A journey in bioinspired supramolecular chemistry: from molecular tweezers to small molecules that target myotonic dystrophy

• Steven C. Zimmerman

Beilstein J. Org. Chem. 2016, 12, 125–138, doi:10.3762/bjoc.12.14

• use of a melamine (2,4,6-triamino-1,3,5-triazine) unit for formation of a base-triplet, as shown in Figure 8b. Additional reports by Lehn [78] and McLaughlin [79] supported this approach and the melamine unit has more recently been used extensively by Bong [80]. So why did we once again become

• bonds, hypothetically forming base-triplet with 2,4,6-triamino-1,3,5-triazine. (c) Aromatic recognition unit tethered to intercalator in stacked and unstacked conformation. (d) Ligand 27, an inhibitor of MBNL1N sequestration. (a) CTG trinucleotide repeat expansion in DMPK gene produces expanded

Photo, thermal and chemical degradation of riboflavin

• Muhammad Ali Sheraz,
• Sadia Hafeez Kazi,
• Sofia Ahmed,
• Zubair Anwar and
• Iqbal Ahmad

Beilstein J. Org. Chem. 2014, 10, 1999–2012, doi:10.3762/bjoc.10.208

• ,N-dioctadecyl-[1,3,5]triazine-2,4,6-triamine [122], certain amino acids and indole [123][124], proteins [125] and metals such as Ag+, Ru2+ [126] to enhance the photostability of the vitamin. Quenchers: RF on the absorption of light is promoted to the excited singlet state and then to the excited

Expeditive synthesis of trithiotriazine-cored glycoclusters and inhibition of Pseudomonas aeruginosa biofilm formation

• Meriem Smadhi,
• Sophie de Bentzmann,
• Anne Imberty,
• Marc Gingras,
• Raoudha Abderrahim and
• Peter G. Goekjian

Beilstein J. Org. Chem. 2014, 10, 1981–1990, doi:10.3762/bjoc.10.206

• processes in P. aeruginosa biofilm formation. Experimental 2,4,6-tris(1-(β-D-galactopyranosyl)triazol-4-ylmethylthio)-1,3,5-triazine (1). A solution of compound 2 (22 mg, 0.073 mmol, 1 equiv), β-D-galactopyranosyl azide (59.7 mg, 0.294 mmol, 4 equiv), CuI (0.022 mmol, 4.2 mg, 0.3 equiv) and DIPEA (0.2 mL

• ), 60.4 (C-6), 24.6 (C-b); HRMS–ESI (m/z): [M + H]+ calcd for C30H43N12O15S3, 907.2170; found, 907.2127; (m/z): [M + Na]+ calcd for C30H43N12NaO15S3, 929.1980; found, 929.1947. 2,4,6-tris(1-(β-D-glucopyranosyl)triazol-4-ylmethylthio)-1,3,5-triazine (13). A solution of compound 2 (18.1 mg, 0.062 mmol, 1

• –ESI (m/z): [M + H]+ calcd for C30H43N12O15S3, 907.2132; found, 907.2127; (m/z): [M + Na]+ calcd for C30H43N12NaO15S3. 929.1943; found, 929.1947. 2,4,6-tris(1-(β-L-fucopyranosyl)triazol-4-ylmethylthio)-1,3,5-triazine (14). Compound 2 (132.9 mg, 0.458 mmol, 1 equiv), β-L-fucopyranosyl azide (345.6 mg

Investigations of thiol-modified phenol derivatives for the use in thiol–ene photopolymerizations

• Sebastian Reinelt,
• Monir Tabatabai,
• Urs Karl Fischer,
• Norbert Moszner,
• Andreas Utterodt and
• Helmut Ritter

Beilstein J. Org. Chem. 2014, 10, 1733–1740, doi:10.3762/bjoc.10.180

• suitable allyl-modified precursors and subsequent hydrolysis. Compared to PETMP better flexural strength and modulus of elasticity are achievable in thiol–ene photopolymerizations employing 1,3,5-triallyl-1,3,5-triazine-2,4,6-trione (TATATO) as the ene derivative. Especially, after storage in water, the

• photopolymerizations regarding the conversion and mechanical properties before and after water storage is investigated and compared to the widely used PETMP. Thereby, the well-established, commercially available triallyl-1,3,5-triazine-2,4,6-trione (TATATO) is utilized as the ene monomer. Results and Discussion

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

Tailoring of organic dyes with oxidoreductive compounds to obtain photocyclic radical generator systems exhibiting photocatalytic behavior

• Christian Ley,
• Julien Christmann,
• Ahmad Ibrahim,
• Luciano H. Di Stefano and
• Xavier Allonas

Beilstein J. Org. Chem. 2014, 10, 936–947, doi:10.3762/bjoc.10.92

• )benzoate (EDB) were obtained from Aldrich, 2-(4-methoxyphenyl)-4,6-bis(trichloromethyl)-1,3,5-triazine (TA) was gifts from PCAS (France). Their chemical structures are given in Scheme 1. Evolution of RB concentration as a function of irradiation time (λ = 532 nm, 9 mW·cm−3); insert: absorption spectra

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

• additional deprotection step has to be introduced. Instead, a mild and efficient catalyst that can effectively produce iminium species in situ could generate the compound of interest without adding any extra steps. We envisaged that the use of cyanuric chloride (2,4,6-trichloro-1,3,5-triazine, TCT) [38][39

Bioactive selaginellins from Selaginella tamariscina (Beauv.) Spring

• Chao Yang,
• Yutian Shao,
• Kang Li and
• Wujiong Xia

Beilstein J. Org. Chem. 2012, 8, 1884–1889, doi:10.3762/bjoc.8.217

• conducted on precoated silica gel plates GF254 (Qingdao Marine Chemical Factory). 3-(4,5-Dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT), cisplatin, and 2,4,6-tri(2-pyridyl)-1,3,5-triazine (TPTZ) were from Aladdin Reagent Co. Ltd. 2,2’-azinobis(3-ethylbenzothiazoline-6-sulfonic acid) diammonium

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

Synthesis of methylenebisamides using CC- or DCMT- activated DMSO

• Qiang Wang,
• Lili Sun,
• Yu Jiang and
• Chunbao Li

Beilstein J. Org. Chem. 2008, 4, No. 51, doi:10.3762/bjoc.4.51

• , when amides react with electrophile-activated DMSO, the yields are rather low. We have found new electrophiles, 2,4,6-trichloro[1,3,5]triazine (CC) and 2,4-dichloro-6-methoxy[1,3,5]triazine (DCMT), which activate DMSO in the presence of amides to yield methylenebisamides in good to fair yields. The

• amides can be aromatic or aliphatic. The operation is simple and the reagents are inexpensive. Keywords: amides; condensation; DMSO; methylenebisamides; 2,4,6-trichloro[1,3,5]triazine; Introduction Sulfoxides are activated by electrophiles to produce reactive sulfonium salts. These electrophiles

• on the chlorination [10] and etherification [11] of benzyl alcohols and from other references [12][13][14], we believe the reaction between 2,4,6-trichloro[1,3,5]triazine (cyanogen chloride, or CC) and DMSO produces a reactive sulfonium salt intermediate. Therefore, it was of interest to study the