Benzoimidazolium-derived dimeric and hydride n-dopants for organic electron-transport materials: impact of substitution on structures, electrochemistry, and reactivity

• Swagat K. Mohapatra,
• Khaled Al Kurdi,
• Samik Jhulki,
• Georgii Bogdanov,
• John Bacsa,
• Maxwell Conte,
• Tatiana V. Timofeeva,
• Seth R. Marder and
• Stephen Barlow

Beilstein J. Org. Chem. 2023, 19, 1651–1663, doi:10.3762/bjoc.19.121

• condensation between phenylene-1,2-diamines and carboxylic acids YCO2H [28], oxidative condensation between YCHO and phenylene-1,2-diamines [29], or reductive condensation between YCHO and 2-nitroanilines [24]. In this work we condensed the appropriate YCHO aldehyde (II) and 1,2-diaminobenzene (I) derivatives

One-pot and metal-free synthesis of 3-arylated-4-nitrophenols via polyfunctionalized cyclohexanones from β-nitrostyrenes

• Haruyasu Asahara,
• Minami Hiraishi and
• Nagatoshi Nishiwaki

Beilstein J. Org. Chem. 2020, 16, 1830–1836, doi:10.3762/bjoc.16.150

• preparing the precursor [10]. The condensation of benzyl methyl ketone with a nitrovinamidinium salt also affords 3-arylated-4-nitrophenols; however, 3-arylated-N,N-dimethyl-4-nitroanilines are competitively formed in this reaction [11]. Hence, there is an urgent demand for the development of a facile

Recent developments in photoredox-catalyzed remote ortho and para C–H bond functionalizations

• Rafia Siddiqui and
• Rashid Ali

Beilstein J. Org. Chem. 2020, 16, 248–280, doi:10.3762/bjoc.16.26

• assembled using this strategy, as displayed in Scheme 15, and a plausible mechanism for the reaction is shown in Figure 16. C–H nitration of protected anilines Nitroanilines are an important class of compounds and found in many drugs and dyes [144]. Therefore, recently, König and co-worker reported the

Hyper-reticulated calixarene polymers: a new example of entirely synthetic nanosponge materials

• Alberto Spinella,
• Marco Russo,
• Antonella Di Vincenzo,
• Delia Chillura Martino and
• Paolo Lo Meo

Beilstein J. Org. Chem. 2018, 14, 1498–1507, doi:10.3762/bjoc.14.127

• which several techniques have been exploited, spanning from oxidation to photodegradation. Tests were performed only with materials CaNS2 and CaNS4, which appeared on average the best absorbents towards p-nitroanilines. The results of the sequestration tests on dyes 6–10 are summarized in Table 2

The first Pd-catalyzed Buchwald–Hartwig aminations at C-2 or C-4 in the estrone series

• Ildikó Bacsa,
• Dávid Szemerédi,
• János Wölfling,
• Gyula Schneider,
• Lilla Fekete and
• Erzsébet Mernyák

Beilstein J. Org. Chem. 2018, 14, 998–1003, doi:10.3762/bjoc.14.85

• different substituents at o, m or p positions (Scheme 1). As indicated in Scheme 1, all couplings proceeded with high yields. The best yields were achieved with nitroanilines, irrespective of the position of the nitro group. Reaction of methylanilines led to slightly lower yields, indicating that the

From dipivaloylketene to tetraoxaadamantanes

• Gert Kollenz and
• Curt Wentrup

Beilstein J. Org. Chem. 2018, 14, 1–10, doi:10.3762/bjoc.14.1

• electron-withdrawing groups (nitroanilines) do not form stable bisdioxines such as 8. Instead, a cleavage of the dioxinone ring in 3 with formation of dipivaloylacetamides takes place. Surprisingly, the more basic aliphatic amines also cause cleavage to dipivaloylacetamides. On the other hand, neutral

Binding abilities of polyaminocyclodextrins: polarimetric investigations and biological assays

• Marco Russo,
• Daniele La Corte,
• Annalisa Pisciotta,
• Serena Riela,
• Rosa Alduina and
• Paolo Lo Meo

Beilstein J. Org. Chem. 2017, 13, 2751–2763, doi:10.3762/bjoc.13.271

• our materials to exploit both the cavity and the polycationic branches, thus functioning as bimodal ligands. Keywords: aminocyclodextrins; binding properties; nitroanilines; pDNA; polarimetry; supramolecular chemistry; Introduction Polyamine macromolecules have attracted a widespread interest for

• protonation step at each polyamine branch occurs. This suggests the presence of strong intrachain interactions before protonation. Binding abilities of AmCDs towards p-nitroaniline derivatives 1–4 p-Nitroanilines constitute a good class of probe molecules for testing the microscopic behaviour of cyclodextrins

• values for p-nitroanilines are affected by an induced circular dichroism effect due to the interaction between the dipole moments of the polarized chromophore guest moiety and of the cyclodextrin cavity. Therefore, these parameters provide an estimation of the time-averaged tilt angle between the

Binding abilities of a chiral calix[4]resorcinarene: a polarimetric investigation on a complex case of study

• Marco Russo and
• Paolo Lo Meo

Beilstein J. Org. Chem. 2017, 13, 2698–2709, doi:10.3762/bjoc.13.268

• : calix[4]resorcinarene; host–guest complexes; p-nitroanilines; polarimetry; supramolecular chemistry; Introduction During the last decades calix[n]arenes and calix[n]resorcinarenes (CAs) have emerged as versatile supramolecular host systems for various applications [1][2][3][4][5], spanning from sensors

Continuous flow nitration in miniaturized devices

• Amol A. Kulkarni

Beilstein J. Org. Chem. 2014, 10, 405–424, doi:10.3762/bjoc.10.38

• . Among the other basic chemicals that are used in significantly large quantities are a large number of organic molecules, e.g., nitrobenzenes, nitrophenols, nitrotoluenes, nitroxylenes, nitronaphthalenes, nitrohaloaromatics, nitroanilines, nitrotoluidines, imidazole derivatives, nitroketones, pyridine

Asymmetric synthesis of host-directed inhibitors of myxoviruses

• Terry W. Moore,
• Kasinath Sana,
• Dan Yan,
• Pahk Thepchatri,
• John M. Ndungu,
• Manohar T. Saindane,
• Mark A. Lockwood,
• Michael G. Natchus,
• Dennis C. Liotta,
• Richard K. Plemper,
• James P. Snyder and
• Aiming Sun

Beilstein J. Org. Chem. 2013, 9, 197–203, doi:10.3762/bjoc.9.23

• compounds. Synthesis. The compounds were prepared by modifications of our previously reported routes. Briefly, nitroanilines 7 were obtained by one of two routes: ortho-nitrobenzaldehyde (2) was treated with N-methylpiperazine (3) in the presence of sodium triacetoxyborohydride to give nitrobenzene 4, which

• ) to deliver o-nitroanilines 9. The hydroxy groups of 9 were activated as the p-nitrobenzenesulfonates 10 and displaced with morpholine to give o-nitroanilines 7b and 7c (Scheme 2). Hydrogenation was used to reduce o-nitroanilines 7 followed by cyclization using thiocarbonyldiimidazole to yield

• )- (left, magenta) and (R)- (right, cyan) enantiomers of 1. L-Tartaric acid salt (18f-tartrate) and benzenesulfonic acid salt (18f-benzenesulfonate) of 18f. Synthesis of anilino nitrobenzene 7a. Preparation of morpholinyl-o-nitroanilines. Asymmetric synthesis of (R)- and (S)-isomers by using two different

Imidazole as a parent π-conjugated backbone in charge-transfer chromophores

• Jiří Kulhánek and
• Filip Bureš

Beilstein J. Org. Chem. 2012, 8, 25–49, doi:10.3762/bjoc.8.4

• condensation of appropriately substituted arylenediamines or o-nitroanilines with an aldehyde or carboxylic acid, as well as Debus–Radziszewski synthesis as shown in Scheme 1 [23][24][25][26]. Since the discovery and the first synthesis of 4,5-dicyanoimidazole was reported by Woodward [27], this imidazole

A novel high-yield synthesis of aminoacyl p-nitroanilines and aminoacyl 7-amino-4-methylcoumarins: Important synthons for the synthesis of chromogenic/fluorogenic protease substrates

• Xinghua Wu,
• Yu Chen,
• Herve Aloysius and
• Longqin Hu

Beilstein J. Org. Chem. 2011, 7, 1030–1035, doi:10.3762/bjoc.7.117