Molecular Rearrangement of 9b-Hydroxy-1H-imidazo[4,5-c]quinoline-2,4-diones - A Convenient Pathway to Spiro-Linked Imidazolidine-Oxindole Derivatives

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216275%3A25310%2F09%3A00008303" target="_blank" >RIV/00216275:25310/09:00008303 - isvavai.cz</a>

Nalezeny alternativní kódy

RIV/67985823:_____/09:00328963

Výsledek na webu

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DOI - Digital Object Identifier

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Jazyk výsledku

angličtina

Název v původním jazyce

Molecular Rearrangement of 9b-Hydroxy-1H-imidazo[4,5-c]quinoline-2,4-diones - A Convenient Pathway to Spiro-Linked Imidazolidine-Oxindole Derivatives

Popis výsledku v původním jazyce

The 1-substituted 3-alkyl/aryl-3-aminoquinoine-2,4(1H,3H)-diones 1 react with alkyl/aryl isocynates to give 3-alkyl/aryl-3-ureidoquinoline-2,4(1H,3H)-diones (=N-(3-alkyl/aryl-1,2,3,4-tetrahydro-2,4-dioxoquinolin-3-yl)ureas) 2 and/or 3a-alkyl/aryl-3,3a,5,9b-tetrahydro-9b-hydroxy-1H-imidazo[4,5-c]quinoline -2,4-diones 3 in high yields. Compounds 2 and 3 rearrange by boiling in AcOH or concentrated HCl solution to give three different types of spiro[imidazolidine-4,3'[3H]indole]-2,2'(1'H)-diones, i.e., 10,11, and 12, depending on the kind of substituents at C(3) and C(3a), respectively. All compounds were characterized by H-1- and C-13-NMR and IR spectroscopy as well as by atmospheric-pressure chemical-ionization (APCI) mass spectra. The structures of compounds 11c and 12Al were investigated by single-crystal X-ray diffraction analysis.

Název v anglickém jazyce

Molecular Rearrangement of 9b-Hydroxy-1H-imidazo[4,5-c]quinoline-2,4-diones - A Convenient Pathway to Spiro-Linked Imidazolidine-Oxindole Derivatives

Popis výsledku anglicky

The 1-substituted 3-alkyl/aryl-3-aminoquinoine-2,4(1H,3H)-diones 1 react with alkyl/aryl isocynates to give 3-alkyl/aryl-3-ureidoquinoline-2,4(1H,3H)-diones (=N-(3-alkyl/aryl-1,2,3,4-tetrahydro-2,4-dioxoquinolin-3-yl)ureas) 2 and/or 3a-alkyl/aryl-3,3a,5,9b-tetrahydro-9b-hydroxy-1H-imidazo[4,5-c]quinoline -2,4-diones 3 in high yields. Compounds 2 and 3 rearrange by boiling in AcOH or concentrated HCl solution to give three different types of spiro[imidazolidine-4,3'[3H]indole]-2,2'(1'H)-diones, i.e., 10,11, and 12, depending on the kind of substituents at C(3) and C(3a), respectively. All compounds were characterized by H-1- and C-13-NMR and IR spectroscopy as well as by atmospheric-pressure chemical-ionization (APCI) mass spectra. The structures of compounds 11c and 12Al were investigated by single-crystal X-ray diffraction analysis.

Druh

J_x - Nezařazeno - Článek v odborném periodiku (Jimp, Jsc a Jost)

CEP obor

CA - Anorganická chemie

OECD FORD obor

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Projekt

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Návaznosti

Z - Vyzkumny zamer (s odkazem do CEZ)

Rok uplatnění

2009

Kód důvěrnosti údajů

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

Název periodika

Helvetica Chimica Acta

ISSN

0018-019X

e-ISSN

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Svazek periodika

92

Číslo periodika v rámci svazku

4

Stát vydavatele periodika

CH - Švýcarská konfederace

Počet stran výsledku

19

Strana od-do

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Kód UT WoS článku

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EID výsledku v databázi Scopus

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