Photoswitches beyond azobenzene: a beginner’s guide

• Michela Marcon,
• Christoph Haag and
• Burkhard König

Beilstein J. Org. Chem. 2025, 21, 1808–1853, doi:10.3762/bjoc.21.143

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

• cinnamic acid (7) in a deep eutectic solvent of choline chloride/urea (ChCl/urea) to give amides 12 and 13 in moderate yields via triacylated triazine 14 as the active ester (Scheme 5A) [36]. The TCT reagent and ChCl/urea solvent are known for their non-toxicity and low cost, promoting their wide

• ) employed N-formylpyrrolidine (FPyr) and trichlorotriazine (TCT) to catalyze the amidation of cinnamic acid derivative 121. The reaction proceeds via formation of the reactive acid chloride 36 through cascade reaction involving reactive intermediates 123 and 124 (Scheme 37) [72]. Zeng and co-workers (2019

A trustworthy mechanochemical route to isocyanides

• Francesco Basoccu,
• Federico Cuccu,
• Federico Casti,
• Rita Mocci,
• Claudia Fattuoni and
• Andrea Porcheddu

Beilstein J. Org. Chem. 2022, 18, 732–737, doi:10.3762/bjoc.18.73

• proposed. Tosyl chloride [19][20] and TCT (1,3,5-trichlorotriazine) [21] proved to be valuable alternatives to the aforementioned phosphorous compounds due to their powerful dehydrating ability. Lastly, Burgess reagent has been reported as a mild and selective dehydrating compound for formamides [22][23

Enhanced target cell specificity and uptake of lipid nanoparticles using RNA aptamers and peptides

• Roslyn M. Ray,
• Anders Højgaard Hansen,
• Maria Taskova,
• Bernhard Jandl,
• Jonas Hansen,
• Citra Soemardy,
• Kevin V. Morris and
• Kira Astakhova

Beilstein J. Org. Chem. 2021, 17, 891–907, doi:10.3762/bjoc.17.75

• ’-flouronated base; italics and underlined = 2’-O-methyl base Complementary DNA A-1: (Cy5/AGG CTA TCT AGA ATG TAC) G-3: (Cy5/TCT ATC AAT CTA TCA) Peptide synthesis, purification, and characterization Peptide assembly was carried out by solid-phase peptide synthesis in standard solid-phase extraction filtration

Synthesis, biophysical properties, and RNase H activity of 6’-difluoro[4.3.0]bicyclo-DNA

• Sibylle Frei,
• Adam K. Katolik and
• Christian J. Leumann

Beilstein J. Org. Chem. 2019, 15, 79–88, doi:10.3762/bjoc.15.9

• were the same as previously used for the 6’F-bc4,3-DNA (ON1: 5’-d(GGA TGT TCt CGA)-3’, ON2: 5’-d(GGA tGT TCT CGA)-3’, ON3: 5’-d(GGA TGt tCT CGA)-3’, ON4: 5’-d(GCA ttt ttA CCG)-3’) [37]. UV-melting experiments of the modified duplexes were recorded to assess the affinity of the 6’-diF-bc4,3-T modified

Enzyme-free genetic copying of DNA and RNA sequences

• Marilyne Sosson and
• Clemens Richert

Beilstein J. Org. Chem. 2018, 14, 603–617, doi:10.3762/bjoc.14.47

• reactivity exists. When we determined the rates for each of the different templating triplets, we found that the rate constant for extension on the poorest templating sequence (CAG) and on the best templating sequence (TCT) differed by less than two orders of magnitude, with rate constants k'CAG = 100 h−1 M

Mannich base-connected syntheses mediated by ortho-quinone methides

• Petra Barta,
• Ferenc Fülöp and
• István Szatmári

Beilstein J. Org. Chem. 2018, 14, 560–575, doi:10.3762/bjoc.14.43

• ·5PW12O40 (CuPW); [42] or wet cyanuric acid (wet-TCT) [43] was also tested. These methods suffer from a number of drawbacks, such as strong acidic media, high temperature, and prolonged reactions. Furthermore, the yields are often not satisfactory. To eliminate the disadvantages of previous strategies

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

• , TCT) as a desulfurylation reagent in the synthesis of carbodiimides or alkyl isothiocyanates from thioureas under mild conditions. Conclusion Several synthetic procedures related to thiation of heterocyclic amides have been reported to date. The drawback of the existing methods is the use of expensive

Multicomponent reactions in nucleoside chemistry

• Mariola Koszytkowska-Stawińska and
• Włodzimierz Buchowicz

Beilstein J. Org. Chem. 2014, 10, 1706–1732, doi:10.3762/bjoc.10.179

• nucleoside analogs were also prepared by these methods [101][102]. Sharma et al. used 2,4,6-trichloro[1,3,5]triazine (TCT) as the source of hydrogen chloride to promote the reactions leading to C-4-substituted C-nucleosides 81 with the high (ca. 7:1) diastereoisomeric ratio (Scheme 30) [103]. The products

• were isolated as single diastereoisomers. Since the reactions conducted in the presence of molecular sieves (4Å) were unsuccessful, the authors suggested that traces of moisture present in the reaction system played the key role in the release of hydrogen chloride from TCT. A pyranose-derived

• the previously reported Biginelli reaction [103], compounds 85 were obtained in high yields under the TCT-catalysis conditions. A pyranose-derived nucleoside analog was also prepared by this method. Using compound 87 as an example (Scheme 34), the Dondoni group demonstrated that the C-nucleosides with

Mild and efficient cyanuric chloride catalyzed Pictet–Spengler reaction

• Ashish Sharma,
• Mrityunjay Singh,
• Nitya Nand Rai and
• Devesh Sawant

Beilstein J. Org. Chem. 2013, 9, 1235–1242, doi:10.3762/bjoc.9.140

• Pictet–Spengler reaction catalyzed by cyanuric chloride (trichloro-1,3,5-triazine, TCT) is described. The 6-endo cyclization of tryptophan/tryptamine and modified Pictet–Spengler substrates with both electron-withdrawing and electron-donating aldehydes was carried out by using a catalytic amount of TCT

• (10 mol %) in DMSO under a nitrogen atmosphere. TCT catalyzed the Pictet–Spengler reaction involving electron-donating aldehydes in excellent yield. Thus, it has a distinct advantage over the existing methodologies where electron-donating aldehydes failed to undergo 6-endo cyclization. Our methodology

• provided broad substrate scope and diversity. This is indeed the first report of the use of TCT as a catalyst for the Pictet–Spengler reaction. Keywords: β-carboline; cyanuric chloride; 6-endo cyclization; Pictet–Spengler; TCT; Introduction The Pictet–Spengler reaction is an important class of name

A general and facile one-pot process of isothiocyanates from amines under aqueous conditions

• Nan Sun,
• Bin Li,
• Jianping Shao,
• Weimin Mo,
• Baoxiang Hu,
• Zhenlu Shen and
• Xinquan Hu

Beilstein J. Org. Chem. 2012, 8, 61–70, doi:10.3762/bjoc.8.6

• isothiocyanates – is still a challenge in organic chemistry. Results and Discussion Previously, Furumoto reported the application of cyanuric chloride (2,4,6-trichloro-1,3,5-triazine, TCT) as a desulfurylation reagent in the synthesis of carbodiimides from thioureas under mild conditions [60]. In that reaction

• , the S-nucleophiles first reacted with TCT and then decomposed to release the product carbodiimides and by-product 2,4,6-trimercapto-1,3,5-triazine (TMT) [61]. Considering that TCT is an efficient desulfurylation reagent of thioureas to synthesize carbodiimides and that it is affordable in large scale

• with TCT. Because inorganic bases were more efficient during the conversion of arylamines to N-aryl dithiocarbamates in aqueous systems [54][55][56][57][58][59], we chose inorganic bases to screen the optimal reaction conditions for the one-pot synthesis of 4. Following the literature procedure, N