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JOURNAL OF ORGANIC CHEMISTRY · 2024 · IF 3.3

Minisci-Type Dehydrogenative Coupling of N-Heteroaromatic Rings with Inert C(sp3)–H Enabled by a Visible-Light-Catalyzed Intermolecular Hydrogen Atom Transfer Process

Jun-Feng Yang,Yun-Fei Liu,Lin-Lin Wei,Kai-Kai Qiao,Yan-Qiu Zhao,Lei Shi

The Minisci-type dehydrogenative coupling of N-heteroaromatic rings with inert C–H or Si–H partners via visible-light-catalyzed hydrogen atom transfer has been reported. This methodology allows the coupling reactions to be carried out in water as a solvent under air atmospheric conditions with visible-light illumination. A wide range of inert C–H and Si–H partners could be directly coupled with various N-aromatic heterocycles to deliver products in good to excellent yields.

研究领域: 有机化学 · 光化学

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CANADIAN JOURNAL OF CHEMICAL ENGINEERING · 2017 ·Vol. 96 ·期 3 ·679-687 · IF 1.356

Design and scale-up of an alkylated Minisci reaction to produce ethionamide with 4-cyanopyridine as raw materials

Zhongrui Liang,Lichao He,Wenchao Wang,Zhiyong Zhou,Zhongqi Ren

Tuberculosis is a serious bacterial infection in developing countries, especially in areas with drug resistance. The development of the anti-tuberculosis drug ethionamide (ETA) is therefore particularly important. We have designed a new route for ETA synthesis and considered the drug's amenability to large-scale manufacture. We evaluated different routes for the synthesis of ETA and selected the most suitable process for the industrial production of this material, which involved the Minisci reaction of 4-cyanopyridine with propionic acid using a AgNO 3 /(NH 4 ) 2 S 2 O 8 catalyst system under acidic conditions. The effects of different parameters on the reaction were studied, and the production of the intermediate of 2-ethyl-4-cyanopyridine was twice recrystallized from methanol to obtain pure ETA. In the Minisci reaction, the system was stirred for an additional 20 min at 80 °C after the addition of ammonium persulphate solution. The subsequent formation of thioamide was conducted at 40 °C to 60 °C for 1.5 h with a 1:5:2 molar ratio of 4-cyanopyridine, propionic acid, and ammonium sulphide. The purity of the crude ETA reached 98.77 % after two recrystallization steps. This process could be scaled up on a much larger scale (1 kg), leading to the yield of alkylation reaction and overall yield of the production process as 44.06 % and 31.26 %, respectively.

CAS / MDL: 12135-76-1

研究领域: 药物化学 · 有机合成 · 结核病研究

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Minisci-Type Dehydrogenative Coupling of N-Heteroaromatic Rings with Inert C(sp3)–H Enabled by a Visible-Light-Catalyzed Intermolecular Hydrogen Atom Transfer Process

Design and scale-up of an alkylated Minisci reaction to produce ethionamide with 4-cyanopyridine as raw materials