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

• Giovanni S. Baviera Paulo M. Donate Departamento de Química, Faculdade de Filosofia, Ciências e Letras de Ribeirão Preto, Universidade de São Paulo, 14040-091, Ribeirão Preto, SP, Brazil 10.3762/bjoc.17.131 Abstract Anthracene and anthracene derivatives have been extensively studied over the

• materials. Their synthesis remains challenging, but some important preparative methods have been reported, especially in the last decade. This review presents an update of the recent strategies that have been employed to prepare anthracene derivatives. It encompasses papers published over the last twelve

• three linearly fused benzene rings. Because of their extended aromatic and conjugated π-system, anthracene derivatives possess interesting photochemical and photophysical properties [1][2][3], as well as gelling ability [4]. These important properties make them relevant for the development and

Articulated rods – a novel class of molecular rods based on oligospiroketals (OSK)

• Pablo Wessig,
• Roswitha Merkel and
• Peter Müller

Beilstein J. Org. Chem. 2015, 11, 74–84, doi:10.3762/bjoc.11.11

• [4 + 4] photocycloaddition of anthracene derivatives. At first we pursued a sequential approach by introducing the pyrene-1-ylacetyl and the cinnamoyl moieties in a two-step sequence in 4-hydroxypiperidine with subsequent oxidation to give piperidin-4-ones 27a,b. An appropriate anthracene derivative

Integrating reaction and analysis: investigation of higher-order reactions by cryogenic trapping

• Skrollan Stockinger and
• Oliver Trapp

Beilstein J. Org. Chem. 2013, 9, 1837–1842, doi:10.3762/bjoc.9.214

• presented. The reaction and the analytical separation are combined in a single experiment to investigate the Diels–Alder reaction of benzenediazonium-2-carboxylate as a benzyne precursor with various anthracene derivatives, i.e. anthracene, 9-bromoanthracene, 9-anthracenecarboxaldehyde and 9

• our novel ocRGC setup, we chose the cycloaddition of benzyne with anthracene derivatives in a typical Diels–Alder-reaction (Scheme 1) as a model reaction. This reaction seemed suitable because of the volatility of all reactants and products and the required reaction temperature, which is in an

• -triptycenemethanol for the on-column measurement can be considered as an impressing result. Unfortunately, all other anthracene derivatives did not exceed a yield of 2% with the ocRGC method. For the test-tube experiments the yield of 9-anthracenemethanol is also higher than those of the other derivatives, but the

Spectroscopic characterization of photoaccumulated radical anions: a litmus test to evaluate the efficiency of photoinduced electron transfer (PET) processes

• Maurizio Fagnoni,
• Stefano Protti,
• Davide Ravelli and
• Angelo Albini

Beilstein J. Org. Chem. 2013, 9, 800–808, doi:10.3762/bjoc.9.91

• solution) in the presence of tertiary amines allowed the accumulation of the corresponding radical anions, up to quantitative yield for polysubstituted benzenes and partially with naphthalene and anthracene derivatives. The condition for such an accumulation was that the donor radical cation underwent

Computational evidence for intramolecular hydrogen bonding and nonbonding X···O interactions in 2'-haloflavonols

• Tânia A. O. Fonseca,
• Matheus P. Freitas,
• Rodrigo A. Cormanich,
• Teodorico C. Ramalho,
• Cláudio F. Tormena and
• Roberto Rittner

Beilstein J. Org. Chem. 2012, 8, 112–117, doi:10.3762/bjoc.8.12

• more unusual stabilizing interactions are the nonbonding F···O interactions, which were experimentally and theoretically characterized in anthracene derivatives, and were pointed out to be the responsible interactions behind the unusual “through-space” fluorine–fluorine spin–spin coupling in the F···O

Functionalization of anthracene: A selective route to brominated 1,4-anthraquinones

• Kiymet Berkil Akar,
• Osman Cakmak,
• Orhan Büyükgüngör and
• Ertan Sahin

Beilstein J. Org. Chem. 2011, 7, 1036–1045, doi:10.3762/bjoc.7.118

• derivatives that are difficult to prepare by other routes. The studies also reveal the broad range of reactivity and selectivity of the stereoisomeric anthracene derivatives. Keywords: anthracene derivatives; anthracene-1,4-dione; aromatization; bromination; bromoanthracene; methoxyanthracene; silver-induced

• this work, we report on new methoxy and hydroxy derivatives of anthracene, whose further transformation generates synthetically important novel anthracene derivatives. We also report an effective synthetic route to 1,4-dione 28 starting from 9,10-dibromoanthracene (1) in four steps. The compounds

• with no aliphatic carbon but two carbonyl signals at δ 177.0 and δ 174.3, respectively. Conclusion This report and our previous studies [1][2] demonstrate that the reactivity and selectivity of the stereoisomeric anthracene derivatives strongly depend on both, the reaction conditions and their

9,10-Dioxa-1,2-diaza-anthracene derivatives from tetrafluoropyridazine

• Graham Pattison,
• Graham Sandford,
• Dmitrii S. Yufit,
• Judith A. K. Howard,
• John A. Christopher and
• David D. Miller

Beilstein J. Org. Chem. 2010, 6, No. 45, doi:10.3762/bjoc.6.45

• describe the synthesis of dioxa-1,2-diaza-anthracene derivatives by the sequential reaction of commercially available tetrafluoropyridazine with catechol, and a short series of nucleophiles. Results and Discussion Initially, we carried out reactions of tetrafluoropyridazine (3) with one and two equivalents

• -diaza-anthracene derivatives. Reactions of tetrafluoropyridazine 3 with sodium phenoxide. Synthesis of dioxa-1,2-diaza-anthracene scaffold 5. Mechanism of formation of 5. Reactions of dioxa-1,2-diaza-anthracene scaffold 5 with nucleophiles. Supporting Information Supporting Information with 1H NMR and

Molecular recognition of organic ammonium ions in solution using synthetic receptors

• Andreas Späth and
• Burkhard König

Beilstein J. Org. Chem. 2010, 6, No. 32, doi:10.3762/bjoc.6.32

• potential use of these peptide nanostructures is as pro-drugs that may be activated by a specific proteolytic enzyme to target selectively and destroy undesirable cells [190]. Kim et al. reported two bis(azacrown)anthracene derivatives 48a and 48b (Figure 30) for the recognition and detection of

Reversible intramolecular photocycloaddition of a bis(9-anthrylbutadienyl)paracyclophane – an inverse photochromic system. (Photoactive cyclophanes 5)

• Henning Hopf,
• Christian Beck,
• Jean-Pierre Desvergne,
• Henri Bouas-Laurent,
• Peter G. Jones and
• Ludger Ernst

Beilstein J. Org. Chem. 2009, 5, No. 20, doi:10.3762/bjoc.5.20

• vinylogs studied so far [18][19], including compound 1 (λmax = 370 nm). The presence of the twisted butadienyl system introduces several torsional vibrations about the pseudo single bonds and attenuates the fine structure usually observed for anthracene derivatives (see Figure 6). The difference between

• protons H41 and H44 then display the peak at δ = 4.73 ppm, reflecting a very small coupling with their neighbours (H–C–C–H dihedral angles close to 90°) [23][24]. The majority of anthracene derivatives are known to undergo a [4+4]cycloaddition from the S1 state [11][12], but some [4+2]-cycloadditions were

Highly brominated anthracenes as precursors for the convenient synthesis of 2,9,10-trisubstituted anthracene derivatives

• Osman Cakmak,
• Leyla Aydogan,
• Kiymet Berkil,
• Ilhami Gulcin and
• Orhan Buyukgungor

Beilstein J. Org. Chem. 2008, 4, No. 50, doi:10.3762/bjoc.4.50

• tribromide 12 was transformed to trimethoxy compound 13 and trinitrile 14 by copper-assisted nucleophilic substitution reactions. Keywords: anthracene derivative; bromination; bromoanthracene; cyanoanthracene; methoxyanthracene; Introduction Anthracene derivatives have been extensively investigated in many

• biological systems, anthracene skeletal compounds are also useful for probing DNA cleavage [17]. Bromoanthracenes have become increasingly important in the synthesis of anthracene derivatives [18]. For example, new anthracene derivatives used as light emitting material in a non-doped organic light-emitting

• diode (OLED) were synthesized from the corresponding bromo derivatives by substitution [19][20][21][22][23]. Recently we succeeded in the bromination of anthracene to give hexabromides 3 and 4 which were used in the selective and specific preparation of anthracene oxides and anthracene derivatives