Dioxazolones as electrophilic amide sources in copper-catalyzed and -mediated transformations

• Seungmin Lee,
• Minsuk Kim,
• Hyewon Han and
• Jongwoo Son

Beilstein J. Org. Chem. 2025, 21, 200–216, doi:10.3762/bjoc.21.12

• Synthesis of primary amides via the generation of copper–imidate radical intermediates In a subsequent study, the research group of Son developed a method for the reduction of dioxazolones to synthesize primary amides under mild reducing conditions in copper catalysis (Scheme 10) [103]. The reaction was

• conducted using a catalytic amount of copper acetate and a phenanthroline ligand, with a stoichiometric amount of silane serving as the reductant. Both aryl- and alkyl-substituted dioxazolones proved to be compatible under the standard reaction conditions, yielding the desired primary amides 28a–f. Notably

• , dioxazolones containing free -OH groups exhibited excellent functional group tolerance, leading to the formation of primary amides 28g and 28h. Moreover, biologically relevant scaffolds on dioxazolones were successfully transformed in this transformation (28i–k). As illustrated in Figure 9, a catalytic cycle

Clauson–Kaas pyrrole synthesis using diverse catalysts: a transition from conventional to greener approach

• Dileep Kumar Singh and
• Rajesh Kumar

Beilstein J. Org. Chem. 2023, 19, 928–955, doi:10.3762/bjoc.19.71

• (P2O5) as a catalyst for the conversion of various aliphatic amines, aromatic amines, sulfonamides and primary amides into N-substituted pyrroles (Scheme 5). These pyrroles were synthesized in 46–100% yields by the modified Clauson–Kaas reaction between amines 10 and 2,5-DMTHF (2) in the presence of

When metal-catalyzed C–H functionalization meets visible-light photocatalysis

• Lucas Guillemard and
• Joanna Wencel-Delord

Beilstein J. Org. Chem. 2020, 16, 1754–1804, doi:10.3762/bjoc.16.147

• aromatic coupling partner, including frequently used Weinreb amides or functionalized secondary and primary amides. Regarding the scope of olefin substrates, the reaction tolerated numerous functional groups including acrylates, vinyl silanes or sulfones which was interesting from the post

Installation of -SO₂F groups onto primary amides

• Jing Liu,
• Shi-Meng Wang,
• Njud S. Alharbi and
• Hua-Li Qin

Beilstein J. Org. Chem. 2019, 15, 1907–1912, doi:10.3762/bjoc.15.186

• Sciences, Faculty of Science, King Abdulaziz University, Jeddah, Saudi Arabia 10.3762/bjoc.15.186 Abstract A protocol of SO2F2-mediated installation of sulfonyl fluoride onto primary amides has been developed providing a new portal to sulfur(VI) fluoride exchange (SuFEx) click chemistry. The generated

• molecules contain pharmaceutically important amide and -SO2F moieties for application in the discovery of new therapeutics. Keywords: N-fluorosulfonyl amides; primary amides; sulfuryl fluoride (SO2F2); Introduction Sulfur(VI) fluoride exchange (SuFEx) is a new class of click chemistry developed by

• carboxylic amides (1r–u) were well-tolerated and afforded the target products in 56–90% yields. In addition, alkyl carboxylic amides were also smoothly transformed into the corresponding products (2v–z). However, primary amides bearing an amino group or a phenolic hydroxy group were not successfully

Synthesis of functionalised β-keto amides by aminoacylation/domino fragmentation of β-enamino amides

• Pavel Yanev and
• Plamen Angelov

Beilstein J. Org. Chem. 2018, 14, 2602–2606, doi:10.3762/bjoc.14.238

• enolates is one of the main synthetic approaches towards β-keto amides and has found numerous applications [1][2][3][4][5][6][7][8][9]. However, while the generation of tertiary amide enolates is straightforward, this is not the case with secondary and primary amides. The NH acidity of the latter compounds

Quinone-catalyzed oxidative deformylation: synthesis of imines from amino alcohols

• Xinyun Liu,
• Johnny H. Phan,
• Benjamin J. Haugeberg,
• Shrikant S. Londhe and
• Michael D. Clift

Beilstein J. Org. Chem. 2017, 13, 2895–2901, doi:10.3762/bjoc.13.282

• , entries 8−10). Unfortunately, only sulfinamide 6t provided the desired imine 7t (Table 3, entry 10, 22% yield). In all three cases, a significant amount of benzaldehyde was observed, indicating that electron deficient primary amides (such as 6r−t) are either incapable of promoting transimination, or the

Regiodivergent condensation of 5-alkoxycarbonyl-1H-pyrrol-2,3-diones with cyclic ketazinones en route to spirocyclic scaffolds

• Alexey Yu. Dubovtsev,
• Maksim V. Dmitriev,
• Аndrey N. Maslivets and
• Michael Rubin

Beilstein J. Org. Chem. 2017, 13, 2179–2185, doi:10.3762/bjoc.13.218

• attack of the amine moiety on the ester substituent (Scheme 1). Interestingly, it seems that the substitution at the nitrogen atom in structure 1 is very crucial in governing the desired reactivity. Indeed, our previous attempts to expand the substrate scope to include “vinylogous primary amides” 1a

Development of a method for the synthesis of 2,4,5-trisubstituted oxazoles composed of carboxylic acid, amino acid, and boronic acid

• Kohei Yamada,
• Naoto Kamimura and
• Munetaka Kunishima

Beilstein J. Org. Chem. 2017, 13, 1478–1485, doi:10.3762/bjoc.13.146

• materials, such as α-haloketones and primary amides [8], alkynes and nitriles [9], amines and α,β-unsaturated carbonyl compounds [10], etc. [11] have been reported. However, these reactions are often conducted under harsh reaction conditions and multistep syntheses of the starting materials are needed. ii

Recent advances in copper-catalyzed C–H bond amidation

• Jie-Ping Wan and
• Yanfeng Jing

Beilstein J. Org. Chem. 2015, 11, 2209–2222, doi:10.3762/bjoc.11.240

• catalysis of CuBr and NBS. By simply stirring at rt, 75 or 90 °C, a variety of primary amides and lactams incorporated aldehydes 57 to yield imides 58 with moderate to excellent yield. In addition, the method also displayed sound application in the synthesis of cyclic imides such as N-methylphthalimide (60

Integration of enabling methods for the automated flow preparation of piperazine-2-carboxamide

• Richard J. Ingham,
• Claudio Battilocchio,
• Joel M. Hawkins and
• Steven V. Ley

Beilstein J. Org. Chem. 2014, 10, 641–652, doi:10.3762/bjoc.10.56

• molecule to the substrate with no byproducts: the addition of water for the nitrile hydration, and the addition of hydrogen to the heteroarene for the reduction. Thus, this sequence is ideal for a fully continuous multi-step process. Results and Discussion Nitrile hydration Primary amides can be prepared

The chemistry of amine radical cations produced by visible light photoredox catalysis

• Jie Hu,
• Jiang Wang,
• Theresa H. Nguyen and
• Nan Zheng

Beilstein J. Org. Chem. 2013, 9, 1977–2001, doi:10.3762/bjoc.9.234

• ketones failed to provide the desired products. Amides 68 are generally much more difficult to be oxidized than amines. Their reduction potentials range from 1.2–1.5 V (vs SCE) for tertiary amides to 2.0 V (vs SCE) for primary amides [84] which makes them less susceptible to oxidation by the photoexcited

EcoScale, a semi- quantitative tool to select an organic preparation based on economical and ecological parameters

• Koen Van Aken,
• Lucjan Strekowski and
• Luc Patiny

Beilstein J. Org. Chem. 2006, 2, No. 3, doi:10.1186/1860-5397-2-3

• claim that this procedure for preparing primary amides starting from aryl halides is better than another procedure which uses hexamethyldisilazane (HMDS). [26] Therefore, the EcoScale for the latter procedure was also calculated to compare the two preparations. The sum of all penalty points is 68 (Table