigonoine B

  • Takashi Nishiyama,
  • Erina Hamada,
  • Daishi Ishii,
  • Yuuto Kihara,
  • Nanase Choshi,
  • Natsumi Nakanishi,
  • Mari Murakami,
  • Kimiko Taninaka,
  • Noriyuki Hatae and
  • Tominari Choshi

Beilstein J. Org. Chem. 2021, 17, 730–736, doi:10.3762/bjoc.17.62

Graphical Abstract
  • synthesis of the 2,3-dihydroquinolin-4-one moiety of trigonoine B (1) by cycloamination of 22c (Scheme 4). The Buchwald–Hartwig amination of 22c was conducted in the presence of t-BuONa, BINAP, and Pd2(dba)3·CHCl3; however, the desired tetrahydroquinoline 23 was not obtained and only 22c was recovered. We
  • and desilylation, the electrocyclization of 29a proceeded smoothly to afford the desired 4-aminopyrroloquinoline 30a in 68% yield. Subsequently, the cycloamination of 30a in the presence of Pd(OAc)2, Cu(OAc)2, and K2CO3 gave tetrahydroquinoline 31 in 25% yield. However, although attempts were made to
  • -aminopyrroloquinoline 30b was synthesized from 2-(pyrrol-3-yl)aniline 25 and 3-(2-iodophenyl)propyl isocyanate (26b) in 3 steps using the same procedure as described for 30a. The subsequent cycloamination of 30b gave tetrahydroquinoline 31 in 73% yield, thus resulting in a significantly improved yield. Finally, the
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Published 16 Mar 2021

Convenient access to pyrrolidin-3-ylphosphonic acids and tetrahydro-2H-pyran-3-ylphosphonates with multiple contiguous stereocenters from nonracemic adducts of a Ni(II)-catalyzed Michael reaction

  • Alexander N. Reznikov,
  • Dmitry S. Nikerov,
  • Anastasiya E. Sibiryakova,
  • Victor B. Rybakov,
  • Evgeniy V. Golovin and
  • Yuri N. Klimochkin

Beilstein J. Org. Chem. 2020, 16, 2073–2079, doi:10.3762/bjoc.16.174

Graphical Abstract
  • octahydroindole [10], tetrahydroquinoline [11], tetrahydroisoquinoline [11][12], β-carboline [13], morpholine [14], and isoindoline [15] moieties have been developed. Obtained in an enantiomerically pure form, phosphonoproline and its analogues [16][17][18][19] were among the first compounds in this series
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Published 25 Aug 2020

Heterogeneous photocatalysis in flow chemical reactors

  • Christopher G. Thomson,
  • Ai-Lan Lee and
  • Filipe Vilela

Beilstein J. Org. Chem. 2020, 16, 1495–1549, doi:10.3762/bjoc.16.125

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Published 26 Jun 2020

Recent applications of porphyrins as photocatalysts in organic synthesis: batch and continuous flow approaches

  • Rodrigo Costa e Silva,
  • Luely Oliveira da Silva,
  • Aloisio de Andrade Bartolomeu,
  • Timothy John Brocksom and
  • Kleber Thiago de Oliveira

Beilstein J. Org. Chem. 2020, 16, 917–955, doi:10.3762/bjoc.16.83

Graphical Abstract
  • of these protocols, as demonstrated by the nonmetallated TPP which did not work. The tetrahydroquinoline products were obtained in up to 1.1 gram-scale, after 20 h under blue LED irradiation (18 W), for both N-alkyl/aryl maleimides (57–92% yields) and the p-substituted N,N-dimethylanilines (78–97
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Published 06 May 2020

Synthesis of pyrrolo[1,2-a]quinolines by formal 1,3-dipolar cycloaddition reactions of quinolinium salts

  • Anthony Choi,
  • Rebecca M. Morley and
  • Iain Coldham

Beilstein J. Org. Chem. 2019, 15, 1480–1484, doi:10.3762/bjoc.15.149

Graphical Abstract
  • explore the diversity of products that could be obtained from these adducts, we carried out a reduction of the alkene in compounds 9 and 10 by using hydrogen and palladium on charcoal (Scheme 4). This provides the tetrahydroquinoline adducts 11 and 12. Additionally, and in contrast, oxidation of the
  • ). The adducts could be reduced, oxidised, or could undergo Suzuki–Miyaura coupling to give different substituted dihydro- and tetrahydroquinoline derivatives. Single crystal X-ray structure for 7c. Single crystal X-ray structure for 9. Reaction of ketone 1 with electron-deficient alkenes 2. Reactions of
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Published 03 Jul 2019

Practical synthetic strategies towards lipophilic 6-iodotetrahydroquinolines and -dihydroquinolines

  • David R. Chisholm,
  • Garr-Layy Zhou,
  • Ehmke Pohl,
  • Roy Valentine and
  • Andrew Whiting

Beilstein J. Org. Chem. 2016, 12, 1851–1862, doi:10.3762/bjoc.12.174

Graphical Abstract
  • temperatures. Coupling these strongly electron-donating scaffolds to electron-accepting moieties caused the resulting structures to exhibit strong fluorescence. Keywords: cyclisation; dihydroquinoline; elimination; reduction; tetrahydroquinoline; Introduction Tetrahydroquinolines (THQ) and dihydroquinolines
  • free of charge from The Cambridge Crystallographic Data Centre via http://www.ccdc.cam.ac.uk/getstructures. Tetrahydroquinoline (THQ) and dihydroquinoline (DHQ) scaffolds to be synthesised. Simulated structure of 22 indicates a flattened quinoline-like structure. Hartree–Fock calculations (3-21G*) were
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Published 16 Aug 2016

Palladium-catalyzed picolinamide-directed iodination of remote ortho-C−H bonds of arenes: Synthesis of tetrahydroquinolines

  • William A. Nack,
  • Xinmou Wang,
  • Bo Wang,
  • Gang He and
  • Gong Chen

Beilstein J. Org. Chem. 2016, 12, 1243–1249, doi:10.3762/bjoc.12.119

Graphical Abstract
  • iodination, and Cu-catalyzed C−N cyclization enables a streamlined synthesis of tetrahydroquinolines bearing diverse substitution patterns. Keywords: iodination; palladium; remote C–H activation; tetrahydroquinoline; Introduction Tetrahydroquinoline (THQ) is an important N-heterocyclic scaffold found in
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Published 17 Jun 2016

Recent advances in copper-catalyzed asymmetric coupling reactions

  • Fengtao Zhou and
  • Qian Cai

Beilstein J. Org. Chem. 2015, 11, 2600–2615, doi:10.3762/bjoc.11.280

Graphical Abstract
  • (Scheme 16). In 2014, Cai et al. [46] applied the desymmetrization strategy to construct chiral cyano-bearing all-carbon quaternary stereocenters, affording 1,2,3,4-tetrahydroquinoline analogues in good yields and excellent enantioselectivities (Scheme 17). The same group also observed that achiral
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Published 15 Dec 2015

An intramolecular C–N cross-coupling of β-enaminones: a simple and efficient way to precursors of some alkaloids of Galipea officinalis

  • Hana Doušová,
  • Radim Horák,
  • Zdeňka Růžičková and
  • Petr Šimůnek

Beilstein J. Org. Chem. 2015, 11, 884–892, doi:10.3762/bjoc.11.99

Graphical Abstract
  • leading to the above-mentioned tetrahydroquinoline moiety. The methodology is superior to the methods published to date. Keywords: C–N cross-coupling; copper; enaminone; palladium; tetrahydroquinoline; Introduction Galipea officinalis Hancock is a Venezuelan shrub, the bark (angostura bark) of which is
  • used in folk medicine for stimulation in the cure of some paralytic diseases [1] and for the treatment of fever [2]. In addition, antituberculous [3], antiplasmodial and cytotoxic [2] properties have been also described. The active constituents of the bark are mainly tetrahydroquinoline alkaloids such
  • longer reaction time. Compound 3b was transformed into 1b using the above-mentioned conditions (Table 2, entry 9) only in 20% conversion. Having the conditions for the successful cyclization of enaminones 3a,e to tetrahydroquinoline 1a in hand, we applied them to other enaminones 3. In all of these cases
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Published 27 May 2015

Eosin Y-catalyzed visible-light-mediated aerobic oxidative cyclization of N,N-dimethylanilines with maleimides

  • Zhongwei Liang,
  • Song Xu,
  • Wenyan Tian and
  • Ronghua Zhang

Beilstein J. Org. Chem. 2015, 11, 425–430, doi:10.3762/bjoc.11.48

Graphical Abstract
  • tends to form the iminium ion by one electron oxidation (Scheme 1) [39][40][41]. In the context of this research background, we investigated the α-aminoalkyl radical route to achieve the aerobic oxidative cyclization of N,N-dimethylanilines with maleimides to form the corresponding tetrahydroquinoline
  • light (two 9 W blue LEDs) at room temperature. Gratifyingly, the desired product tetrahydroquinoline 3a was obtained in 82% yield after 18 h (Table 1, entry 1). We screened a number of metal-free organic dyes for photocatalysts. Of the dyes screened, Eosin Y showed the highest efficiency (Table 1, entry
  • 1), Rose Bengal gave a slightly lower yield (Table 1, entry 2), whereas Methylene Blue and Fluorescein gave poor yields (Table 1, entries 3 and 4). Under an O2 atmosphere, the yield of tetrahydroquinoline product 3a was decreased to 77% (Table 1, entry 5). When the molar proportion of 1a and 2a was
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Published 01 Apr 2015

Natural phenolic metabolites with anti-angiogenic properties – a review from the chemical point of view

  • Qiu Sun,
  • Jörg Heilmann and
  • Burkhard König

Beilstein J. Org. Chem. 2015, 11, 249–264, doi:10.3762/bjoc.11.28

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  • ) vanillin, 1,2,3,4-tetrahydroquinoline, HOAc, H3BO3, DMF, Δ, 4 h. Exemplary synthesis of MAC representatives. Reagents and conditions: (a) 40% KOH, EtOH, 5 °C; stirring 10 h, rt. X = C, N; R = OH, OMe, Cl, F. Synthesis of ellagic acid (7). Reagents and conditions: (a) H2SO4, CH3OH; (b) (1) o-chloranil, Et2O
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Published 16 Feb 2015

Lewis acid-catalyzed redox-neutral amination of 2-(3-pyrroline-1-yl)benzaldehydes via intramolecular [1,5]-hydride shift/isomerization reaction

  • Chun-Huan Jiang,
  • Xiantao Lei,
  • Le Zhen,
  • Hong-Jin Du,
  • Xiaoan Wen,
  • Qing-Long Xu and
  • Hongbin Sun

Beilstein J. Org. Chem. 2014, 10, 2892–2896, doi:10.3762/bjoc.10.306

Graphical Abstract
  • amines were also good substrates for this reaction, affording the desired products (3q, 3r, 3s) in good to high yields (77–98% yields) with DCE as the solvent under reflux conditions. The reaction with indoline, tetrahydroquinoline, and tetrahydroisoquinoline could also be realized to give products 3t
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Published 05 Dec 2014

Preparation of neuroprotective condensed 1,4-benzoxazepines by regio- and diastereoselective domino Knoevenagel–[1,5]-hydride shift cyclization reaction

  • László Tóth,
  • Yan Fu,
  • Hai Yan Zhang,
  • Attila Mándi,
  • Katalin E. Kövér,
  • Tünde-Zita Illyés,
  • Attila Kiss-Szikszai,
  • Balázs Balogh,
  • Tibor Kurtán,
  • Sándor Antus and
  • Péter Mátyus

Beilstein J. Org. Chem. 2014, 10, 2594–2602, doi:10.3762/bjoc.10.272

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  • Chemistry, University of Debrecen, H-4010 Debrecen, Hungary Porfirin Ltd., Mikszáth K. u. 7. III/3, 4032 Debrecen, Hungary 10.3762/bjoc.10.272 Abstract Condensed O,N-heterocycles containing tetrahydro-1,4-benzoxazepine and tetrahydroquinoline moieties were prepared by a regio- and diastereoselective domino
  • derivative afforded three condensed O,N-heterocycles containing tetrahydro-1,4-benzoxazepine and tetrahydroquinoline moieties. trans-Diastereoselectivity of the cyclizations was determined by the correlation of 3JH,H coupling constants with the geometry of the computed conformers, while (2R,15aR) absolute
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Published 06 Nov 2014

Aza-Diels–Alder reaction between N-aryl-1-oxo-1H-isoindolium ions and tert-enamides: Steric effects on reaction outcome

  • Amitabh Jha,
  • Ting-Yi Chou,
  • Zainab ALJaroudi,
  • Bobby D. Ellis and
  • T. Stanley Cameron

Beilstein J. Org. Chem. 2014, 10, 848–857, doi:10.3762/bjoc.10.81

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  • major highlight of this work. Results and Discussion Our literature search revealed that although tert-enamides have been used as dienophiles for the Povarov reaction to build 1,2,3,4-tetrahydroquinoline blocks [25][26][37], there were no reports of their usage in the inverse electron demand hetero
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Published 14 Apr 2014

Studies on the interaction of isocyanides with imines: reaction scope and mechanistic variations

  • Ouldouz Ghashghaei,
  • Consiglia Annamaria Manna,
  • Esther Vicente-García,
  • Marc Revés and
  • Rodolfo Lavilla

Beilstein J. Org. Chem. 2014, 10, 12–17, doi:10.3762/bjoc.10.3

Graphical Abstract
  • isatinimines led to the formation of the spiro-azetidines 3k (14%) and 3l (28%, Table 1, entries 11 and 12). Remarkably, in the former case an intramolecular cyclization of the nitrilium ion upon the electron rich p-methoxyphenyl group took place and led to the formation of the bis(imino)tetrahydroquinoline 8
  • nitrilium intermediate, in agreement with a Sorensen report (Scheme 4, route iii) [21]. Finally, the imino-nitrilium cation can be trapped by an aromatic ring when using isatin imines, leading to bis(imino)tetrahydroquinoline 8, (Scheme 4, route iv). In a reaction using a large isocyanide excess, a triple
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Published 06 Jan 2014

A combined continuous microflow photochemistry and asymmetric organocatalysis approach for the enantioselective synthesis of tetrahydroquinolines

  • Erli Sugiono and
  • Magnus Rueping

Beilstein J. Org. Chem. 2013, 9, 2457–2462, doi:10.3762/bjoc.9.284

Graphical Abstract
  • for the synthesis of tetrahydroquinoline from readily available 2-aminochalcone provides an attractive alternative to the existing procedures and serves as a basis for further exploration of this new concept. Photocyclization–reduction of 2-aminochalcone. Experimental setup of continuous-flow
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Published 13 Nov 2013

Simple synthesis of pyrrolo[3,2-e]indole-1-carbonitriles

  • Adam Trawczyński,
  • Robert Bujok,
  • Zbigniew Wróbel and
  • Krzysztof Wojciechowski

Beilstein J. Org. Chem. 2013, 9, 934–941, doi:10.3762/bjoc.9.107

Graphical Abstract
  • cyanoborohydride [4]. On the other hand there are many methods of synthesis of pyrrolo[3,2-e]indoles such as the copper-catalyzed transformation of tetrahydroquinoline derivatives [4], photochemical cyclization of 1,2-bis(2-pyrrolo)ethylenes [5], the Fischer indole synthesis from indol-5-ylhydrazones [3], or a
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Published 15 May 2013

Facile synthesis of functionalized tetrahydroquinolines via domino Povarov reactions of arylamines, methyl propiolate and aromatic aldehydes

  • Jing Sun,
  • Hong Gao,
  • Qun Wu and
  • Chao-Guo Yan

Beilstein J. Org. Chem. 2012, 8, 1839–1843, doi:10.3762/bjoc.8.211

Graphical Abstract
  • reaction; tetrahydroquinoline; Introduction The Diels–Alder reaction is recognized as a powerful reaction in synthetic strategies for the production of natural and unnatural polycarbocycles and polyheterocycles [1][2][3]. Therefore, the hetero-Diels–Alder reactions and domino reaction procedures have been
  • enantiomerically enriched 4-amino-tetrahydroquinolines [43][44]. In this work our aim is to describe the domino Povarov reaction with both in situ formed aldimine and in situ generated β-enamino ester for the facile synthesis of the functionalized tetrahydroquinoline. Results and Discussion It is known that the
  • overnight to give the desired β-enamino ester. Then, benzaldehyde and p-toluenesulfonic acid was introduced in the reaction system and the sequential reaction was finished in 48 hours at room temperature monitored by TLC. After workup we were pleased to find that the functionalized tetrahydroquinoline 1c
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Published 26 Oct 2012

Organocatalytic C–H activation reactions

  • Subhas Chandra Pan

Beilstein J. Org. Chem. 2012, 8, 1374–1384, doi:10.3762/bjoc.8.159

Graphical Abstract
  • (−)-camphorsulfonic acid (CSA) in 1,1,2-trichloroethane (TCE) at 20 °C provided the desired product in highest enantioselectivity (89% ee). Under the optimized conditions, a range of ortho-(dialkylamino)cinnamaldehydes were employed and chiral tetrahydroquinoline products 14 were obtained in moderate to good yields
  • excellent enantioselectivities (70–97% ee, mostly above 90% ee) were achieved for different tetrahydroquinoline products 16 having gem-methyl ester groups (Scheme 12). For substrates containing one N-benzyl group and one N-ethyl group, binaphthol-based catalyst 17 was used; however, no chemoselectivity (16j
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Published 27 Aug 2012

Continuous-flow catalytic asymmetric hydrogenations: Reaction optimization using FTIR inline analysis

  • Magnus Rueping,
  • Teerawut Bootwicha and
  • Erli Sugiono

Beilstein J. Org. Chem. 2012, 8, 300–307, doi:10.3762/bjoc.8.32

Graphical Abstract
  • increasing the residence time to 60 min (Table 3, entry 3 versus entry 2). The catalyst loading can be decreased to 0.5 mol % without loss of reactivity and selectivity; the desired tetrahydroquinoline was isolated in 96% yield with 94% enantiomeric excess (Table 3, entry 5). A further decrease of catalyst
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Published 23 Feb 2012
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