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Eschenmoser coupling reactions starting from primary thioamides. When do they work and when not?
Authors: Marek Lukáš | Váňa Jiří | Svoboda Jan | Hanusek Jiří
Year: 2023
Type of publication: článek v odborném periodiku
Name of source: Beilstein Journal of Organic Chemistry
Publisher name: Beilstein-Institut
Place: Frankfurt am Main
Page from-to: 808-819
Titles:
Language Name Abstract Keywords
cze Eschenmoserovy kopulační reakce vycházející z primárních thioamidů. Kdy fungují a kdy ne? Byly zkoumány reakce thiobenzamidu nebo thioacetamidu s 4-brom-1,1-dimethyl-1,4-dihydroisochinolin-3(2H)-onem, 4-bromisochinolin-1,3(2H,4H)-dionem a dvěma alfa-brom(fenyl)acetamidy za různých podmínek (báze, rozpouštědlo, thiofil, teplota). Dále byly identifikovány faktory jako např. vlastnosti struktury/média, které ovlivňují distribuci produktu (Eschenmoserova kopulační reakce, Hantzschova syntéza thiazolu a eliminace na nitrily). Klíčovým faktorem pro úspěšnou Eschenmoserovu reakci je acidita intermediární α-thioiminiové soli na atomech dusíku a α-uhlíku. Eschenmoserova kopulační reakce; Hantzschova syntéza thiazolů; isochinolin-4-ony; primární thioamidy; vztahy struktura-reaktivita
eng Eschenmoser coupling reactions starting from primary thioamides. When do they work and when not? Reactions of thiobenzamide or thioacetamide with 4-bromo-1,1-dimethyl-1,4-dihydroisoquinoline-3(2H)-one, 4-bromoisoquino-line-1,3(2H,4H)-dione and two alpha-bromo(phenyl)acetamides were examined under various conditions (base, solvent, thiophile, tem-perature) and structure/medium features that influence product distribution (Eschenmoser coupling reaction, Hantzsch thiazole syn-thesis and elimination to nitriles) were identified. The key factor that enables the successful Eschenmoser coupling reaction involves the optimum balance in acidity of nitrogen and carbon atoms of the intermediary alpha-thioiminium salts. Eschenmoser coupling reaction; Hantzsch thiazole synthesis; isoquinolin-4-ones; primary thioamides; structure-reactivity relationships

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