Transformation of 3-Thiocyanatoquinoline-2,4-diones in a Strong Acidic Medium

Kód výsledku v IS VaVaI

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Výsledek na webu

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DOI - Digital Object Identifier

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Jazyk výsledku

angličtina

Název v původním jazyce

Transformation of 3-Thiocyanatoquinoline-2,4-diones in a Strong Acidic Medium

Popis výsledku v původním jazyce

3-Thiocyanatoquinolone-2,4-diones 2, accessible by thiocyanation of 4-hydroxy-2-quinolones, are highly sensitive towards water. However, their conversion to compounds 3 and 4 can be carried out in 96% sulfuric acid. In the presence of excess of phosphorus pentoxide, C-dealkylated compound 5 (R1 =H) was obtained from 2 (R1 = H, R2 = Bu). Inasmuch as compounds 4 can be smoothly converted to valuable compounds 7 and 8 and compounds 5 are hardly obtainable from 3-unsubstituted 2-quinolones, we decided to study the reaction of compounds 2 in detail. The influence of the type of substitution at positions 1 and 4 in 2, composition of the reaction mixture and its processing, and the reaction time on the yield of individual products 3-5 and also on lately isolated compounds 6 was studied. The results will be discussed and the reaction mechanism will be proposed.

Název v anglickém jazyce

Transformation of 3-Thiocyanatoquinoline-2,4-diones in a Strong Acidic Medium

Popis výsledku anglicky

3-Thiocyanatoquinolone-2,4-diones 2, accessible by thiocyanation of 4-hydroxy-2-quinolones, are highly sensitive towards water. However, their conversion to compounds 3 and 4 can be carried out in 96% sulfuric acid. In the presence of excess of phosphorus pentoxide, C-dealkylated compound 5 (R1 =H) was obtained from 2 (R1 = H, R2 = Bu). Inasmuch as compounds 4 can be smoothly converted to valuable compounds 7 and 8 and compounds 5 are hardly obtainable from 3-unsubstituted 2-quinolones, we decided to study the reaction of compounds 2 in detail. The influence of the type of substitution at positions 1 and 4 in 2, composition of the reaction mixture and its processing, and the reaction time on the yield of individual products 3-5 and also on lately isolated compounds 6 was studied. The results will be discussed and the reaction mechanism will be proposed.

Druh

O - Ostatní výsledky

CEP obor

CC - Organická chemie

OECD FORD obor

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Projekt

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Návaznosti

S - Specificky vyzkum na vysokych skolach

Rok uplatnění

2011

Kód důvěrnosti údajů

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů