Recent advances in synthetic approaches for bioactive cinnamic acid derivatives

• Betty A. Kustiana,
• Galuh Widiyarti and
• Teni Ernawati

Beilstein J. Org. Chem. 2025, 21, 1031–1086, doi:10.3762/bjoc.21.85

• could be recycled by adding POCl3 and KSCN, thus promoting the reagent’s sustainability by reducing waste. Carboxyl group activation can also be achieved by using triazine-based reagents. For example, Saberi and Salimiyan (2019) applied 2,4,6-trichloro-1,3,5-triazine (TCT) to perform amidation of

Red light excitation: illuminating photocatalysis in a new spectrum

• Lucas Fortier,
• Corentin Lefebvre and
• Norbert Hoffmann

Beilstein J. Org. Chem. 2025, 21, 296–326, doi:10.3762/bjoc.21.22

• processes. Cyanins have been shown to effectively initiate radical polymerization under visible light through mechanisms such as borate oxidation [61] and 1,3,5-triazine reduction [62]. More recently, cyanin dyes have enabled the reduction of iodonium salts under NIR excitation [63][64]. These preliminary

New triazinephosphonate dopants for Nafion proton exchange membranes (PEM)

• Fátima C. Teixeira,
• António P. S. Teixeira and
• C. M. Rangel

Beilstein J. Org. Chem. 2024, 20, 1623–1634, doi:10.3762/bjoc.20.145

• combinatorial chemistry [35], in analytical chemistry, in electrochemical redox processes, in crystal engineering, and as fluorescent, light emitting, corrosion inhibitors or several other materials [36][37][38][39][40][41][42]. The most used triazine is 1,3,5-triazine (or s-triazine) that can provide

• symmetrical monosubstituted derivatives, or di- or trisubstituted symmetrical or asymmetrical derivatives. The C3 symmetry of 1,3,5-triazine makes it a popular heterocyclic core for the synthesis of star-shaped molecules [43][44][45], which was being used to the construction of triangular molecules, including

• chlorine atoms of 2,4,6-trichloro-1,3,5-triazine (cyanuric chloride, 1) by the previously synthesized nucleophiles. The general scheme to obtain the desired triazinephosphonates (TPs) from the synthesized amino nucleophiles are represented in Scheme 5. Initially, the 4-aminophenyl derivatives were

Structure–property relationships in dicyanopyrazinoquinoxalines and their hydrogen-bonding-capable dihydropyrazinoquinoxalinedione derivatives

• Tural N. Akhmedov,
• Ajeet Kumar,
• Daken J. Starkenburg,
• Kyle J. Chesney,
• Khalil A. Abboud,
• Novruz G. Akhmedov,
• Jiangeng Xue and
• Ronald K. Castellano

Beilstein J. Org. Chem. 2024, 20, 1037–1052, doi:10.3762/bjoc.20.92

• device fabrication with the electron acceptor C60. Subsequently, the design was extended to “ditopic” systems with diverse HB-capable units such as PH, 2,4-diamino-1,3,5-triazine (DAT), and barbiturate (B) that can form trimeric and hexameric “rosettes”, respectively [16]. The Sokolowski and Głowacki

Activity assays of NnlA homologs suggest the natural product N-nitroglycine is degraded by diverse bacteria

• Kara A. Strickland,
• Brenda Martinez Rodriguez,
• Ashley A. Holland,
• Shelby Wagner,
• Michelle Luna-Alva,
• David E. Graham and
• Jonathan D. Caranto

Beilstein J. Org. Chem. 2024, 20, 830–840, doi:10.3762/bjoc.20.75

• hexahydro-1,3,5-trinitro-1,3,5-triazine (commonly called RDX), octogen (HMX), and hexanitrohexaazaisowurtzitane (CL-20) are compounds found in military grade explosives and propellants. Contamination of these cyclic nitramines in soil and groundwater is concerning due to their toxicity and potential

Study on the interactions between melamine-cored Schiff bases with cucurbit[n]urils of different sizes and its application in detecting silver ions

• Jun-Xian Gou,
• Yang Luo,
• Xi-Nan Yang,
• Wei Zhang,
• Ji-Hong Lu,
• Zhu Tao and
• Xin Xiao

Beilstein J. Org. Chem. 2021, 17, 2950–2958, doi:10.3762/bjoc.17.204

• electropositivity can be a perfect candidate for the study of outer-surface interaction of cucurbit[n]urils [21][22][23][24]. In this work, nitrogen-rich melamine is used as the center molecule to synthesize the Schiff base 2,4,6-tris(((4-(4-carboxybutyl)phenyl)methylene)amino)-1,3,5-triazine (TBT) through the

Synthetic accesses to biguanide compounds

• Oleksandr Grytsai,
• Cyril Ronco and
• Rachid Benhida

Beilstein J. Org. Chem. 2021, 17, 1001–1040, doi:10.3762/bjoc.17.82

• equivalents of the carbodiimide in the reaction with N,N’-disubstituted guanidines resulted in the formation of 1,2-dihydro-1,3,5-triazine derivatives as the main products of the cycloaddition reaction [82]. They also showed that increasing the amount of the carbodiimide to 3 equivalents led to excellent

• triazine yields in refluxing THF (Scheme 42). The mechanism of this reaction proceeds via the formation of a nonisolated triguanide intermediate, that spontaneously cyclizes to the 1,3,5-triazine derivative after elimination of the amine counterpart (Scheme 43). The authors proposed two plausible

Microwave-assisted multicomponent reactions in heterocyclic chemistry and mechanistic aspects

• Shivani Gulati,
• Stephy Elza John and
• Nagula Shankaraiah

Beilstein J. Org. Chem. 2021, 17, 819–865, doi:10.3762/bjoc.17.71

• 115, could be only obtained. The regioisomer A being less stable due to steric hindrance between the amino and the aryl group rearranges to give desired product 115. The mechanism involved in the formation of intermediate B is similar to the mechanism proposed for amino-1,3,5-triazine ring

Optical detection of di- and triphosphate anions with mixed monolayer-protected gold nanoparticles containing zinc(II)–dipicolylamine complexes

• Lena Reinke,
• Julia Bartl,
• Marcus Koch and
• Stefan Kubik

Beilstein J. Org. Chem. 2020, 16, 2687–2700, doi:10.3762/bjoc.16.219

• spectrum at 528 nm (Figure S1 in Supporting Information File 1). Further structural information was obtained by releasing the ligand molecules from the surface of NPrac-1 with iodine, adding a known amount of 2,4,6-trimethoxy-1,3,5-triazine to the solution as an internal standard, and recording an 1H NMR

Microwave-assisted efficient one-pot synthesis of N²-(tetrazol-5-yl)-6-aryl/heteroaryl-5,6-dihydro-1,3,5-triazine-2,4-diamines

• Moustafa Sherief Moustafa,
• Ramadan Ahmed Mekheimer,
• Saleh Mohammed Al-Mousawi,
• Mohamed Abd-Elmonem,
• Hesham El-Zorba,
• Afaf Mohamed Abdel Hameed,
• Tahany Mahmoud Mohamed and
• Kamal Usef Sadek

Beilstein J. Org. Chem. 2020, 16, 1706–1712, doi:10.3762/bjoc.16.142

• Chemistry, Faculty of Science, Minia University, Minia 61519, Egypt Department of Pharmacology, Faculty of Veterinary Medicine, Cairo University, Giza 12211, Egypt 10.3762/bjoc.16.142 Abstract An efficient one-pot synthesis of N2-(tetrazol-5-yl)-6-aryl/heteroaryl-1,3,5-triazine-2,4-diamine derivatives was

• developed by reacting 5-amino-1,2,3,4-tetrazole with aromatic aldehydes and cyanamide in pyridine under controlled microwave heating with high yields. X-ray crystallography confirmed the structure of the obtained products. Keywords: microwave irradiation; N2-(tetrazol-5-yl)-6-aryl/heteroaryl-1,3,5-triazine

• [2], antitumor [3], anti-HIV [4], inhibitor of Trypanosoma brucei [5], angiogenesis inhibitor [6], antiplasmodial antifolates [7], and antimicrobial [8]. Moreover, and in particular N2,6-disubstituted-1,3,5-triazine-2,4-diamines possess a wide range of chemotherapeutic activities [8][9][10][11

One-pot synthesis of 1,3,5-triazine-2,4-dithione derivatives via three-component reactions

• Gui-Feng Kang and
• Gang Zhang

Beilstein J. Org. Chem. 2020, 16, 1447–1455, doi:10.3762/bjoc.16.120

• 100050, China 10.3762/bjoc.16.120 Abstract A catalyst-free one-pot synthetic methodology was developed for the preparation of 1,3,5-triazine-2,4-dithione derivatives through three-component reactions of arylaldehydes, thiourea, and orthoformates. The procedure tolerated a diverse range of arylaldehydes

• and orthoformates and provided a rapid entry to a variety of 4-aryl-6-(alkylthio)-3,4-dihydro-1,3,5-triazine-2(1H)-thiones (29 examples). The synthetic strategy relies on the dual role of thiourea in the cyclization with the aldehydes and the alkylation via an intermediate imidate formation. The

• structures of 1,3,5-triazine-2,4-dithione derivatives were characterized by spectroscopic techniques as well as by single crystal X-ray diffraction. Keywords: aldehydes; multicomponent reactions; nitrogen heterocycles; thiourea; triazinethiones; Introduction The construction of nitrogen-containing

Synthesis and properties of quinazoline-based versatile exciplex-forming compounds

• Rasa Keruckiene,
• Simona Vekteryte,
• Ervinas Urbonas,
• Matas Guzauskas,
• Eigirdas Skuodis,
• Dmytro Volyniuk and
• Juozas V. Grazulevicius

Beilstein J. Org. Chem. 2020, 16, 1142–1153, doi:10.3762/bjoc.16.101

• of the derivatives were in the range of 5.22–5.87 eV. The 3,6-di-tert-butylcarbazole-substituted quinazoline-based compound forms a sky-blue emitting exciplex in solid mixture with the acceptor 2,4,6-tris[3-(diphenylphosphinyl)phenyl]-1,3,5-triazine as well as an orange emitting exciplex with the

• regarded as a promising candidate for blue exciplex formation in the solid state. Indeed, compound 1 formed a sky-blue emitting exciplex (501 nm) in a solid mixture with the acceptor 2,4,6-tris[3-(diphenylphosphinyl)phenyl]-1,3,5-triazine (PO-T2T). Moreover, an orange exciplex emission with a PL spectrum

• be in the range of 5.22–5.87 eV. The 3,6-di-tert-butylcarbazole-substituted quinazoline derivative formed a sky-blue emitting exciplex with the acceptor 2,4,6-tris[3-(diphenylphosphinyl)phenyl]-1,3,5-triazine as well as an orange emitting exciplex with the donor 4,4′,4″-tris[3-methylphenyl(phenyl

Synthesis, photophysical and electrochemical properties of pyridine, pyrazine and triazine-based (D–π–)₂A fluorescent dyes

• Keiichi Imato,
• Toshiaki Enoki,
• Koji Uenaka and
• Yousuke Ooyama

Beilstein J. Org. Chem. 2019, 15, 1712–1721, doi:10.3762/bjoc.15.167

• were prepared by Stille coupling of stannyl compound 1 [3] with 3,5-dibromopyridine, 2,6-diiodopyrazine, and 2,4-dichloro-1,3,5-triazine, respectively (Scheme 1; see Experimental section for the synthetic procedure of OUJ-2). Optical properties The photoabsorption and fluorescence spectra of OUY-2, OUK

• -7000 (Hokuto Denko). Synthesis General synthetic procedure of (D–π–)2A fluorescent dyes OUY-2, OUK-2 and OUJ-2 OUY-2 [2], OUK-2 [3] and OUJ-2 were prepared by Stille coupling of stannyl compound 1 [3] with 3,5-dibromopyridine, 2,6-diiodopyrazine, and 2,4-dichloro-1,3,5-triazine, respectively, by using

• Pd(PPh3)4 as a catalyst in toluene at 110 °C under an argon atmosphere (Scheme 1). Synthesis of OYJ-2: A solution of 1 [3] (0.60 g, 0.95 mmol), 2,4-dichloro-1,3,5-triazine (0.071 g, 0.48 mmol), and Pd(PPh3)4 (0.18 g, 0.16 mmol) in toluene (10 mL) was stirred for 48 h at 110 °C under an argon

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

• iron MOFs have resulted in lesser yield than Cu-MOF. The reaction has well tolerated different substituent on the reactants except for 4-NO2; 3,4-dichlorobenzaldehyde, 2-aminopyrimidine, and 2,4,6-triamino-1,3,5-triazine which failed to give the desired product. Also, benzaldehydes substituted with

Mechanochemistry of supramolecules

• Anima Bose and
• Prasenjit Mal

Beilstein J. Org. Chem. 2019, 15, 881–900, doi:10.3762/bjoc.15.86

• the formation of a Pt-based supramolecular square took more than four weeks at 100 °C. Using a similar approach, Otera’s group also demonstrated for the formation of a bowl-shaped assembly 9 in 90% yield upon grinding for 10 min 2,4,6-tri(pyridin-3-yl)-1,3,5-triazine and palladium ((en)Pd(NO3)2

A switchable [2]rotaxane with two active alkenyl groups

• Xiu-Li Zheng,
• Rong-Rong Tao,
• Rui-Rui Gu,
• Wen-Zhi Wang and
• Da-Hui Qu

Beilstein J. Org. Chem. 2018, 14, 2074–2081, doi:10.3762/bjoc.14.181

• amide reaction between compound 6 and 6-azidohexan-1-amine in the presence of 2-chloro-4,6-dimethoxy-1,3,5-triazine and N-methylmorpholine. Finally, the classical and effective “Click” reaction was used to produce the target compound [2]rotaxane R1. The crown ether 9 and dibenzylammonium ion (R2NH2

• reported. Synthesis Compound 8: The mixture of compound 6 (5.0 g, 6.83 mmol), compound 7 (2.9 g, 20.49 mmol) and 2-chloro-4,6-dimethoxy-1,3,5-triazine (CDMT, 3.6 g, 20.49 mmol) was placed in a 250 mL round-bottom flask and dissolved by 100 mL methylene chloride. Then, N-methylmorpholine (NMM, 3.5 g, 34.15

Design, synthesis and structure of novel G-2 melamine-based dendrimers incorporating 4-(n-octyloxy)aniline as a peripheral unit

• Cristina Morar,
• Pedro Lameiras,
• Attila Bende,
• Gabriel Katona,
• Emese Gál and
• Mircea Darabantu

Beilstein J. Org. Chem. 2018, 14, 1704–1722, doi:10.3762/bjoc.14.145

• to self-organise in solution and to self-assembly in the solid state. Keywords: amination; dendrimers; melamines; nano-aggregates; 4-(n-octyloxy)aniline; Introduction N-Substituted melamine (2,4,6-triamino-1,3,5-triazine)-based dendrimers are a class of macromolecules reported as early as 2000 by E

A three-armed cryptand with triazine and pyridine units: synthesis, structure and complexation with polycyclic aromatic compounds

• Claudia Lar,
• Adrian Woiczechowski-Pop,
• Attila Bende,
• Ioana Georgeta Grosu,
• Natalia Miklášová,
• Elena Bogdan,
• Niculina Daniela Hădade,
• Anamaria Terec and
• Ion Grosu

Beilstein J. Org. Chem. 2018, 14, 1370–1377, doi:10.3762/bjoc.14.115

• , Slovakia 10.3762/bjoc.14.115 Abstract The aromatic nucleophilic substitution reaction based synthesis of a three-armed cryptand displaying 2,4,6-triphenyl-1,3,5-triazine units as caps and pyridine rings in the bridges, along with NMR, MS and molecular modelling-based structural analysis of this compound

• titration; 1,3,5-triazine; Introduction Cryptands with C3-symmetric aromatic reference groups are exciting targets, on the one hand due to the challenges encountered in their synthesis and on the other due to their ability (macrobicyclic effect [1]) to form supramolecular assemblies with cations, anions or

• , 53-C), 169.87 (11-C, 15-C, 31-C, 35-C, 47-C, 51-C); MS–APCI+ (m/z): [M + H]+ 1090.3 (calcd 1090.2). Cryptands with 1,3,5-triphenylbenzene (1) and 2,4,6-triphenyl-1,3,5-triazine (2) aromatic reference groups. NMR spectra of cryptand 2: top, 1H NMR; bottom, 13C NMR. Chemical shift changes of the

Phosphodiester models for cleavage of nucleic acids

• Satu Mikkola,
• Tuomas Lönnberg and
• Harri Lönnberg

Beilstein J. Org. Chem. 2018, 14, 803–837, doi:10.3762/bjoc.14.68

• guanidinium compound. This low basicity was suggested to be a central factor behind the catalytic activity. A clarification of the mechanism of guanidine-based catalysis has more recently been attempted by anchoring a 2,4-diamino-1,3,5-triazine core to the N3 of uracil bases of UpU by two side arms, each

Recent advances on organic blue thermally activated delayed fluorescence (TADF) emitters for organic light-emitting diodes (OLEDs)

• Thanh-Tuân Bui,
• Fabrice Goubard,
• Malika Ibrahim-Ouali,
• Didier Gigmes and
• Frédéric Dumur

Beilstein J. Org. Chem. 2018, 14, 282–308, doi:10.3762/bjoc.14.18

• to combine the electron-donating 9,9-dimethyl-10-phenylacridan with the electron-accepting 2,4,6-triphenyl-1,3,5-triazine was reported under the form of random copolymers derived from a polystyrene (T31–T34, see Figure 9) [60]. Contrarily to the classical TADF materials in which the electron donor is

5-Aminopyrazole as precursor in design and synthesis of fused pyrazoloazines

• Ranjana Aggarwal and
• Suresh Kumar

Beilstein J. Org. Chem. 2018, 14, 203–242, doi:10.3762/bjoc.14.15

A novel method for heterocyclic amide–thioamide transformations

• Walid Fathalla,
• Ibrahim A. I. Ali and
• Pavel Pazdera

Beilstein J. Org. Chem. 2017, 13, 174–181, doi:10.3762/bjoc.13.20

• extra proton to II to afford the quinazoline thione C2. On the other hand the free cyclohexylamine will add to cyclohexyl isothiocyanate (4) to form the thiourea 3. Similar results were obtained by Furumoto [40], and Sun [41] reported the application of cyanuric chloride (2,4,6-trichloro-1,3,5-triazine

Elongated and substituted triazine-based tricarboxylic acid linkers for MOFs

• Arne Klinkebiel,
• Ole Beyer,
• Barbara Malawko and
• Ulrich Lüning

Beilstein J. Org. Chem. 2016, 12, 2267–2273, doi:10.3762/bjoc.12.219

• the repulsion of the ortho-hydrogen atoms in the biphenyl subunits. An exchange of the central benzene ring by a 1,3,5-triazine (1,3,5-triazine-2,4,6-tribenzoate, TATB, Figure 1, right), however, permits planarity. The respective MOF from TATB and copper is PCN-6 [8]. While the orientation of the

• (for further information see Supporting Information File 1). A detailed comparison of triarylbenzene and triaryl-1,3,5-triazine based MOFs and a discussion on the differences in sterical hindrance in benzene and 1,3,5-triazine based structures has been undertaken for tetrazol terminated linkers [9

• ” methylation [25] could find a remedy. Steric repulsion between ortho-hydrogen atoms in benzene-1,3,5-tribenzoic acid (BTB) leads to a non-planar structure (left). The exchange of CH units by nitrogen atoms in the central six-membered ring allows a planar structure: 1,3,5-triazine-2,4,6-tribenzoic acid (TATB

Potent triazine-based dehydrocondensing reagents substituted by an amido group

• Munetaka Kunishima,
• Daiki Kato,
• Nobu Kimura,
• Masanori Kitamura,
• Kohei Yamada and
• Kazuhito Hioki

Beilstein J. Org. Chem. 2016, 12, 1897–1903, doi:10.3762/bjoc.12.179

• feature enables the use of DMT-MM for dehydrocondensing reactions in water or alcohols to give amides without the recovery of hydrolyzed carboxylic acids and the formation of corresponding esters. DMT-MM is quantitatively synthesized from 2-chloro-4,6-dimethoxy-1,3,5-triazine (CDMT) and N-methylmorpholine

• intermediate in Scheme 1b, basically shows the same reactivity for aminolysis and alcoholysis regardless of which tertiary amine 5 was used (Scheme 1b,d). Therefore, it is reasonable to modify the activity of the 1,3,5-triazine ring that is involved in both steps shown in Scheme 1b by introducing another

• substituents (R3 = Me or Ph), and the methyl, phenyl, or hydrogen substituent was placed at R4. Tertiary amide-type compounds III–VI were prepared in one step from the well-known commercially available 2,4-dichloro-6-methoxy-1,3,5-triazine (6) [20] (Scheme 2). In contrast, attempts to prepare the secondary

New synthetic strategies for xanthene-dye-appended cyclodextrins

• Milo Malanga,
• Andras Darcsi,
• Mihaly Balint,
• Gabor Benkovics,
• Tamas Sohajda and
• Szabolcs Beni

Beilstein J. Org. Chem. 2016, 12, 537–548, doi:10.3762/bjoc.12.53

• formation of these byproducts could lead to depletion of the coupling agent by conversion to 2-hydroxy-4,6-dimethoxy-1,3,5-triazine (DMM-OH) and could explaining the moderate conversion of the starting material. It is worth emphasizing that the coupling of fluorescein based on DCC/HOBt in organic solvents