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

• ). Accordingly, 100% F2 (1 equiv) and BF3 (1 equiv) gas were condensed into a stainless steel autoclave cooled at −196 °C, which contained cyanuric chloride (32-1, 1 equiv) in CFCl3. This was followed

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

• a multistep synthesis route. A first approach relied on the nucleophilic substitution of chlorine in cyanuric chloride with Grignard reagents, ammonia or amines [25][26], which suffered from the high reactivity of the Grignard reagents that prevents further functionalization. Moreover, this protocol

A systematic review on silica-, carbon-, and magnetic materials-supported copper species as efficient heterogeneous nanocatalysts in “click” reactions

• Pezhman Shiri and
• Jasem Aboonajmi

Beilstein J. Org. Chem. 2020, 16, 551–586, doi:10.3762/bjoc.16.52

• nanocatalyst was investigated as well. The amine-functionalized SBA-15, 19, was added to a THF solution of cyanuric chloride and DIPEA. After being stirred in a closed vessel at rt for 24 h, the produced material was filtered off and then washed with methanol, dichloromethane, and THF. The sample was again

Architecture and synthesis of P,N-heterocyclic phosphine ligands

• Wisdom A. Munzeiwa,
• Bernard Omondi and
• Vincent O. Nyamori

Beilstein J. Org. Chem. 2020, 16, 362–383, doi:10.3762/bjoc.16.35

• failed to give controlled products, i.e., when lithium phosphide was used in a 1:1 ratio a mixture of products was obtained. A reaction between one molar equivalent of cyanuric chloride (25) and tris(trimethylsilyl)phosphines formed the unstable monophosphine intermediate 26, which was isolated as amino

Azologization of serotonin 5-HT₃ receptor antagonists

• Karin Rustler,
• Galyna Maleeva,
• Piotr Bregestovski and
• Burkhard König

Beilstein J. Org. Chem. 2019, 15, 780–788, doi:10.3762/bjoc.15.74

• . Scheme 5 reflects the synthesis of the azo-extended thiomethylpurine 23 starting with the synthesis of hydroxymethylazobenzene 19 [72] in a Baeyer [62]–Mills [63] reaction and subsequent nucleophilic substitution using cyanuric chloride (20) [73] providing chloromethyl azobenzene 21. The introduction of

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

• from 4-(n-octyloxy)aniline, seven G-2 melamine-based dendrimers were obtained in 29–79% overall yields. Their iterative convergent- and chemoselective synthesis consisted of SN2-Ar aminations of cyanuric chloride and final triple N-acylations and Williamson etherifications (→ G-2 covalent trimers) or

• interested in the inclusion of 4-aminophenol, playing the role of peripheral unit, in G-0-2 dendritic melamines’ preparation, by applying the classic SN2-Ar amination of cyanuric chloride in iterative-convergent strategies. Depending on several factors such as (i) the variable π-deficiency of the s-triazine

• . To the best of our knowledge, no similar approach has been reported so far. Results and Discussion 1 Design The key elements for the construction and design of the targeted G-2 dendrimers are shown in Figure 1. Cyanuric chloride [1][2][3][4][5][6][7][8][9][10][11][12][13][14][15][16][17], 1,3,5-tris

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

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

• amide-type I and II using the same method resulted in low yields mainly because of the substitution of the methoxy group of 6 by amido anions (Supporting Information File 1). Thus, these compounds were successfully synthesized using an alternative method starting from cyanuric chloride via an

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

• 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

• 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

A macrolactonization approach to the total synthesis of the antimicrobial cyclic depsipeptide LI-F04a and diastereoisomeric analogues

• James R. Cochrane,
• Dong Hee Yoon,
• Christopher S. P. McErlean and
• Katrina A. Jolliffe

Beilstein J. Org. Chem. 2012, 8, 1344–1351, doi:10.3762/bjoc.8.154

• case of cyclization using cyanuric chloride [25]. Unfortunately, the yield could not be improved above 17% in this case, so all further reactions were performed using the Thr(O-t-Bu) protected cyclic peptides 7 and 8. With cyclic peptides 7 and 8 in hand, we chose to attach the GHPD side chain to both

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

Development of the titanium–TADDOLate-catalyzed asymmetric fluorination of β-ketoesters

• Lukas Hintermann,
• Mauro Perseghini and
• Antonio Togni

Beilstein J. Org. Chem. 2011, 7, 1421–1435, doi:10.3762/bjoc.7.166

• close to the enantioselectivity determined by GC, considering the difficulties of purifying this volatile compound on a small scale (Scheme 6). A sample of (+)-11-F of 85.6% ee (by HPLC) was treated with BCl3 and the resulting carboxylic acid esterified in situ with cyanuric chloride, N,N

• configuration to fluorination products 11-F, 10-F and 6-F. The absolute configuration of 1-F, 13-F and 12-F in relation to the sign of their optical rotation was established by Kitazume et al. [95] a) 1. BCl3, CH2Cl2, −20 °C, 15 min; 2. cyanuric chloride, PhNMe2, BnOH. b) EtOH, cat. Na, rt, 15 min. c) p-TsOH