Multicomponent reactions driving the discovery and optimization of agents targeting central nervous system pathologies

• Lucía Campos-Prieto,
• Aitor García-Rey,
• Eddy Sotelo and
• Ana Mallo-Abreu

Beilstein J. Org. Chem. 2024, 20, 3151–3173, doi:10.3762/bjoc.20.261

• -carboxamide-1,4-benzodiazepin-5-ones when enantiopure (S)-(−)-α-methylbenzylamine and arylglyoxals were used. Thus, a reversal of diastereoselectivity was observed depending on the cyclization methodology employed, the reduction of a nitro group or the Staudinger/aza-Wittig on azide derivatives. This

Exfoliated black phosphorous-mediated CuAAC chemistry for organic and macromolecular synthesis under white LED and near-IR irradiation

• Azra Kocaarslan,
• Zafer Eroglu,
• Önder Metin and
• Yusuf Yagci

Beilstein J. Org. Chem. 2021, 17, 2477–2487, doi:10.3762/bjoc.17.164

• azide derivatives under both white LED and NIR light irradiation. Due to its deeper penetration of NIR light, the possibility of synthesizing different macromolecular structures such as functional polymers, cross-linked networks and block copolymer has also been demonstrated. The structural and

A recent overview on the synthesis of 1,4,5-trisubstituted 1,2,3-triazoles

• Pezhman Shiri,
• Ali Mohammad Amani and
• Thomas Mayer-Gall

Beilstein J. Org. Chem. 2021, 17, 1600–1628, doi:10.3762/bjoc.17.114

• derivatives from azidophilic substrates and different azide derivatives. A short reaction time, good to high yield of products, high diversity, high selectivity, and ease of operation were some benefits of this methodology. The enolate reactivity with azides was compared to enamines. The best conditions were

• )-1,2,3-triazoles 130. The triazole derivatives were prepared starting from 2-bromoaniline derivatives 126 that were transformed into desired 1-azido-2-bromobenzenes 127 using t-BuONO and TMSN3. Next, 2-bromophenyl azide derivatives 127 were reacted with phenylacetaldehyde (128) or alkynes 129 to afford

Synthesis and investigation of quadruplex-DNA-binding, 9-O-substituted berberine derivatives

• Jonas Becher,
• Daria V. Berdnikova,
• Heiko Ihmels and
• Christopher Stremmel

Beilstein J. Org. Chem. 2020, 16, 2795–2806, doi:10.3762/bjoc.16.230

• Na-cacodylate buffer were used to prepare analyte solutions with different ligand:DNA ratios (LDR = 0.00, 1.25, 2.50, 5.00). Synthesis General procedure (GP) [54] To a solution of the berberine azide derivatives 3a–e (1.0 molar equiv) and 9-propargyladenine (2, 1.1 molar equiv) in THF/MeCN 2:1 was

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

• of biologically active imidazo[1,2-a] pyridine derivatives [108]. Encouraged by the direct synthetic strategies for imidazo[1,2-a]pyridines (IPs), Donthiri et al. have reported an efficient Cu-catalyzed C–H functionalization of pyridines with vinyl azide derivatives [109]. Their use of vinyl azide

• that the presence of copper salt is mandatory for the formation of the fused heterocycle as its absence resulted in the formation of the enaminone only. The imines 118, generated in situ via the loss of nitrogen from azide derivatives, were found to be reactive towards 1,3-dipoles 117 to form diverse

• derivatives 29 for the synthesis of IPs was unprecedented. In this strategy, vinyl azide acts as a source of nitrogen with the liberation of N2 as a benign byproduct under aerobic and mild reaction conditions (Scheme 11). The protocol has surpassed the use of 2-AP as one of the mostly used reactants and

Synthesis of new p-tert-butylcalix[4]arene-based polyammonium triazolyl amphiphiles and their binding with nucleoside phosphates

• Vladimir A. Burilov,
• Guzaliya A. Fatikhova,
• Mariya N. Dokuchaeva,
• Ramil I. Nugmanov,
• Diana A. Mironova,
• Pavel V. Dorovatovskii,
• Victor N. Khrustalev,
• Svetlana E. Solovieva and
• Igor S. Antipin

Beilstein J. Org. Chem. 2018, 14, 1980–1993, doi:10.3762/bjoc.14.173

• instead of pyrophoric Raney nickel. Finally, a diazotization procedure with subsequent azide substitution [37][38] gave calix[4]arene azide derivatives 4 and 8. For the latter reaction a mixture of DMF/glacial acetic acid 3:1 was found to be the optimal solvent. The structures of macrocycles 4 and 8 were

Synthesis, effect of substituents on the regiochemistry and equilibrium studies of tetrazolo[1,5-a]pyrimidine/2-azidopyrimidines

• Elisandra Scapin,
• Paulo R. S. Salbego,
• Caroline R. Bender,
• Alexandre R. Meyer,
• Anderson B. Pagliari,
• Tainára Orlando,
• Geórgia C. Zimmer,
• Clarissa P. Frizzo,
• Helio G. Bonacorso,
• Nilo Zanatta and
• Marcos A. P. Martins

Beilstein J. Org. Chem. 2017, 13, 2396–2407, doi:10.3762/bjoc.13.237

• H5 and H6 aromatic hydrogens as doublets at 7.78–7.89 ppm and 8.67–8.79 ppm, respectively, where 3JH-H = 5.3 Hz characterizes the azide derivatives. The analysis of the 1H NMR data of compounds 5h,i shows the aromatic protons H5 and H6 as doublets in the region between 7.38–7.67 ppm and 8.80–8.85 ppm

Enduracididine, a rare amino acid component of peptide antibiotics: Natural products and synthesis

• Darcy J. Atkinson,
• Briar J. Naysmith,
• Daniel P. Furkert and
• Margaret A. Brimble

Beilstein J. Org. Chem. 2016, 12, 2325–2342, doi:10.3762/bjoc.12.226

• β-hydroxyenduracididine by Oberthür et al.: In 2009, Oberthür et al. reported a synthetic route to azide derivatives of β-hydroxyenduracididine [56]. The synthesis hinged on the use of azide 34 as a common intermediate to access both diastereomers. Diacetone D-glucose 35 was converted to azide 34 in

Sequential decarboxylative azide–alkyne cycloaddition and dehydrogenative coupling reactions: one-pot synthesis of polycyclic fused triazoles

• Kuppusamy Bharathimohan,
• Thanasekaran Ponpandian,
• A. Jafar Ahamed and
• Nattamai Bhuvanesh

Beilstein J. Org. Chem. 2014, 10, 3031–3037, doi:10.3762/bjoc.10.321

• of our knowledge, until now there have been no reports describing the combination of decarboxylative CuAAC reaction and C–H activation in an one-pot fashion. This strategy describes the preparation of fused triazoles by one-pot reaction of 2-alkynoic acid and azide derivatives. Results and Discussion

• reaction conditions. The azide derivatives 1a, 1b and 1c were prepared from 1-fluoro-2-nitrobenzene (Scheme 3) according to literature procedure [49]. Using the optimized reaction conditions, the reactivity of different 2-alkynoic acids was investigated with 1a and 1b and the results are shown in Scheme 4

Synthesis, characterization and DNA interaction studies of new triptycene derivatives

• Sourav Chakraborty,
• Snehasish Mondal,
• Rina Kumari,
• Sourav Bhowmick,
• Prolay Das and
• Neeladri Das

Beilstein J. Org. Chem. 2014, 10, 1290–1298, doi:10.3762/bjoc.10.130

• ppm in 13C NMR spectra correspond to ethynyl carbons of 1 and 2 (Supporting Information File 1). The FTIR spectrum of 3 exhibits a strong absorption band at 2108 cm–1 (ν N=N=N str.). Similarly, a band at 2113 cm–1 (s, ν N=N=N str.) suggests the formation of 4. In the proton NMR spectra of the azide

• derivatives 3 and 4, peaks corresponding to the aromatic and bridge head protons of the central triptycene core show similar splitting modes but different chemical shifts when compared with that of the corresponding triaminotriptycene derivative. In addition, compounds 3 and 4 were characterized by 13C NMR

Synthesis of enantiopure sugar-decorated six-armed triptycene derivatives

• Paola Bonaccorsi,
• Maria Luisa Di Gioia,
• Antonella Leggio,
• Lucio Minuti,
• Teresa Papalia,
• Carlo Siciliano,
• Andrea Temperini and
• Anna Barattucci

Beilstein J. Org. Chem. 2013, 9, 2410–2416, doi:10.3762/bjoc.9.278

• fully characterized. Keywords: azide derivatives; click chemistry; glycoconjugates; 2-propyn-1-yl β-D-glycopyranosides; triptycene; Introduction Triptycene (1), with its three arene units fused to the bicyclo[2.2.2]octa-2,5,7-triene system appears as a paddle wheel on closer inspection (Figure 1). The

One-pot sequential synthesis of isocyanates and urea derivatives via a microwave-assisted Staudinger–aza-Wittig reaction

• Diego Carnaroglio,
• Katia Martina,
• Giovanni Palmisano,
• Andrea Penoni,
• Claudia Domini and
• Giancarlo Cravotto

Beilstein J. Org. Chem. 2013, 9, 2378–2386, doi:10.3762/bjoc.9.274

• benzyl azide derivatives were compared to secondary ones, and the compatibility of the protocol towards different functional groups was also considered. The results obtained are given in Table 3 and show the yield of urea derivatives after purification from the amine excess by using Dowex® 50WX8-200

Influence of spacer chain lengths and polar terminal groups on the mesomorphic properties of tethered 5-phenylpyrimidines

• Gundula F. Starkulla,
• Elisabeth Kapatsina,
• Angelika Baro,
• Frank Giesselmann,
• Stefan Tussetschläger,
• Martin Kaller and
• Sabine Laschat

Beilstein J. Org. Chem. 2009, 5, No. 63, doi:10.3762/bjoc.5.63

• crystallization peak at 42 °C were observed. POM investigation displayed fan-shaped and focal conic textures, as exemplified in Figure 4. XRD experiments proved the smectic phase. In contrast to the bromides 3 and chlorides 4, the hydroxy and azide derivatives 5a,b and 7b–e were non mesomorphic and showed only

Synthesis of new triazole- based trifluoromethyl scaffolds

• Michela Martinelli,
• Thierry Milcent,
• Sandrine Ongeri and
• Benoit Crousse

Beilstein J. Org. Chem. 2008, 4, No. 19, doi:10.3762/bjoc.4.19

• Michela Martinelli Thierry Milcent Sandrine Ongeri Benoit Crousse Laboratoire BioCIS-CNRS, Faculté de Pharmacie, Univ. Paris-Sud, rue J. B. Clément, F-92296 Châtenay-Malabry, France. Fax: +33 1 46 83 57 40. 10.3762/bjoc.4.19 Abstract Trifluoromethyl propargylamines react with various azide

• derivatives to afford 1,4-disubstituted 1,2,3-triazoles through a Huisgen 1,3-dipolar cycloaddition. The reaction is catalyzed by a Cu(I) species in acetonitrile, and the corresponding products are obtained in good yields. This process thus offers an entry to new trifluoromethyl peptidomimetics as interesting