Effects of the aldehyde-derived ring substituent on the properties of two new bioinspired trimethoxybenzoylhydrazones: methyl vs nitro groups

• Dayanne Martins,
• Roberta Lamosa,
• Talis Uelisson da Silva,
• Carolina B. P. Ligiero,
• Sérgio de Paula Machado,
• Daphne S. Cukierman and
• Nicolás A. Rey

Beilstein J. Org. Chem. 2023, 19, 1713–1727, doi:10.3762/bjoc.19.125

• ; phenol acidity; ring substituents; XRD; Introduction N-Acylhydrazones are a class of compounds that contain the hydrazonic functional group (–NH–N=C–) attached to an acyl group, which can be modified to generate a range of different structures with varying properties [1]. The versatility of this class

Synthesis and biological evaluation of Argemone mexicana-inspired antimicrobials

• Jessica Villegas,
• Bryce C. Ball,
• Katelyn M. Shouse,
• Caleb W. VanArragon,
• Ashley N. Wasserman,
• Hannah E. Bhakta,
• Allen G. Oliver,
• Danielle A. Orozco-Nunnelly and
• Jeffrey M. Pruet

Beilstein J. Org. Chem. 2023, 19, 1511–1524, doi:10.3762/bjoc.19.108

• , chelerythrine analogs with modifications to the ring substituents can be seen as ubiquitous with sanguinarine analogs. Our group has been focused on exploring new compounds with antibacterial and antifungal properties, which may serve to ease the strain caused by the ever-growing list of drug-resistant

Aromatic C–H bond functionalization through organocatalyzed asymmetric intermolecular aza-Friedel–Crafts reaction: a recent update

• Anup Biswas

Beilstein J. Org. Chem. 2023, 19, 956–981, doi:10.3762/bjoc.19.72

• substrate scope was achieved by varying the substituents in the C3 position of the isoxazoles 82 and the carbocyclic ring substituents in ketimines 49. Few more products were added to the library by altering the substituents of the amine in 82 and the ring nitrogen in 49 (Scheme 20a) [48]. The

Recent advances in the syntheses of anthracene derivatives

• Giovanni S. Baviera and
• Paulo M. Donate

Beilstein J. Org. Chem. 2021, 17, 2028–2050, doi:10.3762/bjoc.17.131

• anthracenes, previously shown in Scheme 7 [41], the key to obtaining anthraquinones was the photooxidation induced by visible light, which afforded the substituted anthraquinones 194. In this case, the effect of the aromatic ring substituents also affected the yield of the anthraquinones, as can be seen from

Regioselective N-alkylation of the 1H-indazole scaffold; ring substituent and N-alkylating reagent effects on regioisomeric distribution

• Ryan M. Alam and
• John J. Keating

Beilstein J. Org. Chem. 2021, 17, 1939–1951, doi:10.3762/bjoc.17.127

• , solvent, and temperature.a Indazole C-3 substituent effects. Effect of NaH and THF on N-1 regioselectivity.a Effect of indazole benzenoid ring substituents on N-1:N-2 regioselectivity.a Effect of 15-crown-5 on the regioselective N-alkylation of indazole 9, in the presence of NaH in THF.a Alkylating

One-pot synthesis of dicyclopenta-fused peropyrene via a fourfold alkyne annulation

• Ji Ma,
• Yubin Fu,
• Junzhi Liu and
• Xinliang Feng

Beilstein J. Org. Chem. 2020, 16, 791–797, doi:10.3762/bjoc.16.72

• annulation was favorable for the formation of six-membered rings. Nevertheless, the existence of several rotamers of 1 derived from the restricted rotation of the peripheral phenyl ring substituents and its nonplanar geometry prevented the structure elucidation by proton NMR analysis [35]. Single crystals of

Potent hemithioindigo-based antimitotics photocontrol the microtubule cytoskeleton in cellulo

• Alexander Sailer,
• Franziska Ermer,
• Yvonne Kraus,
• Rebekkah Bingham,
• Ferdinand H. Lutter,
• Julia Ahlfeld and
• Oliver Thorn-Seshold

Beilstein J. Org. Chem. 2020, 16, 125–134, doi:10.3762/bjoc.16.14

• determinant of bioactivity), but the photoswitchability increased substantially (3-fold with regard to the lit/dark ratio). We took this as an encouraging indicator of the overall polarity required for binding, and now examined re-orienting the south ring substituents by shifting the trimethoxy pattern on the

Selective carboxylation of reactive benzylic C–H bonds by a hypervalent iodine(III)/inorganic bromide oxidation system

• Toshifumi Dohi,
• Shohei Ueda,
• Kosuke Iwasaki,
• Yusuke Tsunoda,
• Koji Morimoto and
• Yasuyuki Kita

Beilstein J. Org. Chem. 2018, 14, 1087–1094, doi:10.3762/bjoc.14.94

• acetoxylation at the activated benzyl carbon adjacent to an oxygen atom proceeded smoothly as shown by the formation of the pseudo acetal 2g (Table 2, entry 6). Diphenylmethane and its derivatives were very good substrates for our system and were less sensitive to the electronic effects of the aromatic ring

• substituents than in other previously described compounds, showing higher reactivity and chemoselectivity of the benzylic position (see ref. [51]). The reactions of substrates 1h–j proceeded without the use of zinc(II) acetate (see Table 2, entries 7–9 versus entry 2). The installation of other carboxylic

Exploring endoperoxides as a new entry for the synthesis of branched azasugars

• Svenja Domeyer,
• Mark Bjerregaard,
• Henrik Johansson and
• Daniel Sejer Pedersen

Beilstein J. Org. Chem. 2017, 13, 644–647, doi:10.3762/bjoc.13.63

• hydrolysis transition states as well as having many other interesting properties. They are found in nature as pyrrolidines, piperidines, indolizidines, pyrrolizidines or nortropane alkaloids with a variety of ring substituents, typically hydroxy groups, carboxylic acids and amides [1]. The ability of

cis–trans-Amide isomerism of the 3,4-dehydroproline residue, the ‘unpuckered’ proline

• Vladimir Kubyshkin and
• Nediljko Budisa

Beilstein J. Org. Chem. 2016, 12, 589–593, doi:10.3762/bjoc.12.57

• as the exo- and endo-puckers, as well as in twisted forms [6][7]. Various ring substituents can significantly shift the equilibrium towards a high preference for one particular conformation. For instance, 3- [8][9] and 4-ring [10][11][12][13][14][15] substituents have been characterized to shift the

Effect of cyclodextrin complexation on phenylpropanoids’ solubility and antioxidant activity

• Miriana Kfoury,
• David Landy,
• Lizette Auezova,
• Hélène Greige-Gerges and
• Sophie Fourmentin

Beilstein J. Org. Chem. 2014, 10, 2322–2331, doi:10.3762/bjoc.10.241

• efficiency (CE), PP:CD molar ratio, increase in formulation bulk and complexation energy were assessed. All complexes exhibited a 1:1 stoichiometry but their stability was influenced by the nature and the position of the phenyl ring substituents. A relationship between the intrinsic solubility of guests (S0

• maintained rigid, while the PP was freely modified. For each PP, two types of inclusion complexes according to the two docking strategies were explored (E1 and E2 which refers to the penetration of the CD cavity by the PP via the propenyl or allyl chain moiety or other phenyl ring substituents, respectively

Mechanistic studies on the CAN-mediated intramolecular cyclization of δ-aryl-β-dicarbonyl compounds

• Brian M. Casey,
• Dhandapani V. Sadasivam and
• Robert A. Flowers II

Beilstein J. Org. Chem. 2013, 9, 1472–1479, doi:10.3762/bjoc.9.167

• carboxylic acids with CAN. Proposed mechanism for the conversion of δ-aryl-β-dicarbonyl compounds to β-tetralones (path A) and methyl esters (path B). CAN-mediated oxidation of δ-aryl-β-dicarbonyl compounds in MeOHa. Impact of ring substituents on the CAN-mediated oxidation of δ-aryl-β-dicarbonyl compounds

Interplay of ortho- with spiro-cyclisation during iminyl radical closures onto arenes and heteroarenes

• Roy T. McBurney and
• John C. Walton

Beilstein J. Org. Chem. 2013, 9, 1083–1092, doi:10.3762/bjoc.9.120

• the nodal plane of their C=N π-systems [30][31][32]. This precludes substantial delocalization of the unpaired electron into the ring π-system of aryliminyls. Consequently, strong effects from ring substituents of aryliminyls are not expected to come into play. Small to moderate size iminyl radicals

Cation affinity numbers of Lewis bases

• Christoph Lindner,
• Raman Tandon,
• Boris Maryasin,
• Evgeny Larionov and
• Hendrik Zipse

Beilstein J. Org. Chem. 2012, 8, 1406–1442, doi:10.3762/bjoc.8.163

• , indicating a negligible influence of ring aromaticity. The influence of the ring substituents on MCA values is less systematic and depends on the ring system at hand. For all systems, however, the largest MCA values are obtained for mesityl substituents. Mayr and co-workers have determined nucleophilicity

Regio- and stereoselective oxidation of unactivated C–H bonds with Rhodococcus rhodochrous

• Elaine O’Reilly,
• Suzanne J. Aitken,
• Gideon Grogan,
• Paul P. Kelly,
• Nicholas J. Turner and
• Sabine L. Flitsch

Beilstein J. Org. Chem. 2012, 8, 496–500, doi:10.3762/bjoc.8.56

• the selectivity of Beauveria bassiana ATCC 7159 [16][17]. Interestingly, the introduction of substituents on the aryl ring of some substrates can assist in directing hydroxylation away from the substituted position and can improve regioselectivity. For example, varying the aryl ring substituents on N

The interplay of configuration and conformation in helical perylenequinones: Insights from chirality induction in liquid crystals and calculations

• Elisa Frezza,
• Silvia Pieraccini,
• Stefania Mazzini,
• Alberta Ferrarini and
• Gian Piero Spada

Beilstein J. Org. Chem. 2012, 8, 155–163, doi:10.3762/bjoc.8.16

• the helical structure. X-ray crystallography established the R,R configuration at C14 and C17 of cercosporin (1) and the sign of the axial chirality as M [26][28]. Phleichrome (2) features opposite chirality, having P axial chirality and S,S configuration at C14 and C17 [27]. The ring substituents