Copper-promoted C5-selective bromination of 8-aminoquinoline amides with alkyl bromides

• Changdong Shao,
• Chen Ma,
• Li Li,
• Jingyi Liu,
• Yanan Shen,
• Chen Chen,
• Qionglin Yang,
• Tianyi Xu,
• Zhengsong Hu,
• Yuhe Kan and
• Tingting Zhang

Beilstein J. Org. Chem. 2024, 20, 155–161, doi:10.3762/bjoc.20.14

• selective C5-bromination of 8-aminoquinoline amides using carbon tetrabromide and dibromomethane under photo- and electrocatalysis conditions [27][28]. In 2017, Xia and co-workers reported a novel, mild, metal-free, and regioselective bromination of amides, wherein the organic dye eosin Y acted as the

Brønsted acid-mediated cyclization–dehydrosulfonylation/reduction sequences: An easy access to pyrazinoisoquinolines and pyridopyrazines

• Ramana Sreenivasa Rao and
• Chinnasamy Ramaraj Ramanathan

Beilstein J. Org. Chem. 2017, 13, 428–440, doi:10.3762/bjoc.13.46

• phenyl group was proposed to introduce at the 3-position in substituted pyrazinone via regioselective bromination followed by Suzuki coupling with phenylboronic acid. Accordingly, the bromination of 10a was successfully carried out to furnish regioisomers 12a and 12b in 82% yield upon treatment with

[2.2]Paracyclophane derivatives containing tetrathiafulvalene moieties

• Laura G. Sarbu,
• Lucian G. Bahrin,
• Peter G. Jones,
• Lucian M. Birsa and
• Henning Hopf

Beilstein J. Org. Chem. 2015, 11, 1917–1921, doi:10.3762/bjoc.11.207

• -yl)-1,3-dithiol-2-thione in the presence of trimethylphosphite. The 1,3-dithiol-2-thione derivative was in turn synthesized by the regioselective bromination of 4-acetyl[2.2]paracyclophane, then through the corresponding dithiocarbamates and 1,3-dithiolium salts. Keywords: dithiocarbamates; 1,3

• -dithiolium salts; [2.2]paracyclophane; regioselective bromination; stereoisomers; tetrathiafulvalenes; Introduction Tetrathiafulvalene (TTF) and its derivatives have been extensively studied with respect to their applications as organic metals and superconductors [1][2]. These properties are a consequence

• 1,3-dithiol-2-ylium cation. This was in turn synthesized through a three-step procedure, starting with the regioselective bromination of 4-acetyl[2.2]paracyclophane. Molecular structure of compound 4a. Ellipsoids represent 30% probability levels. Selected molecular dimensions (Å, °): N(1)–C(19) 1.341

The synthesis of active pharmaceutical ingredients (APIs) using continuous flow chemistry

• Marcus Baumann and
• Ian R. Baxendale

Beilstein J. Org. Chem. 2015, 11, 1194–1219, doi:10.3762/bjoc.11.134

• also been employed in the flow synthesis of a carprofen analogue [69] as well as in the regioselective bromination towards a rosuvastatin precursor [70] showcasing how continuous flow photochemistry is receiving a significant level of interest. This is not least because of the perceived green reagent

An overview of the synthetic routes to the best selling drugs containing 6-membered heterocycles

• Marcus Baumann and
• Ian R. Baxendale

Beilstein J. Org. Chem. 2013, 9, 2265–2319, doi:10.3762/bjoc.9.265

• dihydropyridine. This regioselective bromination reaction was studied in some detail by the Warner–Lambert Company and is reported to give superior outcomes when compared to the direct Hantzsch synthesis of non-symmetrical dihydropyridines with respect to product yield (70–90% vs 10–30%) and ease of purification

Dioxane dibromide mediated bromination of substituted coumarins under solvent-free conditions

• Subrata Kumar Chaudhuri,
• Sanchita Roy and
• Sanjay Bhar

Beilstein J. Org. Chem. 2012, 8, 323–329, doi:10.3762/bjoc.8.35

• /bjoc.8.35 Abstract An efficient solvent-free protocol for regioselective bromination of substituted coumarins has been developed by using dioxane dibromide as the solid brominating agent. The efficacy of the solvent-free protocol has been established. The effects of the electronic nature and location

• diseases [4]. Halocoumarins also exhibit insecticidal and fungicidal properties [5]. A few methods have been documented for regioselective bromination of coumarins, which include CuBr2/Al2O3 in bromobenzene under reflux [5], Br2 in glacial AcOH [6], Br2/Al2O3 under microwave irradiation [7], NBS in CHCl3

• of new methods for regioselective bromination of differently substituted coumarins under mild conditions with easily accessible reagents. Dioxane dibromide (DD) has been successfully used for selective α-bromination of substituted acetophenones by using dioxane as a solvent at room temperature [12