Pinacoline Rearrangement of 3,4-Dihydro-3,4-dihydroxyquinolin-2(1H)-ones - an Alternative Pathway to Viridicatin Alkaloids and Their Analogues

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F62690094%3A18470%2F13%3A50001902" target="_blank" >RIV/62690094:18470/13:50001902 - isvavai.cz</a>

Výsledek na webu

<a href="http://dx.doi.org/10.1002/hlca.201300074" target="_blank" >http://dx.doi.org/10.1002/hlca.201300074</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1002/hlca.201300074" target="_blank" >10.1002/hlca.201300074</a>

Jazyk výsledku

angličtina

Název v původním jazyce

Pinacoline Rearrangement of 3,4-Dihydro-3,4-dihydroxyquinolin-2(1H)-ones - an Alternative Pathway to Viridicatin Alkaloids and Their Analogues

Popis výsledku v původním jazyce

3-Alkyl/aryl-3-hydroxyquinoline-2,4-diones were reduced with NaBH4 to give cis-3-alkyl/aryl-3,4-dihydro-3,4-dihydroxyquinolin-2(1H)-ones. These compounds were subjected to pinacol rearrangement by treatment with concentrated H2SO4, resulting in 4-alkyl/aryl-3-hydroxyquinolin-2(1H)-ones. When a benzyl (Bn) group was present in position 3 of the starting compound, its elimination occurred during the rearrangement, and the corresponding 3-hydroxyquinolin-2(1H)-one was formed. The reaction mechanisms are discussed for all transformations. All compounds were characterized by IR, 1H- and 13C-NMR spectroscopy, as well as mass spectrometry.

Název v anglickém jazyce

Pinacoline Rearrangement of 3,4-Dihydro-3,4-dihydroxyquinolin-2(1H)-ones - an Alternative Pathway to Viridicatin Alkaloids and Their Analogues

Popis výsledku anglicky

3-Alkyl/aryl-3-hydroxyquinoline-2,4-diones were reduced with NaBH4 to give cis-3-alkyl/aryl-3,4-dihydro-3,4-dihydroxyquinolin-2(1H)-ones. These compounds were subjected to pinacol rearrangement by treatment with concentrated H2SO4, resulting in 4-alkyl/aryl-3-hydroxyquinolin-2(1H)-ones. When a benzyl (Bn) group was present in position 3 of the starting compound, its elimination occurred during the rearrangement, and the corresponding 3-hydroxyquinolin-2(1H)-one was formed. The reaction mechanisms are discussed for all transformations. All compounds were characterized by IR, 1H- and 13C-NMR spectroscopy, as well as mass spectrometry.

Druh

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

CEP obor

CC - Organická chemie

OECD FORD obor

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Projekt

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Návaznosti

N - Vyzkumna aktivita podporovana z neverejnych zdroju

Rok uplatnění

2013

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

67

Číslo periodika v rámci svazku

10

Stát vydavatele periodika

DE - Spolková republika Německo

Počet stran výsledku

13

Strana od-do

1905-1917

Kód UT WoS článku

000327737700006

EID výsledku v databázi Scopus

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