Mechanochemical halogenation of unsymmetrically substituted azobenzenes

• Dajana Barišić,
• Mario Pajić,
• Ivan Halasz,
• Darko Babić and
• Manda Ćurić

Beilstein J. Org. Chem. 2022, 18, 680–687, doi:10.3762/bjoc.18.69

• for the selective imidation of azobenzenes containing a dimethylamino group as substituent in the para position to the azo group. Results and Discussion Inspired by our findings on the mechanochemical halogenation of L1 [51] and the report of Ma and Tian on the bromination of symmetric and unsymmetric

• yield of 30% after one hour of milling (Table 1, entry 10 and Figures S77–S81 in Supporting Information File 1). Interestingly, in the reactions of L4 and L5 with NIS, instead of the halogenation of the aromatic C–H bond, imidation of the aliphatic C–H bond was observed. Imides are among the most

• Supporting Information File 1). The molecular structure of L4-III showed that imidation occurred at the methyl group of the NMe2 substituent. Analogous succinimide species were also observed in the reaction of N,N-dimethyl-p-toluidine with NIS in ethyl acetate [55] or N,N-dimethylamides and N,N

Direct C–H amination reactions of arenes with N-hydroxyphthalimides catalyzed by cuprous bromide

• Dongming Zhang,
• Bin Lv,
• Pan Gao,
• Xiaodong Jia and
• Yu Yuan

Beilstein J. Org. Chem. 2022, 18, 647–652, doi:10.3762/bjoc.18.65

• the corresponding products in good yields. In addition, employing furan as the substrate, imidation occurred only at the ortho position to provide 3q with a moderate 33% yield. Finally, various substituted N-hydroxyphthalimides were studied (Scheme 3), and the desired N-phthalimide products 3r–u were

• gel (ethyl acetate/petroleum ether 1:10) to afford the desired products 3a–u. Amination of arenes with phthalimides. Substrate scope of the copper-catalyzed C–H imidation of arenes. Reaction conditions: 1 (2.0 mL as substrate and solvent), 2a (0.10 mmol), CuBr (0.04 mmol) and P(OEt)3 (0.6 mmol) were

• stirred for 12 h at 100 °C under air. a = ortho-, b = meta-, c = para-. Substrate scope of the copper-catalyzed C–H imidation of N-hydroxyphthalimide. Reaction conditions: 1a (2.0 mL as substrate and solvent), 2 (0.10 mmol), CuBr (0.04 mmol) and P(OEt)3 (0.6 mmol) were stirred for 12 h at 100 °C under air

Nocarimidazoles C and D, antimicrobial alkanoylimidazoles from a coral-derived actinomycete Kocuria sp.: application of ¹J_C,H coupling constants for the unequivocal determination of substituted imidazoles and stereochemical diversity of anteisoalkyl chains in microbial metabolites

• Md. Rokon Ul Karim,
• Enjuro Harunari,
• Amit Raj Sharma,
• Naoya Oku,
• Kazuaki Akasaka,
• Daisuke Urabe,
• Mada Triandala Sibero and
• Yasuhiro Igarashi

Beilstein J. Org. Chem. 2020, 16, 2719–2727, doi:10.3762/bjoc.16.222

• commercially available imidazole derivative, 4-isocyano-1H-imidazol-5-amine, with MeMgBr. On the other hand, 9 was synthesized in three steps from pyrimidin-2-amine. Imidation of the starting material with 1,1-dimethoxy-N,N-dimethylmethylamine gave an N,N- dimethylformimidamide derivative, which was cyclized

β-Hydroxy sulfides and their syntheses

• Mokgethwa B. Marakalala,
• Edwin M. Mmutlane and
• Henok H. Kinfe

Beilstein J. Org. Chem. 2018, 14, 1668–1692, doi:10.3762/bjoc.14.143

• the N-Boc protected β-hydroxy sulfide 130 as a key intermediate. Deprotection of the Boc followed by the imidation of the free amine with protected dipeptides that mimic Leu-Val produced the inhibitors of human renin 131 as depicted in Scheme 44. Yoshioka and co-workers reported two synthetic routes

Polysubstituted ferrocenes as tunable redox mediators

• Sven D. Waniek,
• Jan Klett,
• Christoph Förster and
• Katja Heinze

Beilstein J. Org. Chem. 2018, 14, 1004–1015, doi:10.3762/bjoc.14.86

• reactions [29], borylations of arenediazonium salts [30] and in C–H imidation reactions of (hetero)arenes [31] (Scheme 1b,c). Ferrocene has been used as redox mediator for the electrochemical modification of carbon surfaces via electrochemical oxidation of carboxylates [32][33], as mediator for

One-pot syntheses of blue-luminescent 4-aryl-1H-benzo[f]isoindole-1,3(2H)-diones by T3P^® activation of 3-arylpropiolic acids

• Melanie Denißen,
• Alexander Kraus,
• Guido J. Reiss and
• Thomas J. J. Müller

Beilstein J. Org. Chem. 2017, 13, 2340–2351, doi:10.3762/bjoc.13.231

• in the vibrationally relaxed excited singlet state. Keywords: absorption; cycloaddition; diversity-oriented synthesis; fluorescence; heterocycles; imidation; Introduction Luminophores as functional π-electron systems [1] are crucial in modern illumination technologies, such as organic light

• can be increased to 47% upon raising the reaction temperature to 115 °C (Table 3, entry 3), however, higher temperatures, such as 160 °C, cause a significant drop in yield. Finally, at 115 °C with two equivalents of aniline the highest yield can be achieved (Table 3, entry 6). These imidation

• conditions are well-suited for concatenating the arylpropiolic anhydride formation, intramolecular cycloaddition and imidation in a one-pot fashion in the sense of a consecutive pseudo three-component synthesis of 4-aryl-1H-benzo[f]isoindole-1,3(2H)-diones 4, which was first probed with an electroneutral (1a

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

• sulfonamidation and imidation) reactions under the categories of C(sp3)–H bond amidation, C(sp2)–H bond amidation, C(sp)–H bond amidation and cascade reactions initiated by C–H amidation. Review C(sp3)–H bond amidation Intermolecular amidation The formation of N-alkylamides could be traditionally accessed via

• , Hartwig and co-workers [50] successfully realized the amidation, sulfonamidation and imidation reactions of purely non-activated cyclic and linear alkanes via the catalysis of copper(I) iodide by employing 4,7-dimethoxyphenanthroline ((OMe)2Phen) as the ligand and t-BuOOt-Bu as an oxidant. Heating the

• for lactam synthesis. Copper-catalyzed amidation/sulfonamidation of aryl C–H bonds. C–H amidation of pyridinylbenzenes and indoles. Mechanism of the Cu-catalyzed C2-amidation of indoles. Copper-catalyzed, 2-phenyl oxazole-assisted C–H amidation of benzamides. DG-assisted amidation/imidation of indole

Multistep organic synthesis of modular photosystems

• Naomi Sakai and
• Stefan Matile

Beilstein J. Org. Chem. 2012, 8, 897–904, doi:10.3762/bjoc.8.102

• and alkylation with ethyl bromoacetate (10) gave ethyl ester 11, and final ester hydrolysis lead to the desired acid 7. The peripheral NDIs 12, designed to template for stack exchange on initiator 2, were prepared from naphthalenedianhydride (NDA) 13. Microwave-assisted imidation [15] with the two

• NDI 18 of initiator 2, designed to initiate and template for SOSIP, was accessible from NDA 13 as well. The synthesis of NDI 19 by microwave-assisted imidation with Boc-protected lysine 20 has been reported before in the literature [15]. Reaction with Cbz-hydrazine gave the Cbz-protected NDI hydrazide