Facile Synthesis of 2-Methylnicotinonitrile through Degenerate Ring Transformation of Pyridinium Salts

Duan, Xiaoxia; Sun, Rui; Tang, Juan; Li, Shun; Xiao, Yang; Zheng, Xueli; Li, Ruixiang; Chen, Hua; Fu, Haiyan

doi:10.1021/acs.joc.2c00614

Cited by 3 publications

(1 citation statement)

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“…Subsequently, Trofimov reported the cyclization of available acylethynylpyrroles with acetonitrile to provide a series of pyrrolyl-pyridines in 63-87% yields [60]. In 2022, Duan et al reported a new strategy for the synthesis of 2-methylnicotinonitriles 74 through the degenerate ring transformation of N-substituted pyridinium salts 73 (Scheme 18) [61]. The reaction was carried out using potassium hexamethyldisilazide (KHMDS), benzoic acid (BA), and benzyl triethyl ammonium chloride (TEBA) as additives in acetonitrile at 90 • C for 20 h. This reaction is applicable to various phenyl-substituted 4-phenyl-1-vinylpyridin-1-ium tetrafluoroborates and 3-aryl pyridinium salts, while 4-alkyl-substituted pyridinium salts are limited.…”

Section: Synthesis Of 3-cyanopyridinementioning

confidence: 99%

Advances in the Application of Acetonitrile in Organic Synthesis since 2018

Zhong

Zhang²,

Luo

et al. 2023

Catalysts

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Acetonitrile is commonly used as an organic solvent and can also be used as an important intermediate in organic synthesis. Its widespread use has led to the development of new methods for the synthesis of a variety of important compounds. In the past decades, the conversion reactions of acetonitrile as a building block have become one of the most-attractive fields in organic synthesis. Especially in the field of electrochemical conversions involving acetonitrile, due to its good conductivity and environmentally friendly features, it has become a powerful and compelling tool to afford nitrogen-containing compounds or nitrile-containing compounds. In this review, we mainly discuss the research progress involving acetonitrile in the past five years, covering both conventional synthesis methods and electrochemical synthesis. Besides, a detailed discussion of the substrate scope and mechanistic pathways is provided.

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Section: Synthesis Of 3-cyanopyridinementioning

confidence: 99%

Advances in the Application of Acetonitrile in Organic Synthesis since 2018

Zhong

Zhang²,

Luo

et al. 2023

Catalysts

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One-Pot Knoevenagel/Imination/6π-Azaelectrocyclization Sequence for the Synthesis of Disubstituted Nicotinonitriles

et al. 2023

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We report on a copper-catalyzed three-component reaction for the synthesis of disubstituted nicotinonitriles using 3bromopropenals, benzoylacetonitriles, and ammonium acetate (NH 4 OAc). The Knoevenagel-type condensation of 3bromopropenals with benzoylacetonitriles gives δ-bromo-2,4-dienones that contain strategically placed functional groups that react with the ammonia generated in situ to give the corresponding azatrienes. These azatrienes can then be transformed into trisubstituted pyridines under the reaction conditions via a reaction sequence involving 6π-azaelectrocyclization and aromatization.

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