New efficient synthesis of polysubstituted 3,4-dihydroquinazolines and 4H-3,1-benzothiazines through a Passerini/Staudinger/aza-Wittig/addition/nucleophilic substitution sequence

• Long Zhao,
• Mao-Lin Yang,
• Min Liu and
• Ming-Wu Ding

Beilstein J. Org. Chem. 2022, 18, 286–292, doi:10.3762/bjoc.18.32

• ]. Some 4H-3,1-benzothiazines were prepared by intramolecular thia-Michael addition with broad reaction scopes [19]. The rearrangement of 2-isothiocyano triarylmethanes in the presence of AlCl3 were also used for the synthesis 2,4-diaryl-4H-3,1-benzothiazines through aromatic ring transfer [20]. A facile

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

• convenient synthesis of triarylmethanes and 9,10-diarylanthracenes from reactions of arenes and aromatic aldehydes by using acetyl bromide in the presence of silica gel-supported zinc bromide [43]. The methodology developed by these authors involved using excess of one of the reagents. When the authors

• , the authors added previously prepared triarylmethanes 52 to the reaction mixture under air atmosphere, and then under oxygen atmosphere. Therefore, an efficient Bi(OTf)3/O2 system promoted the oxidation/aromatization step, providing the 9,10-disubstituted 2,3,6,7-tetraalkoxyanthracenes 53 in good

• . Alkylation of arenes with aromatic aldehydes in the presence of acetyl bromide and ZnBr2/SiO2. BF3·H2O-catalyzed hydroxyalkylation of arenes with aromatic dialdehyde 44. Bi(OTf)3-promoted Friedel–Crafts alkylation of triarylmethanes and aromatic acylals and of arenes and aromatic aldehydes. Reduction of

Catalyst-free assembly of giant tris(heteroaryl)methanes: synthesis of novel pharmacophoric triads and model sterically crowded tris(heteroaryl/aryl)methyl cation salts

• Rodrigo Abonia,
• Luisa F. Gutiérrez,
• Braulio Insuasty,
• Jairo Quiroga,
• Kenneth K. Laali,
• Chunqing Zhao,
• Gabriela L. Borosky,
• Samantha M. Horwitz and
• Scott D. Bunge

Beilstein J. Org. Chem. 2019, 15, 642–654, doi:10.3762/bjoc.15.60

• ][14][15][16][17][18][19][20][21][22]. Although, “Yonemitsu-type” three-component reactions have been employed for the synthesis of indole-based triarylmethanes [23][24][25][26] (Scheme 2), there still exists a need for the development of new approaches for easy access to libraries of triarylmethanes

Mannich base-connected syntheses mediated by ortho-quinone methides

• Petra Barta,
• Ferenc Fülöp and
• István Szatmári

Beilstein J. Org. Chem. 2018, 14, 560–575, doi:10.3762/bjoc.14.43

• successfully developed a rhodium-catalyzed asymmetric arylation process leading to triarylmethanes 25. With the application of mild reaction conditions (40 °C, 15 h), a high enantioselectivity (≥90% ee) was reached with good to excellent yields. (Scheme 2). Starting from 2-naphthol, 2,2-disubstituted 3

• intermediate 3. Asymmetric syntheses of triarylmethanes starting from diarylmethylamines. Proposed mechanism for the formation of 2,2-dialkyl-3-dialkylamino-2,3-dihydro-1H-naphtho[2,1-b]pyrans 32. Cycloadditions of isoflavonoid-derived o-QMs and various dienophiles. [4 + 2] Cycloaddition reactions between

Detection of therapeutic radiation in three-dimensions

• John A. Adamovics

Beilstein J. Org. Chem. 2017, 13, 1325–1331, doi:10.3762/bjoc.13.129

• triarylmethane (DTM) [17]. Triarylmethanes (TAMs) have wide ranging commercial, technological and medical applications [17]. In mechanistic chemistry, a triarylmethane demonstrated the first observable organic radical species [18]. TAMs were first synthesized using the Baeyer condensation in 1877 where one

• -anthracenecarboxaldehyde, and 1-pyrenecarboxaldehyde, yielded no detectable DTM products. N,N,N-trialkyl-substituted triarylmethanes (e.g., leuco crystal violet) were also synthesized using the above synthetic procedures (e.g., 4-dimethylaminobenzaldehyde as starting aryl aldehyde) but these were too easily oxidized

The reductive decyanation reaction: an overview and recent developments

• Jean-Marc R. Mattalia

Beilstein J. Org. Chem. 2017, 13, 267–284, doi:10.3762/bjoc.13.30

• organometallic reagents or other nucleophiles [139]. Nambo et al described the preparation of triarylacetonitriles using sequential Pd-catalyzed arylations. Triarylacetonitriles obtained can be transformed into various species including triarylmethanes by treatment with MeMgCl (Scheme 30) [140]. In this case a

Copper-mediated arylation with arylboronic acids: Facile and modular synthesis of triarylmethanes

• H. Surya Prakash Rao and
• A. Veera Bhadra Rao

Beilstein J. Org. Chem. 2016, 12, 496–504, doi:10.3762/bjoc.12.49

• H. Surya Prakash Rao A. Veera Bhadra Rao Department of Chemistry, Pondicherry University, Pondicherry 605 014, India Telephone: +914132654411; Fax: +914132656230 10.3762/bjoc.12.49 Abstract A facile and modular synthesis of triarylmethanes was achieved in good yield via a two-step sequence in

• which the final step is the copper(II)-catalyzed arylation of diarylmethanols with arylboronic acids. By using this protocol a variety of symmetrical and unsymmetrical triarylmethanes were synthesized. As an application of the newly developed methodology, we demonstrate a high-yielding synthesis of the

• triarylmethane intermediate towards an anti-breast-cancer drug candidate. Keywords: copper; modular synthesis; triarylmethanes; Introduction The triarylmethanes form an exclusive group of organic molecules wherein three aryl groups are attached to the central sp3-hybridized carbon atom bearing a hydrogen atom

Hydrophobic analogues of rhodamine B and rhodamine 101: potent fluorescent probes of mitochondria in living C. elegans

• Laurie F. Mottram,
• Safiyyah Forbes,
• Brian D. Ackley and
• Blake R. Peterson

Beilstein J. Org. Chem. 2012, 8, 2156–2165, doi:10.3762/bjoc.8.243

• the corresponding dialkyaminophenol with o-tolualdehyde (12) [39]. Oxidative cyclization of triarylmethanes with the quinone oxidant chloranil provided 9 and 10 in modest yield. 8-Hydroxyjulolidine (14) for synthesis of HR101 10 was either purchased commercially or prepared as previously described [40

SbCl₃-catalyzed one-pot synthesis of 4,4′-diaminotriarylmethanes under solvent-free conditions: Synthesis, characterization, and DFT studies

• Ghasem Rezanejade Bardajee

Beilstein J. Org. Chem. 2011, 7, 135–144, doi:10.3762/bjoc.7.19

• variety of aryl and heteroaryl aldehydes under solvent-free conditions to give substituted triarylmethanes. Using SbCl3 as catalyst, even electron-rich benzaldehydes such as 3,4,5-trimethoxybenzaldehyde gave the corresponding products in good yields. Operational simplicity, high yields, and the ability to

• prepare a wide range of products are the advantages of this protocol. Molecular geometry parameters and vibrational wavenumbers of the triarylmethanes have been obtained from theoretical calculations for the first time. The theoretical results show good agreement between theoretical and experimental data