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Search for "isoquinolines" in Full Text gives 45 result(s) in Beilstein Journal of Organic Chemistry.

Synthesis of spiroindolenines through a one-pot multistep process mediated by visible light

  • Francesco Gambuti,
  • Jacopo Pizzorno,
  • Chiara Lambruschini,
  • Renata Riva and
  • Lisa Moni

Beilstein J. Org. Chem. 2024, 20, 2722–2731, doi:10.3762/bjoc.20.230

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  • indole alkaloids. Here, we develop a novel approach for the one-pot multistep synthesis of different spiro[indole-isoquinolines]. The protocol proposed involves the visible light mediated oxidation of N-aryl tertiary amines using bromochloroform with the generation of a reactive iminium species, which
  • compound 2 to the iminium ion 1a, cannot be ruled out (see Supporting Information File 1). Conclusion In conclusion, we have developed a novel visible light-promoted synthesis of spiro[indole-isoquinolines] employing simple and readily available starting materials. Our one-pot four-step synthesis allows
  • and t-BuNC conducted under optimized conditions. Synthesis of spiro[indole-heterocycles]. Synthetic strategy for the new synthesis of 2,3-diaminoindolenines [21] and spiro[indole-isoquinolines]. Scope of the synthesis of spiro[indole-THIQs]. aα-aminoamidine 2b has been isolated (54%) too; bα
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Published 29 Oct 2024

The Groebke–Blackburn–Bienaymé reaction in its maturity: innovation and improvements since its 21st birthday (2019–2023)

  • Cristina Martini,
  • Muhammad Idham Darussalam Mardjan and
  • Andrea Basso

Beilstein J. Org. Chem. 2024, 20, 1839–1879, doi:10.3762/bjoc.20.162

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Published 01 Aug 2024

Rapid construction of tricyclic tetrahydrocyclopenta[4,5]pyrrolo[2,3-b]pyridine via isocyanide-based multicomponent reaction

  • Xiu-Yu Chen,
  • Ying Han,
  • Jing Sun and
  • Chao-Guo Yan

Beilstein J. Org. Chem. 2024, 20, 1436–1443, doi:10.3762/bjoc.20.126

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  • -aza-1,3-butadienes [40][41][42][43][44]. Recently, we have found that the three-component reaction of isoquinolines, dialkyl but-2-ynediaotes and 5,6-unsubstituted 1,4-dihydropyridines afforded functionalized isoquinolino[1,2-f][1,6]naphthyridines in good yields and with high diastereoselectivity via
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Published 28 Jun 2024

Decarboxylative 1,3-dipolar cycloaddition of amino acids for the synthesis of heterocyclic compounds

  • Xiaofeng Zhang,
  • Xiaoming Ma and
  • Wei Zhang

Beilstein J. Org. Chem. 2023, 19, 1677–1693, doi:10.3762/bjoc.19.123

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  • bioactive compounds and natural products such as PB1-5 [74], lixivaptan, and (+)-anthramycin (Figure 5) [73]. Stepwise synthesis of pyrrolo[2,1-a]isoquinolines A stepwise synthesis involving [3 + 2] cycloaddition, N-allylation and Heck reactions has been developed for the synthesis of pyrrolo[2,1-a
  • ]isoquinolines. The reaction of 2-bromobenzaldehydes, 2-aminoisobutyric acid, and maleimides in MeCN under the catalysis of AcOH at 110 °C for 6 h afforded the cycloaddition products 26. The purified intermediates were used for the one-pot N-allylation with allyl bromide to afford intermediate 25 followed by a
  • pyrrolo[2,1-a]isoquinolines and hexahydropyrrolo[2,1-a]isoquinolines. Bioactive tetrahydropyrrolothiazoles. Aminoester- and amino acid-based AMYs for single and double [3+2] cycloadditions. Formation of semi-stabilized AMYs B1 from pyrrolidines. Cyclic amine-based AMYs A3 and B1 for [3 + 2] cycloadditions
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Published 06 Nov 2023

Non-noble metal-catalyzed cross-dehydrogenation coupling (CDC) involving ether α-C(sp3)–H to construct C–C bonds

  • Hui Yu and
  • Feng Xu

Beilstein J. Org. Chem. 2023, 19, 1259–1288, doi:10.3762/bjoc.19.94

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  • , pyrazines, pyridines, quinolines, isoquinolines, benzothiazoles, benzoquinones, etc. Under the reaction conditions, various ethers such as 1,4-dioxane, tetrahydropyran, tetrahydrofuran, diethyl ether, etc. are suitable substrates. Immediately thereafter, various photocatalytic catalysts were developed for
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Published 06 Sep 2023

Photoredox catalysis harvesting multiple photon or electrochemical energies

  • Mattia Lepori,
  • Simon Schmid and
  • Joshua P. Barham

Beilstein J. Org. Chem. 2023, 19, 1055–1145, doi:10.3762/bjoc.19.81

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Published 28 Jul 2023

The unique reactivity of 5,6-unsubstituted 1,4-dihydropyridine in the Huisgen 1,4-diploar cycloaddition and formal [2 + 2] cycloaddition

  • Xiu-Yu Chen,
  • Hui Zheng,
  • Ying Han,
  • Jing Sun and
  • Chao-Guo Yan

Beilstein J. Org. Chem. 2023, 19, 982–990, doi:10.3762/bjoc.19.73

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  • Xiu-Yu Chen Hui Zheng Ying Han Jing Sun Chao-Guo Yan College of Chemistry & Chemical Engineering, Yangzhou University, Jiangsu, Yangzhou 225002, China 10.3762/bjoc.19.73 Abstract The three-component reaction of isoquinolines, dialkyl acetylenedicarboxylates, and 5,6-unsubstituted 1,4
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Published 29 Jun 2023

Pyridine C(sp2)–H bond functionalization under transition-metal and rare earth metal catalysis

  • Haritha Sindhe,
  • Malladi Mounika Reddy,
  • Karthikeyan Rajkumar,
  • Akshay Kamble,
  • Amardeep Singh,
  • Anand Kumar and
  • Satyasheel Sharma

Beilstein J. Org. Chem. 2023, 19, 820–863, doi:10.3762/bjoc.19.62

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  • the use of pyridines for the formation of quinolines and isoquinolines, an oxidant-dependent rhodium-catalyzed C–H annulation of pyridines with alkynes was reported by Li and co-workers [105] in 2011 for the direct synthesis of quinolines 180 and isoquinolines 181 involving a two-fold C–H activation
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Published 12 Jun 2023

Me3Al-mediated domino nucleophilic addition/intramolecular cyclisation of 2-(2-oxo-2-phenylethyl)benzonitriles with amines; a convenient approach for the synthesis of substituted 1-aminoisoquinolines

  • Krishna M. S. Adusumalli,
  • Lakshmi N. S. Konidena,
  • Hima B. Gandham,
  • Krishnaiah Kumari,
  • Krishna R. Valluru,
  • Satya K. R. Nidasanametla,
  • Venkateswara R. Battula and
  • Hari K. Namballa

Beilstein J. Org. Chem. 2021, 17, 2765–2772, doi:10.3762/bjoc.17.186

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  • catalyst [36][37][38][39][40]. However, pre-functionalization of isoquinolines to the corresponding halogenated isoquinolines is the main limitation associated with these protocols as they require noxious halogenated acids for their starting materials preparation. Alternative strategies include, amination
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Published 16 Nov 2021

Recent advances in the tandem annulation of 1,3-enynes to functionalized pyridine and pyrrole derivatives

  • Yi Liu,
  • Puying Luo,
  • Yang Fu,
  • Tianxin Hao,
  • Xuan Liu,
  • Qiuping Ding and
  • Yiyuan Peng

Beilstein J. Org. Chem. 2021, 17, 2462–2476, doi:10.3762/bjoc.17.163

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  • powerful nitrogen source for the synthesis of various N-heterocycles, such as isoquinolines, quinolines, pyridines, pyrroles, indoles, azoles, and azepines [40][41][42][43][44][45]. 1,3-Enyne, as a powerful Michael acceptor, is a wonderful synthon for the synthesis of N-heterocycles via tandem addition and
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Published 22 Sep 2021

Halides as versatile anions in asymmetric anion-binding organocatalysis

  • Lukas Schifferer,
  • Martin Stinglhamer,
  • Kirandeep Kaur and
  • Olga García Macheño

Beilstein J. Org. Chem. 2021, 17, 2270–2286, doi:10.3762/bjoc.17.145

Graphical Abstract
  • ) [35]. During this early period, the group of Jacobsen also reported an asymmetric thiourea-catalyzed Reissert reaction of isoquinolines 21 (Scheme 5a) [36]. The mechanism proceeds by initial activation of the isoquinoline via N-acylation and subsequent dearomatization by a nucleophilic attack in the
  • , that Reissert dearomatizations of N-heteroarenes, especially of isoquinolines [36], and nucleophilic addition to 1-chloroisochromanes [38] have become benchmark reactions in the context of anion-binding catalysis. Besides reports of thiourea-catalyzed reactions with different nucleophiles [39][40], the
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Published 01 Sep 2021

On the application of 3d metals for C–H activation toward bioactive compounds: The key step for the synthesis of silver bullets

  • Renato L. Carvalho,
  • Amanda S. de Miranda,
  • Mateus P. Nunes,
  • Roberto S. Gomes,
  • Guilherme A. M. Jardim and
  • Eufrânio N. da Silva Júnior

Beilstein J. Org. Chem. 2021, 17, 1849–1938, doi:10.3762/bjoc.17.126

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Published 30 Jul 2021

Free-radical cyclization approach to polyheterocycles containing pyrrole and pyridine rings

  • Ivan P. Mosiagin,
  • Olesya A. Tomashenko,
  • Dar’ya V. Spiridonova,
  • Mikhail S. Novikov,
  • Sergey P. Tunik and
  • Alexander F. Khlebnikov

Beilstein J. Org. Chem. 2021, 17, 1490–1498, doi:10.3762/bjoc.17.105

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  • could be performed only with AlCl3 under harsh conditions and, therefore, cannot be used for the preparation of compounds with acid-sensitive substituents. In addition, the debenzylation of 1-benzyl-3-arylpyrido[2,1-a]pyrrolo[3,2-c]isoquinolines A was found to accompany by isomerization to 2-aryl
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Published 23 Jun 2021

Deoxygenative C2-heteroarylation of quinoline N-oxides: facile access to α-triazolylquinolines

  • Geetanjali S. Sontakke,
  • Rahul K. Shukla and
  • Chandra M. R. Volla

Beilstein J. Org. Chem. 2021, 17, 485–493, doi:10.3762/bjoc.17.42

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  • isoquinolines was achieved from readily available N-oxides and N-sulfonyl-1,2,3-triazoles. A variety of α-triazolylquinoline derivatives were synthesized with good regioselectivity and in excellent yields under mild reaction conditions. Further, a gram-scale and one-pot synthesis illustrated the efficacy and
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Published 17 Feb 2021

Recent developments in enantioselective photocatalysis

  • Callum Prentice,
  • James Morrisson,
  • Andrew D. Smith and
  • Eli Zysman-Colman

Beilstein J. Org. Chem. 2020, 16, 2363–2441, doi:10.3762/bjoc.16.197

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Published 29 Sep 2020

Recent synthesis of thietanes

  • Jiaxi Xu

Beilstein J. Org. Chem. 2020, 16, 1357–1410, doi:10.3762/bjoc.16.116

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  • tetrahydrotrimethyldithioxo and [3-oxo-1-thioxo or 1-oxo-3-thioxo]isoquinolines 306 and 307 with olefins 215a,b, and 186c or indene (198), the regioselective [2 + 2] cycloaddition occurred to give oxo- or thiooxospiro[isoquinoline-1,2'(or 3,2')-thietane] derivatives 208–310. In some cases, the products were accompanied with
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Published 22 Jun 2020

Oxime radicals: generation, properties and application in organic synthesis

  • Igor B. Krylov,
  • Stanislav A. Paveliev,
  • Alexander S. Budnikov and
  • Alexander O. Terent’ev

Beilstein J. Org. Chem. 2020, 16, 1234–1276, doi:10.3762/bjoc.16.107

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  • involving an isonitrile group is the reaction of β,γ-unsaturated oximes 119 with vinyl isocyanides 120 to form substituted isoquinolines 121 (Scheme 39) [129]. Both α,α-disubstituted aromatic oximes (products 121a,b,e–h) and unsubstituted (R2 = R3 = H, products 121c,d) undergo the reaction successfully. The
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Published 05 Jun 2020

Synthesis of pyrrolidinedione-fused hexahydropyrrolo[2,1-a]isoquinolines via three-component [3 + 2] cycloaddition followed by one-pot N-allylation and intramolecular Heck reactions

  • Xiaoming Ma,
  • Suzhi Meng,
  • Xiaofeng Zhang,
  • Qiang Zhang,
  • Shenghu Yan,
  • Yue Zhang and
  • Wei Zhang

Beilstein J. Org. Chem. 2020, 16, 1225–1233, doi:10.3762/bjoc.16.106

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  • ]isoquinolines. The multicomponent reaction was combined with one-pot reactions to make a synthetic method with good pot, atom and step economy. MeCN was used as a preferable green solvent for the reactions. Keywords: [3 + 2] cycloaddition; Heck reaction; hexahydropyrrolo[2,1-a]isoquinoline; one-pot reactions
  • ]isoquinolines and related ring systems [11][12][13][14][15], while medicinal chemists have also been interested in making related compounds for biological screening and drug development [16][17]. Multicomponent reactions (MCRs) have been developed as highly efficient tools for assembling heterocyclic scaffolds
  • synthesis of hexahydropyrrolo[2,1-a]isoquinolines by employing stable 1,3-dilpolar compounds generated from amino esters [15][40] or isoquinolines [41][42][43][44][45][46][47][48][49]. We like to report in this paper our effort on the synthesis of pyrrolidinedione-fused hexahydropyrrolo[2,1-a]isoquinolines
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Published 04 Jun 2020

Photocatalytic deaminative benzylation and alkylation of tetrahydroisoquinolines with N-alkylpyrydinium salts

  • David Schönbauer,
  • Carlo Sambiagio,
  • Timothy Noël and
  • Michael Schnürch

Beilstein J. Org. Chem. 2020, 16, 809–817, doi:10.3762/bjoc.16.74

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  • borylations [41][42], heteroarylations [43], and thioesterifications [44]. Additionally, several methods using photoredox chemistry were also published. For instance, the alkylation of isoquinolines under iridium catalysis and alkynylation with eosin Y as the catalyst [45][46]. In this contribution, we
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Published 21 Apr 2020

Functionalization of 4-bromobenzo[c][2,7]naphthyridine via regioselective direct ring metalation. A novel approach to analogues of pyridoacridine alkaloids

  • Benedikt C. Melzer,
  • Alois Plodek and
  • Franz Bracher

Beilstein J. Org. Chem. 2019, 15, 2304–2310, doi:10.3762/bjoc.15.222

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  • Knochel’s [19][20] and our group [21][22][23] on direct metalation of substituted isoquinolines at C-1 and in continuation of our recent work on the synthesis of aromatic oxoaporphine, oxoisoaporphine and pyridoacridine alkaloids [17][18][21][22] using direct ring metalations of heterocycles with the
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Published 26 Sep 2019

Reactions of 2-carbonyl- and 2-hydroxy(or methoxy)alkyl-substituted benzimidazoles with arenes in the superacid CF3SO3H. NMR and DFT studies of dicationic electrophilic species

  • Dmitry S. Ryabukhin,
  • Alexey N. Turdakov,
  • Natalia S. Soldatova,
  • Mikhail O. Kompanets,
  • Alexander Yu. Ivanov,
  • Irina A. Boyarskaya and
  • Aleksander V. Vasilyev

Beilstein J. Org. Chem. 2019, 15, 1962–1973, doi:10.3762/bjoc.15.191

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  • reaction [14]. Recently, several hydroxyalkylation reactions followed by alkylation of arenes have been reported involving heterocycle-based superelectrophiles: pyridines, thiazoles, quinolines, isoquinolines, pyrazines, pyrazoles, imidazole and furans, bearing a formyl (carbonyl) group [15][16][17][18][19
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Published 19 Aug 2019

Recent advances on the transition-metal-catalyzed synthesis of imidazopyridines: an updated coverage

  • Gagandeep Kour Reen,
  • Ashok Kumar and
  • Pratibha Sharma

Beilstein J. Org. Chem. 2019, 15, 1612–1704, doi:10.3762/bjoc.15.165

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Published 19 Jul 2019

Synthesis of ([1,2,4]triazolo[4,3-a]pyridin-3-ylmethyl)phosphonates and their benzo derivatives via 5-exo-dig cyclization

  • Aleksandr S. Krylov,
  • Artem A. Petrosian,
  • Julia L. Piterskaya,
  • Nataly I. Svintsitskaya and
  • Albina V. Dogadina

Beilstein J. Org. Chem. 2019, 15, 1563–1568, doi:10.3762/bjoc.15.159

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  • ]triazolo[4,3-a]pyridines was accessed through a 5-exo-dig-type cyclization of chloroethynylphosphonates and commercially available N-unsubstituted 2-hydrazinylpyridines. In addition, 3-methylphosphonylated [1,2,4]triazolo[4,3-a]quinolines and 1-methylphosphonylated [1,2,4]triazolo[3,4-a]isoquinolines were
  • ]triazolo[4,3-a]quinolines 13 and [1,2,4]triazolo[3,4-a]isoquinolines 14, respectively (Scheme 5). In the 31P NMR spectra the chemical shifts of the phosphorus nuclei in 13 and 14 are observed in the 18.40–22.75 ppm region. The 1H NMR spectra contain characteristic doublet signals of the methylene group in
  • ). Conclusion In conclusion, a series of new 3-methylphosphonylated [1,2,4]triazolo[4,3-a]pyridines, [1,2,4]triazolo[3,4-a]isoquinolines and 1-methylphosphonylated [1,2,4]triazolo[4,3-a]quinolines were synthesized through a catalyst-free 5-exo-dig-type cyclization of chloroethynylphosphonates and commercially
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Published 12 Jul 2019

Hoveyda–Grubbs catalysts with an N→Ru coordinate bond in a six-membered ring. Synthesis of stable, industrially scalable, highly efficient ruthenium metathesis catalysts and 2-vinylbenzylamine ligands as their precursors

  • Kirill B. Polyanskii,
  • Kseniia A. Alekseeva,
  • Pavel V. Raspertov,
  • Pavel A. Kumandin,
  • Eugeniya V. Nikitina,
  • Atash V. Gurbanov and
  • Fedor I. Zubkov

Beilstein J. Org. Chem. 2019, 15, 769–779, doi:10.3762/bjoc.15.73

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  • isoquinolines (Scheme 1) involved the following steps: alkylation of isoquinolines to afford isoquinolinium salts 1, its reduction with formic acid giving rise to tetrahydroisoquinolines 2 in a nearly quantitative yield, which upon alkylation gave quaternary salts 3, finally these salts underwent the Hofmann
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Published 22 Mar 2019

Electrochemically modified Corey–Fuchs reaction for the synthesis of arylalkynes. The case of 2-(2,2-dibromovinyl)naphthalene

  • Fabiana Pandolfi,
  • Isabella Chiarotto and
  • Marta Feroci

Beilstein J. Org. Chem. 2018, 14, 891–899, doi:10.3762/bjoc.14.76

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  • confirm the present interest in the chemistry of terminal alkynes, e.g., in the synthesis of sulfinamides and isothiazoles [4], 1,3-enynes [5], α-monosubstituted propargylamines [6], 2-substituted pyrazolo[5,1-a]isoquinolines [7], etc. Terminal alkynes can be prepared by dehydrohalogenation of vicinal
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Published 23 Apr 2018
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