2014
Direct N1-monosubstitution of piperazine
NĚMEČKOVÁ, Dana a Pavel PAZDERAZákladní údaje
Originální název
Direct N1-monosubstitution of piperazine
Název anglicky
Direct N1-monosubstitution of piperazine
Autoři
NĚMEČKOVÁ, Dana (203 Česká republika, domácí) a Pavel PAZDERA (203 Česká republika, garant, domácí)
Vydání
2nd International Conference on Chemical Technology (ICCT), 2014
Další údaje
Jazyk
čeština
Typ výsledku
Vyžádané přednášky
Obor
10401 Organic chemistry
Stát vydavatele
Česká republika
Utajení
není předmětem státního či obchodního tajemství
Kód RIV
RIV/00216224:14310/14:00088826
Organizační jednotka
Přírodovědecká fakulta
Klíčová slova česky
aza-Michael addition; ionically-bound substrate; metal catalysis; N1-monosubstituted piperazine; piperazine; piperazine-1-ium cation; resin supported metal ion; solid phase synthesis.
Klíčová slova anglicky
aza-Michael addition; ionically-bound substrate; metal catalysis; N1-monosubstituted piperazine; piperazine; piperazine-1-ium cation; resin supported metal ion; solid phase synthesis.
Příznaky
Mezinárodní význam, Recenzováno
Změněno: 26. 2. 2017 13:32, doc. RNDr. Pavel Pazdera, CSc.
V originále
We report new methods for the efficient direct N1-monosubstitution of piperazine based on the reaction of piperazine-1-ium cation with different electrophilic agents optionally under catalysis by various metal ions supported on weakly acidic cation-exchanger resin. Starting piperazine-1-ium was generated in situ from piperazine in acetic acid solution or by chemi-sorption of piperazine on weakly acidic cation-exchanger resin (i. e. solid phase synthesis with ionically bonded substrate). These two methods were used for reaction with electrophilic reagents such as acyl chlorides, anhydrides, sulfonyl chlorides, carbamoyl chlorides, for example. For aza-Michael additions of piperazine-1-ium cation to compounds with an activated multiple carbon-carbon bond (derivatives of acrylic, propiolic and acetylenedicarboxylic acid) this cation was generated in methanol solution by mixing of piperazine with piperazine-1,4-diium dichloride in various proportions. It was found that solid support metal catalysis afforded target products in very good yields under shortening of reaction times.
Anglicky
We report new methods for the efficient direct N1-monosubstitution of piperazine based on the reaction of piperazine-1-ium cation with different electrophilic agents optionally under catalysis by various metal ions supported on weakly acidic cation-exchanger resin. Starting piperazine-1-ium was generated in situ from piperazine in acetic acid solution or by chemi-sorption of piperazine on weakly acidic cation-exchanger resin (i. e. solid phase synthesis with ionically bonded substrate). These two methods were used for reaction with electrophilic reagents such as acyl chlorides, anhydrides, sulfonyl chlorides, carbamoyl chlorides, for example. For aza-Michael additions of piperazine-1-ium cation to compounds with an activated multiple carbon-carbon bond (derivatives of acrylic, propiolic and acetylenedicarboxylic acid) this cation was generated in methanol solution by mixing of piperazine with piperazine-1,4-diium dichloride in various proportions. It was found that solid support metal catalysis afforded target products in very good yields under shortening of reaction times.
Návaznosti
| 2A-1TP1/090, projekt VaV |
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