A simple, enaminone-based approach to some bicyclic pyridazinium tetrafluoroborates

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216275%3A25310%2F13%3A39896138" target="_blank" >RIV/00216275:25310/13:39896138 - isvavai.cz</a>

Výsledek na webu

<a href="http://dx.doi.org/10.3762/bjoc.9.166" target="_blank" >http://dx.doi.org/10.3762/bjoc.9.166</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.3762/bjoc.9.166" target="_blank" >10.3762/bjoc.9.166</a>

Jazyk výsledku

angličtina

Název v původním jazyce

A simple, enaminone-based approach to some bicyclic pyridazinium tetrafluoroborates

Popis výsledku v původním jazyce

Easily obtainable cyclic enaminones (piperidin-2-ylidenealkanones) can be transformed into substituted bicyclic pyridazinium tetra-fluoroborates upon treatment with corresponding diazonium salts. The transformation can be performed either in a one-pot way or in a two-step process with the isolation of single azo-coupled enaminone as the intermediate. The former method is superior. Under the optimized conditions, a number of pyridazinium salts substituted with both electron-donating and electron-withdrawing substituents was easily synthesized. A mechanism of the formation of the pyridazinium salts is suggested. A partial drawback is the possibility of the formation of a mixture of products when using a different diazonium salt in each step due to a reversibility of the azo coupling. This can be suppressed by using a more reactive diazonium salt before a less reactive one.

Název v anglickém jazyce

A simple, enaminone-based approach to some bicyclic pyridazinium tetrafluoroborates

Popis výsledku anglicky

Easily obtainable cyclic enaminones (piperidin-2-ylidenealkanones) can be transformed into substituted bicyclic pyridazinium tetra-fluoroborates upon treatment with corresponding diazonium salts. The transformation can be performed either in a one-pot way or in a two-step process with the isolation of single azo-coupled enaminone as the intermediate. The former method is superior. Under the optimized conditions, a number of pyridazinium salts substituted with both electron-donating and electron-withdrawing substituents was easily synthesized. A mechanism of the formation of the pyridazinium salts is suggested. A partial drawback is the possibility of the formation of a mixture of products when using a different diazonium salt in each step due to a reversibility of the azo coupling. This can be suppressed by using a more reactive diazonium salt before a less reactive one.

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

S - Specificky vyzkum na vysokych skolach<br>I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Rok uplatnění

2013

Kód důvěrnosti údajů

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

Název periodika

Beilstein Journal of Organic Chemistry

ISSN

1860-5397

e-ISSN

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Svazek periodika

9

Číslo periodika v rámci svazku

neuveden

Stát vydavatele periodika

DE - Spolková republika Německo

Počet stran výsledku

9

Strana od-do

1463-1471

Kód UT WoS článku

000322137200001

EID výsledku v databázi Scopus

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