Synthesis of a new water-soluble hexacarboxylated tribenzotriquinacene derivative and its competitive host–guest interaction for drug delivery

• Man-Ping Li,
• Nan Yang and
• Wen-Rong Xu

Beilstein J. Org. Chem. 2022, 18, 539–548, doi:10.3762/bjoc.18.56

• synthesized starting from the known TBTQ-based hexakis(propargyl ether) 1 [29] (Scheme 1a). Through the CuAAC reaction with ethyl azidoacetate under Cu(I) catalysis, the TBTQ-based hexakis(ethyl acetate) compound 2 was obtained in 73% yield. Subsequent hydrolysis with sodium hydroxide followed by

[3 + 2]-Cycloaddition reaction of sydnones with alkynes

• Veronika Hladíková,
• Jiří Váňa and
• Jiří Hanusek

Beilstein J. Org. Chem. 2018, 14, 1317–1348, doi:10.3762/bjoc.14.113

• regioselectivity. Keywords: alkynes; Cu(I) catalysis; [3 + 2]-cycloaddition; mechanism; regioselectivity; sydnones; Review Introduction Since Huisgen’s discovery of the [3 + 2]-cycloaddition between 3-substituted sydnones and both terminal as well as internal alkynes [1][2] many researchers have tried to utilize

• ) is observed in most cases when a terminal alkyne was used as a reactant. On the other hand, the recent discovery of Cu(I) catalysis in the sydnone–alkyne cycloaddition (CuSAC) enables regioselective formation of complementary 1,4-disubstituted or 5-halogeno-1,4-disubstituted pyrazoles under very mild

Atom-economical group-transfer reactions with hypervalent iodine compounds

• Andreas Boelke,
• Peter Finkbeiner and
• Boris J. Nachtsheim

Beilstein J. Org. Chem. 2018, 14, 1263–1280, doi:10.3762/bjoc.14.108

• respective diaryliodonium salts 1. An atom efficient S-arylation of tetraalkylthiuram disulfides 6 was developed by Dong and co-workers under Cu(I)-catalysis (Scheme 5) [28]. This reaction yields two equivalents of S-aryl dithiocarbamates 7 and 7’ in typically high yields applying only one equivalent of a

Recent applications of click chemistry for the functionalization of gold nanoparticles and their conversion to glyco-gold nanoparticles

• Vivek Poonthiyil,
• Thisbe K. Lindhorst,
• Vladimir B. Golovko and
• Antony J. Fairbanks

Beilstein J. Org. Chem. 2018, 14, 11–24, doi:10.3762/bjoc.14.2

• , and gives a mixture of 1,4- and 1,5-triazole regioisomers (Scheme 1) [39]. Interest in and applications of the AAC have surged over the past 15 or so years, since the introduction of Cu(I) catalysis, which led to significant improvements in both the regioselectivity and rates of the reaction [40][41

Cu(I)-catalyzed N,N’-diarylation of natural diamines and polyamines with aryl iodides

• Svetlana P. Panchenko,
• Alexei D. Averin,
• Maksim V. Anokhin,
• Olga A. Maloshitskaya and
• Irina P. Beletskaya

Beilstein J. Org. Chem. 2015, 11, 2297–2305, doi:10.3762/bjoc.11.250

• diamines 3 and 4 we managed to isolate N,N’-diaryl derivatives 38 and 40, though their yields were too small (10 and 18%, respectively), the main products being N-(2-fluorophenyl) diamines 39 and 41. N,N’-Diarylation of tri- and tetraamines Arylation of two primary amino groups in polyamines under Cu(I

• )-catalysis conditions is a more challenging task than N,N’-diarylation of diamines because copper-catalyzed amination is less selective than palladium-catalyzed coupling. In view of earlier obtained data we used the CuI/L1/EtCN catalytic system for the diarylation of the triamine 5 (Scheme 5, Table 4). In

Microwave-assisted Cu(I)-catalyzed, three-component synthesis of 2-(4-((1-phenyl-1H-1,2,3-triazol-4-yl)methoxy)phenyl)-1H-benzo[d]imidazoles

• Yogesh Kumar,
• Vijay Bahadur,
• Anil K. Singh,
• Virinder S. Parmar,
• Erik V. Van der Eycken and
• Brajendra K. Singh

Beilstein J. Org. Chem. 2014, 10, 1413–1420, doi:10.3762/bjoc.10.145

• : benzimidazole; Cu(I) catalysis; microwave-assisted synthesis; multicomponent; three component synthesis; Introduction Due to their structural range and biological importance nitrogen-containing heterocycles have been striking targets for many years. They are found in a variety of natural products and are

Efficient continuous-flow synthesis of novel 1,2,3-triazole-substituted β-aminocyclohexanecarboxylic acid derivatives with gram-scale production

• Sándor B. Ötvös,
• Ádám Georgiádes,
• István M. Mándity,
• Lóránd Kiss and
• Ferenc Fülöp

Beilstein J. Org. Chem. 2013, 9, 1508–1516, doi:10.3762/bjoc.9.172

• acetylenes [16]. The classical Huisgen reaction, thermally induced, gives an approximate 1:1 mixture of 1,4- and 1,5-disubstituted 1,2,3-triazole isomers (Scheme 1) [17]. However, when Cu(I) catalysis is applied, the reaction becomes regioselective, exclusively yielding the 1,4-regioisomer within a

Recent advances in direct C–H arylation: Methodology, selectivity and mechanism in oxazole series

• Cécile Verrier,
• Pierrik Lassalas,
• Laure Théveau,
• Guy Quéguiner,
• François Trécourt,
• Francis Marsais and
• Christophe Hoarau

Beilstein J. Org. Chem. 2011, 7, 1584–1601, doi:10.3762/bjoc.7.187

• rationalized route for the direct arylation of azoles, including oxazoles, by using a strong base under Cu(I) catalysis and based upon the previous formation of the oxazol-2-ylcuprate intermediate suitable in a subsequent oxidative step with aryliodide (Scheme 18, route A) [45]. However, Bellina and Rossi

• -metallated oxazole with its ring-open tautomer [67]. Using Pd(0)/Cu(I) catalysis, the C2-cuprated oxazole may act as a transmetallating agent through a standard cross-coupling reaction (Scheme 18, route B) [67]. Under Pd(0)- and Cu(I)-free catalysis, Zhuralev identified a cross-coupling-type mechanism for

Dimerization of propargyl and homopropargyl 6-azido- 6-deoxy- glycosides upon 1,3-dipolar cycloaddition

• Nikolas Pietrzik,
• Daniel Schmollinger and
• Thomas Ziegler

Beilstein J. Org. Chem. 2008, 4, No. 30, doi:10.3762/bjoc.4.30

• ' with 5 under Cu(I)-catalysis, however, only resulted in a complex mixture of reaction products from which no uniform product could be isolated. Therefore, it was concluded that 4a and 4a' may have reacted with themselves resulting in products of oligomerization. Indeed, when 4a was treated with a