Indium(iii)-catalyzed efficient synthesis of 3-arylhydrazonoindolin-2-ones and their fluorescent metal sensing studies

Abstract

An efficient and facile In(III)-catalyzed reaction of 3-diazoindolin-2-ones with different arylhydrazines is demonstrated. This approach offers a rapid synthetic route to diversely functionalized 3-arylhydrazonoindolin-2-ones in good yields. This novel protocol...

Evaluation of Anti-Neuroinflammatory Activity of Isatin Derivatives in Activated Microglia

“…HPLC Rt: 25.90 min. 1 H-NMR was in agreement with those reported in the literature [ 31 ]. 1 H-NMR (300 MHz, CDCl 3 ) δ 7.56–7.52 (m, 2H), 6.88–6.83 (m, 1H), 3.71 (t, J = 7.3 Hz, 2H), 1.72–1.62 (m, 2H), 1.46–1.34 (m, 2H), 0.96 (t, J = 7.3 Hz, 3H).…”

“…HPLC Rt: 25.90 min. 1 H-NMR was in agreement with those reported in the literature [31]. 20 (179 mg, 0.84 mmol) was dissolved in pyridine (3.4 mL).…”

Electro-organic synthesis of isatins and hydrazones through C–N cross-coupling and C(sp2)–H/C(sp3)–H functionalization

“…Further, to examine the spectrum of substrates for the synthesis of hydrazones electrochemically, the reactions of hydrazine hydrates with different acetophenone derivatives 4a-l were also investigated, which produced the desired hydrazone derivatives of acetophenones 5a-l in 80-95% yields under the optimized reaction conditions (Scheme 3). 24,25 Various electron-donating groups (methoxy and methyl) were successfully tolerated in this transition, producing good to excellent yields (89-95%). The electron-withdrawing groups such as bromo and nitro also furnished good yields (80-89%) of the respective hydrazone compounds 5a-l (Scheme 3).…”

Visible-light-absorbing C–N cross-coupling for the synthesis of hydrazones involving C(sp2)–H/C(sp3)–H functionalization

“…[24][25][26][27] Hydrazones are an important class of fundamental organic molecules containing C-N bonds that are valuable building blocks for synthesizing biologically active natural products and functional materials. [28][29][30][31][32][33] These hydrazone derivatives have shown a wide range of biological activities, such as anti-proliferative, 34 monoamine oxidase inhibitory, 35 amoebicidal, 36 anti-microbial, 37 insecticidal, 38 anti-inflammatory and analgesic, 39 and EGFR inhibitory. 40 These molecules have also been used in chemical synthesis as dyes, 41 ligands, 42 and fluorescent sensors.…”

“…45 Because of their immense relevance, numerous synthetic methods have been developed to synthesize these hydrazones. 30,31,46,47 Although these techniques for synthesizing hydrazones are often effective, they have one or more drawbacks, such as thermal conditions, metal catalysts, volatile organic solvents, difficulties in product isolation, and unsatisfactory yields. Therefore, it is quite exciting and appealing to establish green, gentle, and effective protocols for visible light-induced C-N coupling using photoredox catalysis.…”