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Search for "pyrimidine" in Full Text gives 181 result(s) in Beilstein Journal of Organic Chemistry.

Switchable molecular tweezers: design and applications

  • Pablo Msellem,
  • Maksym Dekthiarenko,
  • Nihal Hadj Seyd and
  • Guillaume Vives

Beilstein J. Org. Chem. 2024, 20, 504–539, doi:10.3762/bjoc.20.45

Graphical Abstract
  • conformational switching is di(hydroxyphenyl)pyrimidine which was developed by Osakada et al. [25] (Figure 5). By default, this moiety adopts a U-shaped conformation stabilized by OH···N hydrogen bonds. In this conformation, tweezers 4 with two 9-ethynylanthryl arms form a 1:1 complex with 2,4,7
  • -trinitrofluorenone (TNF) with a good association constant of 2100 M−1. Upon protonation of the pyrimidine nitrogen atom the hydrogen bond is disturbed, which should result in a conformational change to an open W-shaped form. Even though an acid-mediated hydrogen bond disruption was expected, no clear experimental
  • that binds to the OH groups instead of the pyrimidine nitrogen atoms. The group of Aprahamian has developed hydrazone-based molecular switches that can be controlled by photochemical or chemical stimuli such as pH [27]. They reported mesogenic tweezers-like compound 5 composed of a hydrazone switch
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Published 01 Mar 2024

Cycloaddition reactions of heterocyclic azides with 2-cyanoacetamidines as a new route to C,N-diheteroarylcarbamidines

  • Pavel S. Silaichev,
  • Tetyana V. Beryozkina,
  • Vsevolod V. Melekhin,
  • Valeriy O. Filimonov,
  • Andrey N. Maslivets,
  • Vladimir G. Ilkin,
  • Wim Dehaen and
  • Vasiliy A. Bakulev

Beilstein J. Org. Chem. 2024, 20, 17–24, doi:10.3762/bjoc.20.3

Graphical Abstract
  • ] (Scheme 1A). A few years ago, we discovered that the replacement of enamines with 2-cyano-N,N-dialkylethanethioamides in this reaction [15] led to the formation of amidines containing two heterocycles: pyrimidine-2,4-dione and 1,2,3-thiadiazole (Scheme 1B). The idea came to our mind to construct a system
  • comprising pyrimidine and 1,2,3-triazole rings connected with an amidine linker by the cycloaddition reaction of 3,3-diaminoacrylonitriles with 6-azidopyrimidine (Scheme 1C). Based on this idea, an efficient and novel method with wide scope has been developed which was then applied to obtain a variety of
  • optimized reaction conditions to obtain the desired 5-amino-1,2,3-triazole-4-N-heteroarylcarbimidamides 3. In this way, 21 pyrimidine (3a–k), azolyl (3l–s), and chromenone (3t and 3u) derivatives were successfully prepared (Scheme 2 and Supporting Information File 1). Generally, the reaction proceeded in
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Published 05 Jan 2024

Unprecedented synthesis of a 14-membered hexaazamacrocycle

  • Anastasia A. Fesenko and
  • Anatoly D. Shutalev

Beilstein J. Org. Chem. 2023, 19, 1728–1740, doi:10.3762/bjoc.19.126

Graphical Abstract
  • the most electrophilic C2 carbon of the pyrimidine ring in 8 to give intermediate A. Cleavage of the C2–N3 bond in the latter followed by proton transfer in the formed zwitterion B affords bis-amidrazone C. Next, two molecules of bis-amidrazone C react with each other forming adduct D, which either
  • to 1D and 2D NMR, and HRMS (ESI+) data, the product obtained was triazolo[1,5-c]pyrimidine 13 instead of the expected macrocycle 11. The structure 13 was unambiguously confirmed by its synthesis directly from pyrazolopyrimidine 8 (ethyl orthoformate, 1.3 equiv of HCOOH, reflux, 15 h). Analogously, no
  • calculations was proposed. It involves nucleophilic attack of hydrazine on the C2 carbon of the pyrimidine ring followed by cleavage of the C2–N3 bond, dimerization of the bis-amidrazone formed, and macrocyclization of the dimer. The DFT calculations also showed that the hydrazine-promoted transformation of
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Published 15 Nov 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

Graphical Abstract
  • -Tribromopyrimidine (6a), whose core pyrimidine structure can be found in many biologically active compounds, could be sequentially substituted with 1,3,5-trimethoxybenzene and N-methylpyrrole to give 8a. The protocol also enabled the selective reductive dehalogenation at the benzylic position of 9a with green light
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Published 28 Jul 2023

Synthesis of substituted 8H-benzo[h]pyrano[2,3-f]quinazolin-8-ones via photochemical 6π-electrocyclization of pyrimidines containing an allomaltol fragment

  • Constantine V. Milyutin,
  • Andrey N. Komogortsev,
  • Boris V. Lichitsky,
  • Mikhail E. Minyaev and
  • Valeriya G. Melekhina

Beilstein J. Org. Chem. 2023, 19, 778–788, doi:10.3762/bjoc.19.58

Graphical Abstract
  • systems with a pyrimidine-bridge fragment has been described in the literature [26][27][28]. Herein, we show that for pyrimidines 9 and 10 containing an allomaltol fragment the main direction of a phototransformation is also the cyclization of the triene system. In this case, condensed dihydropyranone
  • and involves the condensation of 3-(dimethylamino)-1-phenylprop-2-en-1-one with cyanamide (14) in NMP in the presence of N-methylmorpholine [29]. However, this reaction led to a mixture of products and the yield of the target pyrimidine did not exceed 10%. It was assumed that the reported conditions
  • of the process, as well as basic reagents and solvents to identify the optimal conditions and the best results are summarized in Table 1. At first, based on literature data we carried out the reaction in NMP at 100 °C for 16 h in the presence of N-methylmorpholine. In this case the target pyrimidine
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Published 07 Jun 2023

Construction of hexabenzocoronene-based chiral nanographenes

  • Ranran Li,
  • Di Wang,
  • Shengtao Li and
  • Peng An

Beilstein J. Org. Chem. 2023, 19, 736–751, doi:10.3762/bjoc.19.54

Graphical Abstract
  • structure 13 [37]. Draper’s group reported the pyrimidine-containing N-doped NGs (Scheme 3). Tri-pyrimidine precursors 21 and 23 were obtained by trimerization of 5-(phenylethynyl)pyrimidine in the presence of Co2(CO)8. Upon treatment of the tri-pyrimidine containing hexarylbenzene compounds 21 or 23 under
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Published 30 May 2023

Synthesis of imidazo[1,2-a]pyridine-containing peptidomimetics by tandem of Groebke–Blackburn–Bienaymé and Ugi reactions

  • Oleksandr V. Kolomiiets,
  • Alexander V. Tsygankov,
  • Maryna N. Kornet,
  • Aleksander A. Brazhko,
  • Vladimir I. Musatov and
  • Valentyn A. Chebanov

Beilstein J. Org. Chem. 2023, 19, 727–735, doi:10.3762/bjoc.19.53

Graphical Abstract
  • carbonyl component was proposed, but these aldehydes did not have the structure of imidazo[1,2-a]pyridine. Interestingly, in 2019 [1], the synthesis of the amine component using GBB-3CR and the modification of the imidazo-pyrimidine scaffold by a peptidomimetic chain was carried out using the Ugi reaction
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Published 26 May 2023

Synthesis of medium and large phostams, phostones, and phostines

  • Jiaxi Xu

Beilstein J. Org. Chem. 2023, 19, 687–699, doi:10.3762/bjoc.19.50

Graphical Abstract
  • ][1,2]oxaphosphocine 2-oxides 18 in good to excellent yields in DCM at room temperature for 4–8 h in the presence of the Grubbs 1st generation catalyst. Two naphthylene-fused (19 and 20), pyrimidine-2,4(1H,3H)-dione-fused (21), and 2H-chromen-2-one-fused (22) 1,2-oxaphosphocine 2-oxides were also
  • refluxing acetonitrile for 6 h. It underwent a radical cyclization in refluxing benzene for 20 h to give rise to a nine-membered phostone thieno[2,3-d]pyrimidine-fused 2-hydroxy-1,2-oxaphosphonane 2-oxide 46 as a potential inhibitor after the deprotection of the benzyl group in the presence of DABCO in
  • from 3-bromobut-3-en-1-yl ethenyl(phenyl)phosphinate and 2-bromophenylmethyl alk-1-enylphosphinates. Synthesis of thieno[2,3-d]pyrimidine-fused 2-hydroxy-1,2-oxaphosphonane 2-oxide from benzyl hydrogen allylphosphonate and 4-chloro-3-(chloromethyl)-2-(4-methylphenyl)benzo[b]thiophene. Synthesis of 3
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Published 15 May 2023

Photocatalytic sequential C–H functionalization expediting acetoxymalonylation of imidazo heterocycles

  • Deepak Singh,
  • Shyamal Pramanik and
  • Soumitra Maity

Beilstein J. Org. Chem. 2023, 19, 666–673, doi:10.3762/bjoc.19.48

Graphical Abstract
  • ,t and 4x,y). Lastly, we explored a few heterocycles that resemble imidazo[1,2-a]pyridine to vindicate the generality of this method. Gratifyingly, 6-phenylimidazo[2,1-b]thiazole, 2-phenylbenzo[d]imidazo[2,1-b]thiazole, and 2-phenylimidazo[1,2-a]pyrimidine participated well under the standard
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Published 12 May 2023

Transition-metal-catalyzed C–H bond activation as a sustainable strategy for the synthesis of fluorinated molecules: an overview

  • Louis Monsigny,
  • Floriane Doche and
  • Tatiana Besset

Beilstein J. Org. Chem. 2023, 19, 448–473, doi:10.3762/bjoc.19.35

Graphical Abstract
  • % yields, respectively. This reaction proved to be compatible with the presence of an ester (8c) or a halogen (8e). Other directing groups, such as substituted pyridines (9a and 9b) and pyrimidine (9c) turned out to be also efficient in this transformation (Scheme 5, 4 examples, up to 84% yield). The same
  • ) were found to be suitable substrates leading to the corresponding products 12h and 12i in 91% and 83% yields, respectively. The use of other directing groups was also suitable for this transformation such as methyl and cyano-substituted pyridines 13a,b, pyrimidine (13c), pyrazole (13d), as well as the
  • % yield, 19a, 84% yield), substituted pyrazole derivatives (6 examples, up to 55% yield, 19b, 55% yield), pyrimidine (19c, 31% yield) as well as quinoline and isoquinoline (19d and 19e, 65% and 66% yields, respectively). In addition, the trifluoromethylthiolated benzo[h]quinoline 20f was obtained in good
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Published 17 Apr 2023

A new route for the synthesis of 1-deazaguanine and 1-deazahypoxanthine

  • Raphael Bereiter,
  • Marco Oberlechner and
  • Ronald Micura

Beilstein J. Org. Chem. 2022, 18, 1617–1624, doi:10.3762/bjoc.18.172

Graphical Abstract
  • synthesis of 1-deazaguanine and 1-deazahypoxanthine. Previously published routes toward these compounds focused on ring closure of the imidazole part of the purine system after the pyrimidine core had been functionalized, however, the drawback of this approach is the passage of rather hazardous/explosive
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Published 29 Nov 2022

Ferrocenoyl-adenines: substituent effects on regioselective acylation

  • Mateja Toma,
  • Gabrijel Zubčić,
  • Jasmina Lapić,
  • Senka Djaković,
  • Davor Šakić and
  • Valerije Vrček

Beilstein J. Org. Chem. 2022, 18, 1270–1277, doi:10.3762/bjoc.18.133

Graphical Abstract
  • ], or structural motifs in xeno nucleic acids [18]. In continuation of our work on ferrocenoyl-substituted pyrimidine nucleobases [19], we report herewith a combined theoretical and experimental work on purine series. The novelty of these compounds is the carbonyl linker which connects the
  • kinetic and thermodynamic control of the acylation reaction. Results and Discussion It was shown that the reaction between the pyrimidine anion (uracil, thymine, or 5-fluorouracil) and FcCOCl in N,N-dimethylformamide (DMF) proceeded in a full regiospecific mode [19]. In the purine series, however, the
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Published 19 Sep 2022

Synthesis and HDAC inhibitory activity of pyrimidine-based hydroxamic acids

  • Virginija Jakubkiene,
  • Gabrielius Ernis Valiulis,
  • Markus Schweipert,
  • Asta Zubriene,
  • Daumantas Matulis,
  • Franz-Josef Meyer-Almes and
  • Sigitas Tumkevicius

Beilstein J. Org. Chem. 2022, 18, 837–844, doi:10.3762/bjoc.18.84

Graphical Abstract
  • to differently substituted pyrimidine rings via a methylene group bridge of varying length as potential HDAC inhibitors is described. The target compounds were obtained by alkylation of 2-(alkylthio)pyrimidin-4(3H)-ones with ethyl 2-bromoethanoate, ethyl 4-bromobutanoate, or methyl 6-bromohexanoate
  • the corresponding hydroxamic acids. The synthesized hydroxamic acids were tested as inhibitors of the HDAC4 and HDAC8 isoforms. Among the synthesized pyrimidine-based hydroxamic acids N-hydroxy-6-[6-methyl-2-(methylthio)-5-propylpyrimidin-4-yloxy]hexanamide was found to be the most potent inhibitor of
  • both the HDAC4 and HDAC8 isoforms, with an IC50 of 16.6 µM and 1.2 µM, respectively. Keywords: alkylation; aminolysis; HDAC inhibitors; hydroxamic acid; pyrimidine; Introduction Histone deacetylases (HDACs) are a family of intracellular proteins responsible for removing acetyl groups in histones
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Published 13 Jul 2022

Post-synthesis from Lewis acid–base interaction: an alternative way to generate light and harvest triplet excitons

  • Hengjia Liu and
  • Guohua Xie

Beilstein J. Org. Chem. 2022, 18, 825–836, doi:10.3762/bjoc.18.83

Graphical Abstract
  • with the Lewis acids discussed in this review and thus lead to a significant shift of their optoelectronic properties. It has been confirmed that organic molecules containing pyrimidine, pyrazine, and indole groups display similar interactions upon the addition of Lewis acids [40][41][42]. Lewis acid
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Published 12 Jul 2022

Copper-catalyzed multicomponent reactions for the efficient synthesis of diverse spirotetrahydrocarbazoles

  • Shao-Cong Zhan,
  • Ren-Jie Fang,
  • Jing Sun and
  • Chao-Guo Yan

Beilstein J. Org. Chem. 2022, 18, 796–808, doi:10.3762/bjoc.18.80

Graphical Abstract
  • . On the other hand, the tetrahydrospiro[carbazole-3,5'-pyrimidine] 4 can be converted to aromatized spiro[carbazole-3,5'-pyrimidine] 3 through the oxidation of DDQ. In the absence of the effective dienophile, the normal Friedel–Crafts alkylation of 2-methylindole with aromatic aldehyde gives the well
  • ethyl acetate and light petroleum (v/v = 1:3–1:6) as eluent to give pure products 3a–c. 1',3'-Dimethyl-2,4-di-p-tolyl-2'H-spiro[carbazole-3,5'-pyrimidine]-2',4',6'(1'H,3'H)-trione (3a): Yellow solid, 75%, mp 190–192 °C; 1H NMR (400 MHz, CDCl3) δ 7.59 (d, J = 7.6 Hz, 1H, ArH), 7.35–7.30 (m, 4H, ArH
  • about three hours. After removing the solvent by evaporating at reduced pressure, the residue was subjected to column chromatography with ethyl acetate and light petroleum (v/v = 1:5–1:8) as eluent to give pure 4a–h. 1',3'-Dimethyl-2,4-diphenyl-1,2,4,9-tetrahydro-2'H-spiro[carbazole-3,5'-pyrimidine]-2
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Published 07 Jul 2022

Heteroleptic metallosupramolecular aggregates/complexation for supramolecular catalysis

  • Prodip Howlader and
  • Michael Schmittel

Beilstein J. Org. Chem. 2022, 18, 597–630, doi:10.3762/bjoc.18.62

Graphical Abstract
  • 83–85 (1:1) [98]. The thermal sliding speed of the biped across the deck 82 depends on the thermodynamic strength of the pyridine (or pyrimidine, methylpyridine) → ZnPor interactions of the biped’s feet with the ZnPor units. Obviously, weaker binding to ZnPor should lead to faster sliding [17]. With
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Published 27 May 2022

Syntheses of novel pyridine-based low-molecular-weight luminogens possessing aggregation-induced emission enhancement (AIEE) properties

  • Masayori Hagimori,
  • Tatsusada Yoshida,
  • Yasuhisa Nishimura,
  • Yukiko Ogawa and
  • Keitaro Tanaka

Beilstein J. Org. Chem. 2022, 18, 580–587, doi:10.3762/bjoc.18.60

Graphical Abstract
  • compound, 10-imino-2-methylpyrido[1,2-a]pyrrolo[3,4-d]pyrimidine-1,3(2H,10H)-dione (3a), in 97% yield. The chemical structure of product 3a was confirmed by 1H and 13C NMR spectroscopy (Figures S1 and S2 in Supporting Information File 1) and was obtained via the following reaction mechanism: nucleophilic
  • excitation maxima (Exmax), emission maxima (Emmax), and fluorescence quantum yields (Φ) of the molecules from fluorescence spectroscopic studies. The pyrido[1,2-a]pyrrolo[3,4-d]pyrimidine derivatives 3a,b possessing a highly complex ring-fused system emitted fluorescence at 545–546 nm and 537–538 nm in
  • geometries of each monomer are shown in Figure 5. The dihedral angles between the pyrimidine and maleimide rings, the amine linkage, were nearly zero degrees for 4a and 4e in all three solvents, adopting a highly planar structure as well as compound 3a. The HOMO and LUMO were distributed on the entire
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Published 24 May 2022

Substituent effect on TADF properties of 2-modified 4,6-bis(3,6-di-tert-butyl-9-carbazolyl)-5-methylpyrimidines

  • Irina Fiodorova,
  • Tomas Serevičius,
  • Rokas Skaisgiris,
  • Saulius Juršėnas and
  • Sigitas Tumkevicius

Beilstein J. Org. Chem. 2022, 18, 497–507, doi:10.3762/bjoc.18.52

Graphical Abstract
  • of TADF compounds through the selection of different electron-donating or accepting fragments opens great possibilities to tune the emission properties and rates. Here we present the synthesis of a series of novel pyrimidine–carbazole emitters and their photophysical characterization in view of
  • effects of substituents in the pyrimidine ring on their TADF properties. We demonstrate that electron-withdrawing substituents directly connected to the pyrimidine unit have greater impact on the lowering of the energy gap between singlet and triplet states (ΔEST) for efficient TADF as compared to those
  • attached through a phenylene bridge. A modification of the pyrimidine unit with CN, SCH3, and SO2CH3 functional groups at position 2 is shown to enhance the emission yield up to 0.5 with pronounced TADF activity. Keywords: carbazole; pyrimidine; RTP; synthesis; thermally activated delayed fluorescence
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Published 05 May 2022

Bifunctional thiourea-catalyzed asymmetric [3 + 2] annulation reactions of 2-isothiocyanato-1-indanones with barbiturate-based olefins

  • Jiang-Song Zhai and
  • Da-Ming Du

Beilstein J. Org. Chem. 2022, 18, 25–36, doi:10.3762/bjoc.18.3

Graphical Abstract
  • -isothiocyanato-1-indanones with barbiturate-based olefins have been developed to afford chiral dispiro[indene-pyrrolidine-pyrimidine]s. Through this strategy, the target products could be obtained in good to excellent yields with excellent stereoselectivities. In addition, the synthetic utility was verified
  • application value of this asymmetric domino Michael addition/cyclization reaction, a gram-scale experiment was performed under the optimized conditions. As exemplified in Scheme 4, the desired dispiro[indene-pyrrolidine-pyrimidine] 3ah could be obtained in 94% yield with excellent stereoselectivity (>20:1 dr
  • , >99% ee), which indicated this strategy shows promising prospects for mass production. Moreover, two different transformations of the product 3ah are shown to validate synthetic utility of the reaction. As demonstrated in Scheme 5, the dispiro[indene-pyrrolidine-pyrimidine] 3ah could be easily
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Published 04 Jan 2022

The PIFA-initiated oxidative cyclization of 2-(3-butenyl)quinazolin-4(3H)-ones – an efficient approach to 1-(hydroxymethyl)-2,3-dihydropyrrolo[1,2-a]quinazolin-5(1H)-ones

  • Alla I. Vaskevych,
  • Nataliia O. Savinchuk,
  • Ruslan I. Vaskevych,
  • Eduard B. Rusanov,
  • Oleksandr O. Grygorenko and
  • Mykhailo V. Vovk

Beilstein J. Org. Chem. 2021, 17, 2787–2794, doi:10.3762/bjoc.17.189

Graphical Abstract
  • literature to date. One of them is based on the construction of the central pyrimidine ring starting from ortho-disubstituted aromatic compounds 2 bearing a pyrrolidine moiety (see Scheme 1A). Examples include cyclocondensation of (2-pyrrolidin-1-yl)benzaldehyde and aniline occurring in the presence of TsOH
  • [13], as well as Ir-catalyzed intramolecular dehydrative cross-coupling of 2-(pyrrolidine-1-yl)benzamide [14]. Another approach to compounds of type 1 that relies on a cascade formation of the pyrimidine and pyrrole rings have found much wider application (see Scheme 1B). One of its variations
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Published 25 Nov 2021

Synthetic strategies toward 1,3-oxathiolane nucleoside analogues

  • Umesh P. Aher,
  • Dhananjai Srivastava,
  • Girij P. Singh and
  • Jayashree B. S

Beilstein J. Org. Chem. 2021, 17, 2680–2715, doi:10.3762/bjoc.17.182

Graphical Abstract
  • of TMSOTf for the N-glycosylation procedure afforded a racemic mixture. This could be due to the opening as well as closing of the oxathiolane ring under the reaction conditions. Optically pure β-ᴅ- and α-ᴅ-configured 1,3-oxathiolane pyrimidine and 1,3-oxathiolane purine nucleosides with natural
  • nucleoside configuration were synthesized by Jeong et al. (Scheme 32 and Scheme 33) [41][42]. The purpose of this was the investigation of the structure–activity relationships as anti-HIV-1 agents. The oxathiolane intermediate 20, produced from ᴅ-mannitol, was further condensed with a range of pyrimidine and
  • potent. The pyrimidine analogues 90 and 91 were also found to be active against HIV-1, with EC50 = 0.28 µM and 2.8 µM, respectively [33]. In 1992, Humber et al. [45] established a method for glycosylation of benzoylated oxathiolane 31 with silylated cytosine in the presence of trimethylsilyl iodide (TMSI
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Published 04 Nov 2021

Synthesis of O6-alkylated preQ1 derivatives

  • Laurin Flemmich,
  • Sarah Moreno and
  • Ronald Micura

Beilstein J. Org. Chem. 2021, 17, 2295–2301, doi:10.3762/bjoc.17.147

Graphical Abstract
  • in the biosynthetic pathway of the hypermodified tRNA nucleoside queuosine (Q) (Scheme 1) [5]. The core structure of the nucleobase is 7-aminomethyl-7-deazaguanine, a pyrrolo[2,3-d]pyrimidine also termed prequeuosine base (preQ1) [6][7]. In many bacteria, preQ1 binds to specific mRNA domains and
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Published 02 Sep 2021

(Phenylamino)pyrimidine-1,2,3-triazole derivatives as analogs of imatinib: searching for novel compounds against chronic myeloid leukemia

  • Luiz Claudio Ferreira Pimentel,
  • Lucas Villas Boas Hoelz,
  • Henayle Fernandes Canzian,
  • Frederico Silva Castelo Branco,
  • Andressa Paula de Oliveira,
  • Vinicius Rangel Campos,
  • Floriano Paes Silva Júnior,
  • Rafael Ferreira Dantas,
  • Jackson Antônio Lamounier Camargos Resende,
  • Anna Claudia Cunha,
  • Nubia Boechat and
  • Mônica Macedo Bastos

Beilstein J. Org. Chem. 2021, 17, 2260–2269, doi:10.3762/bjoc.17.144

Graphical Abstract
  • )pyrimidine-pyridine (PAPP) group as a pharmacophoric fragment, and these compounds were biologically evaluated. The synthesis of twelve new compounds was performed in three steps and assisted by microwave irradiation in a 1,3-dipolar cycloaddition to obtain 1,2,3-triazole derivatives substituted on carbon C
  • in the docking studies. Keywords: chronic myeloid leukemia; 1,3-dipolar cycloaddition; imatinib; (phenylamino)pyrimidine-pyridine; 1,2,3-triazole; Introduction Changes in tyrosine kinase proteins (TKPs), either by mutation or chromosomal translocation, can turn them into potent oncogenes
  • 1980s, has led to the identification of the (phenylamino)pyrimidine (PAP) structure [5][6]. The addition of an additional pyridine ring to PAP raised its cellular activity, producing PAPP, which, after some more chemical modifications, culminated in imatinib (IMT) [7]. PAPP has been used to develop new
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Published 01 Sep 2021

Cationic oligonucleotide derivatives and conjugates: A favorable approach for enhanced DNA and RNA targeting oligonucleotides

  • Mathias B. Danielsen and
  • Jesper Wengel

Beilstein J. Org. Chem. 2021, 17, 1828–1848, doi:10.3762/bjoc.17.125

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  • latter strategy can be divided into the conjugation of amine groups onto ONs still attached to the solid support, or onto ONs in solution after cleavage from the solid support. The C-5 position of the pyrimidine ring has in general been the most used attachment point since it is not involved in hydrogen
  • bonding and is facing the major groove upon duplex formation [27]. An illustrative approach that allowed the exploration of the 5-position of the pyrimidine ring as attachment site involved the use of 5-methoxycarbonylmethyl-2'-deoxyuridine and 5-trifluoroethoxycarbonyl-2’-deoxycytidine building blocks in
  • the ON synthesis [28][29][30]. The corresponding modified ONs could be converted in a versatile manner to oligomers carrying the desired amine-functionalized groups at the 5-position on the pyrimidine nucleobase [28][29][30]. Similarly, the more reactive 5-cyanomethoxycarbonylmethyl-2’-deoxyuridine
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Published 29 Jul 2021

Development of N-F fluorinating agents and their fluorinations: Historical perspective

  • Teruo Umemoto,
  • Yuhao Yang and
  • Gerald B. Hammond

Beilstein J. Org. Chem. 2021, 17, 1752–1813, doi:10.3762/bjoc.17.123

Graphical Abstract
  • ], electron-rich alkenes (entry 3) [65][66], alkyl sulfides (entry 4) [65][67], 1,3-dicarbonyl compounds [65][68], phosphonate esters (entry 5) [65], steroidal silyl enol ethers and enol acetates (entry 6) [65], pyrimidine bases and nucleosides (entry 7) [67][69], phenylalkynes (entry 8) [70], anthraquinones
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Published 27 Jul 2021
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