Synthesis of new condensed naphthoquinone, pyran and pyrimidine furancarboxylates

• Kirill A. Gomonov,
• Vasilii V. Pelipko,
• Igor A. Litvinov,
• Ilya A. Pilipenko,
• Anna M. Stepanova,
• Nikolai A. Lapatin,
• Ruslan I. Baichurin and
• Sergei V. Makarenko

Beilstein J. Org. Chem. 2025, 21, 340–347, doi:10.3762/bjoc.21.24

• (2c) or 4-hydroxy-2H,5H-pyrano[3,2-c][1]benzopyran-2,5-dione (2d) in yields up to 51% (Scheme 6). Furopyrimidines 7a–f were obtained by reacting bromonitroacrylates 1a,b with representatives of substituted pyrimidines 2e–g. The reactions proceed successfully by refluxing in a water–alcohol (in the

Heteroannulations of cyanoacetamide-based MCR scaffolds utilizing formamide

• Marios Zingiridis,
• Danae Papachristodoulou,
• Despoina Menegaki,
• Konstantinos G. Froudas and
• Constantinos G. Neochoritis

Beilstein J. Org. Chem. 2025, 21, 217–225, doi:10.3762/bjoc.21.13

• of aliphatic and aromatic substituents (Scheme 4). Pyrimidines and pyrimidone-bearing indole derivatives are crucial in organic chemistry because of their extensive use as bioactive compounds with a wide array of significant biological activities (DB03074, DB03304, DB08131) [70][71][72]. In a similar

Synthesis and antimycotic activity of new derivatives of imidazo[1,2-a]pyrimidines

• Dmitriy Yu. Vandyshev,
• Daria A. Mangusheva,
• Khidmet S. Shikhaliev,
• Kirill A. Scherbakov,
• Oleg N. Burov,
• Alexander D. Zagrebaev,
• Tatiana N. Khmelevskaya,
• Alexey S. Trenin and
• Fedor I. Zubkov

Beilstein J. Org. Chem. 2024, 20, 2806–2817, doi:10.3762/bjoc.20.236

• maleimides or N-arylitaconimides. The mechanism of the studied processes was postulated basing on experimental data, HPLC–MS analysis of reaction mixtures, and quantum chemical calculations. Molecular docking results of the obtained imidazo[1,2-a]pyrimidines, when compared with voriconazole, a drug already

• compounds occupy a pivotal position in the arsenal of modern organic and medicinal chemistry due to their extensive spectrum of physiological activity [1]. Imidazo[1,2-a]pyrimidines represent one of the most promising classes of compounds within this group [2][3]. These small azoheterocyclic frameworks

• , as evidenced by the following references [11][12][13][14][15] (Figure 1). The best known method for the synthesis of imidazo[1,2-a]pyrimidines is the one developed by Chichibabin [16][17][18][19], based on the reaction between 2-aminopyrimidine and α-haloketones. Despite the widespread use of imidazo

Efficient modification of peroxydisulfate oxidation reactions of nitrogen-containing heterocycles 6-methyluracil and pyridine

• Alfiya R. Gimadieva,
• Yuliya Z. Khazimullina,
• Aigiza A. Gilimkhanova and
• Akhat G. Mustafin

Beilstein J. Org. Chem. 2024, 20, 2599–2607, doi:10.3762/bjoc.20.219

• compounds such as phenols, coumarins, pyridines, pyrimidines, quinolines, and others. This has resulted in the production of numerous valuable products. The reaction's appeal lies in its simplicity and the fact that there is no requirement to protect sensitive functional groups, thus making the introduction

Catalysing (organo-)catalysis: Trends in the application of machine learning to enantioselective organocatalysis

• Stefan P. Schmid,
• Leon Schlosser,
• Frank Glorius and
• Kjell Jorner

Beilstein J. Org. Chem. 2024, 20, 2280–2304, doi:10.3762/bjoc.20.196

• including pyrimidines and pyrazines. The importance of mechanistic understanding for model building was underlined by Kuang et al. [126], where the authors considered multi-catalyst enantioselective reactions, where one catalyst was an organocatalyst, either CPA or an amine. The co-catalyst was included in

Multicomponent syntheses of pyrazoles via (3 + 2)-cyclocondensation and (3 + 2)-cycloaddition key steps

• Ignaz Betcke,
• Alissa C. Götzinger,
• Maryna M. Kornet and
• Thomas J. J. Müller

Beilstein J. Org. Chem. 2024, 20, 2024–2077, doi:10.3762/bjoc.20.178

• pyrazole 88 (Scheme 31) [114]. In addition to pyrazoles, functionalized pyrimidines can also be prepared in a one-pot process using this method. In 2001, Bouillon et al. reported a one-pot process for synthesizing fluorinated pyrazoles. Initially, a lithium–halogen exchange was carried out on fluorinated

Negishi-coupling-enabled synthesis of α-heteroaryl-α-amino acid building blocks for DNA-encoded chemical library applications

• Matteo Gasparetto,
• Balázs Fődi and
• Gellért Sipos

Beilstein J. Org. Chem. 2024, 20, 1922–1932, doi:10.3762/bjoc.20.168

• underrepresented in the peer-reviewed literature in comparison to phenyl groups or their six-membered counterparts (e.g., pyridines, pyrimidines) [42]. Furthermore, the increasing importance of small heteroaromatic rings containing nitrogen, sulfur and/or oxygen in medicinal chemistry is well depicted by the list

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

Manganese-catalyzed C–C and C–N bond formation with alcohols via borrowing hydrogen or hydrogen auto-transfer

• Mohd Farhan Ansari,
• Atul Kumar Maurya,
• Abhishek Kumar and
• Saravanakumar Elangovan

Beilstein J. Org. Chem. 2024, 20, 1111–1166, doi:10.3762/bjoc.20.98

• the corresponding indole (98% yield) at 100 °C for 48 h [34]. One year later, Kempe and co-workers showed the multicomponent synthesis of pyrimidines from amidines and alcohols using Mn4 via C–C and C–N bond formations [94]. Various amidines were selectively coupled with different alcohols using 2 mol

• % of Mn4 and 1.1–1.5 equiv of t-BuOK in 1,4-dioxane at 120 °C for 20 h, affording good to excellent yields of the substituted pyrimidines (Scheme 68). The same group disclosed an efficient synthesis of substituted pyrroles from aminoalcohols and secondary alcohols using Mn4 under mild conditions [95

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

• structure and reactivity of the obtained macrocycle are outlined. Keywords: amidrazones; hexaazamacrocycles; pyrazolo[3,4-d]pyrimidines; ring contraction; self-assembly; Introduction The chemistry of polyazamacrocycles (PAMs) is currently one of the most rapidly developing areas of heterocyclic chemistry

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

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

• method for the synthesis of pyrimidines containing an allomaltol unit. The suggested approach is based on the reaction of 2-(1-(dimethylamino)-3-oxo-3-arylprop-1-en-2-yl)-3-hydroxy-6-methyl-4H-pyran-4-ones with cyanamide. The photochemical behavior of the obtained pyrimidines was investigated. It was

• [h]pyrano[2,3-f]quinazolines were confirmed by X-ray diffraction analysis. Based on the performed studies, a two-stage telescopic method for the synthesis of polyaromatic benzo[h]pyrano[2,3-f]quinazolines including the initial photocyclization of the starting pyrimidines and the final dehydration was

• proposed. Keywords: allomaltol; dihydrobenzo[h]pyrano[2,3-f]quinazolines; 6π-electrocyclization; photocyclization; pyrimidines; Introduction Photochemical processes involve absorption of UV light leading to the generation of molecules in the excited state and subsequent chemical transformations [1][2

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

• Scholl reaction conditions (DDQ, H+; or FeCl3, CH3NO2), the aza-[5]helicenes 22 and 24 were obtained respectively with 60% and 23% yields [38]. It was noted that with the installation of two adjacent pyrimidines in this hexarylbenzene precursor, a fully cyclized planar NG was formed toward Scholl

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

• pyrrolopyrimidines) are N-heterocycles that have become an indispensable part of research in medicinal chemistry [1][2][3]. Especially, derivatives of 3-deazaguanine (imidazo[4,5-c]pyridines) [4], 7-deazaguanine/-hypoxanthine (pyrrolo[2,3-d]pyrimidines) [5][6], and 9-deazaguanine/-hypoxanthine (pyrrolo[3,2-d

• ]-pyrimidines) [7][8][9] have been in the center of attention and were found to be effective compounds for the inhibition of various molecular targets associated with dysfunction of the central nervous system (e.g., as GABA and serotonin receptor modulators, or as inhibitors of phosphodiesterase PDE10A

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

• procedures for preparing N-ferocenoylated pyrimidines were tested earlier [19][23], and the reaction of nucleobase with (chlorocarbonyl)ferrocene (or ferrocenoyl chloride, FcCOCl) under basic conditions appeared as a simple and optimal method for the synthesis [24]. Herewith, we demonstrate that substituents

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

• interact with all HDAC isoforms of groups I, II, and IV. Thus, efforts are currently underway to synthesize inhibitors selective for certain HDAC isoforms [2]. On the other hand, pyrimidines represent an important group of heterocyclic compounds exhibiting a broad spectrum of biological activity [16][17

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

• [carbazole-2,3'-indolines], spiro[carbazole-3,5'-pyrimidines] and spiro[carbazole-3,1'-cycloalkanes] in satisfactory yields and with high diastereoselectivity. Keywords: Diels–Alder reaction; indole; indolo-2,3-quinodimethane; Levy reaction; tetrahydrocarbazole; spirooxindole; Introduction

• compound 3a (CCDC 2109578) and 4e (CCDC 2109579) were successfully determined by X-ray diffraction. It is pleased to find that the obtained spiro[carbazole-3,5'-pyrimidines] 4a–h have same cis-configuration to that of the above prepared spiro[carbazole-3,3'-indolines] 1a–j and spiro[carbazole-2,3

• sustainable, general and practical, which providing facile access to important polysubstituted spiro[carbazole-3,3'-indolines], spiro[carbazole-2,3'-indolines], spiro[carbazole-3,5'-pyrimidines] and spiro[carbazole-3,1'-cycloalkanes] with good yields and high diastereoselectivity. This reaction actually

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

• . pyrido[1,2-a]pyrrolo[3,4-d]pyrimidines 3a,b and N-methyl-4-((pyridin-2-yl)amino)maleimides 4a–e, were selectively prepared by a one-pot reaction between a functionalized maleimide and 2-aminopyridines with electron-donating or electron-withdrawing groups at position 5 and were investigated

• heterocyclic compounds, such as ring-fused pyridines (pyrido[1,2-a]pyrrolo[3,4-d]pyrimidines) and secondary aminopyridines (N-methyl-4-((pyridin-2-yl)amino)-substituted maleimides), by changing the substituents at position 5 of the 2-aminopyridine. Interestingly, among these pyridine derivatives, secondary

• aminopyridines based on the acceptor–donor–acceptor (A–D–A) system exhibit AIEE properties in aqueous media, which may be novel candidate molecules for AIEE. Herein, we report the synthesis, photophysical properties, and computational studies of pyrido[1,2-a]pyrrolo[3,4-d]pyrimidines and N-methyl-4-((pyridin-2

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

• achieving efficient deep-blue emission, we were interested to study the influence of substituents in position 2 of the pyrimidine ring on the TADF properties of pyrimidine–carbazole emitters. For this purpose, we performed the synthesis of novel 4,6-bis(3,6-di-tert-butyl-9H-carbazol-9-yl)pyrimidines

• (I) 3-methylsalicylate (CuMeSal), and Cs2CO3 as a catalyst system furnished the corresponding 2-substituted pyrimidines 2a–d. For the introduction of cyano and 4-(tert-butyl)phenylthio groups into position 2 of the pyrimidine, the conversion of the methylthio group to the better leaving

• from 0.34–0.49, was estimated for compounds with CN, SCH3, and SO2CH3 functional groups at the position 2 of the pyrimidine unit. We believe that our findings on the TADF properties of differently substituted carbazole–pyrimidines will be useful for molecular design of high-performance TADF emitters in

Synthesis of novel [1,2,4]triazolo[1,5-b][1,2,4,5]tetrazines and investigation of their fungistatic activity

• Anna V. Korotina,
• Svetlana G. Tolshchina,
• Rashida I. Ishmetova,
• Natalya P. Evstigneeva,
• Natalya A. Gerasimova,
• Natalya V. Zilberberg,
• Nikolay V. Kungurov,
• Gennady L. Rusinov,
• Oleg N. Chupakhin and
• Valery N. Charushin

Beilstein J. Org. Chem. 2022, 18, 243–250, doi:10.3762/bjoc.18.29

• particular, imidazo[1,2-a]pyridines and imidazo[1,2-a]pyrimidines exhibit a wide spectrum of biological activity, including antiviral and antibacterial ones [1][2]. A promising approach for the development of new drugs is the synthesis and bioscreening of high nitrogen-containing azoloazines, including azolo

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

• of various nucleobase derivatives, oxathiolane acetate 20a was further condensed with various pyrimidines (Scheme 34) and purines (Scheme 35), as reported by Jeong et al. [73]. When X = F, the cytosine derivative 87, among all of these nucleosides having anti-HIV activity, was found to be the most

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

• ]pyrimidines starting from readily accessible N2-pivaloyl-protected 6-chloro-7-cyano-7-deazaguanine. Substitution of the 6-chloro atom with the alcoholate of interest proceeds straightforward. The transformation of the 7-cyano substituent into the required aminomethyl group turned out to be challenging and was

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

• monomer has been used [27]. The reactivity of the above-mentioned chemical groups has enabled the attachment of various amine-functionalized groups onto the 5-position of pyrimidines via both the modified monomeric building blocks and post-synthetic ON chemistry [27][28][31][32][33][34][35][36][37][38][39

Chemical approaches to discover the full potential of peptide nucleic acids in biomedical applications

• Nikita Brodyagin,
• Martins Katkevics,
• Venubabu Kotikam,
• Christopher A. Ryan and
• Eriks Rozners

Beilstein J. Org. Chem. 2021, 17, 1641–1688, doi:10.3762/bjoc.17.116

• suggesting that Io4 may be a promising alternative to T where stronger binding is desired [108]. PNA nucleobases for Hoogsteen recognition of pyrimidines: Triple helix formation, especially using tailored oligonucleotide analogues as PNA, could be a general and sequence specific approach for molecular

• recognition of pyrimidines in hypothetical X•T–A or X•C–G triplets is complicated by two problems: 1) pyrimidines present only one hydrogen bond acceptor (C=O in T or U) or donor (-NH2 in C) in the major groove, and 2) the six-membered pyrimidine ring extends further out in the major groove than the five

• -membered ring of purines causing a steric clash with the incoming third nucleobase. In other words, the Hoogsteen face of Watson–Crick base pairs in the major groove is not isomorphous providing more space and better hydrogen bonding options for purines than for pyrimidines. Despite significant efforts by

Synthesis of functionalized imidazo[4,5-e]thiazolo[3,2-b]triazines by condensation of imidazo[4,5-e]triazinethiones with DMAD or DEAD and rearrangement to imidazo[4,5-e]thiazolo[2,3-c]triazines

• Alexei N. Izmest’ev,
• Dmitry B. Vinogradov,
• Natalya G. Kolotyrkina,
• Angelina N. Kravchenko and
• Galina A. Gazieva

Beilstein J. Org. Chem. 2021, 17, 1141–1148, doi:10.3762/bjoc.17.87

• ], antituberculosis [2], anti-inflammatory [3][4], anticancer [5], antidiabetic [6][7], and antiviral activities [8]. A significant number of biologically active thiazolidines amount to their heteroannelated derivatives, namely, condensed thiazolo[3,2-a]pyrimidines [9] and thiazolo[3,2-b]-1,2,4-triazoles [10], as