Synthesis and reactions of novel 3-amino-1H,3H-quinoline-2,4-diones

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

Synthesis and reactions of novel 3-amino-1H,3H-quinoline-2,4-diones

Popis výsledku v původním jazyce

Only several title compounds were known till now, no of them with primary amino group. For the synthesis of primary amines, two different strategies were applied: reduction of 3-azido-1H,3H-quinoline-2,4-diones with zinc in acetic acid, and the reactionof 3-chloro-1H,3H-quinoline-2,4-diones with ammonia generated in situ in water-free medium. Secondary amines were conveniently prepared by the aminolysis of 3-chloro- or 3-bromo-1H,3H-quinoline-2,4-diones. Wittig olefination of the title compounds with ethyl (triphenylphosphoranylidene) acetate gave ethyl (2E)-(3-amino-2-oxo-2,3-dihydroquinolin-4(1H)-ylidene)acetates as the major products, accompanied with a small amount of 3,3a-dihydro-5H-pyrrolo[2,3-c]quinoline-2,4-diones. The structure of the pyrrolo[2,3-c]quinoline ring was confirmed by an independent synthesis, via intramolecular Wittig olefination.

Název v anglickém jazyce

Synthesis and reactions of novel 3-amino-1H,3H-quinoline-2,4-diones

Popis výsledku anglicky

Only several title compounds were known till now, no of them with primary amino group. For the synthesis of primary amines, two different strategies were applied: reduction of 3-azido-1H,3H-quinoline-2,4-diones with zinc in acetic acid, and the reactionof 3-chloro-1H,3H-quinoline-2,4-diones with ammonia generated in situ in water-free medium. Secondary amines were conveniently prepared by the aminolysis of 3-chloro- or 3-bromo-1H,3H-quinoline-2,4-diones. Wittig olefination of the title compounds with ethyl (triphenylphosphoranylidene) acetate gave ethyl (2E)-(3-amino-2-oxo-2,3-dihydroquinolin-4(1H)-ylidene)acetates as the major products, accompanied with a small amount of 3,3a-dihydro-5H-pyrrolo[2,3-c]quinoline-2,4-diones. The structure of the pyrrolo[2,3-c]quinoline ring was confirmed by an independent synthesis, via intramolecular Wittig olefination.

Druh

D - Stať ve sborníku

CEP obor

CC - Organická chemie

OECD FORD obor

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Projekt

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Návaznosti

Z - Vyzkumny zamer (s odkazem do CEZ)

Rok uplatnění

2002

Kód důvěrnosti údajů

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

Název statě ve sborníku

20th European Colloquium on Heterocyclic Chemistry - book of abstracts

ISBN

nemá

ISSN

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e-ISSN

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Počet stran výsledku

1

Strana od-do

96

Název nakladatele

Sodertorn University College

Místo vydání

Stockholm

Místo konání akce

Stockholm

Datum konání akce

18. 8. 2002

Typ akce podle státní příslušnosti

EUR - Evropská akce

Kód UT WoS článku

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