Direct N1-monosubstitution of piperazine

NĚMEČKOVÁ, Dana a Pavel PAZDERA. Direct N1-monosubstitution of piperazine. In 15th Blue Danube Symposium on Heterocyclic Chemistry. 2013. ISBN 978-80-263-0502-6.

Základní 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: 15th Blue Danube Symposium on Heterocyclic Chemistry, 2013.

Další údaje

• Originální jazyk: čeština
• Typ výsledku: Konferenční abstrakt
• Obor: 10401 Organic chemistry
• Stát vydavatele: Česká republika
• Utajení: není předmětem státního či obchodního tajemství
• Kód RIV: RIV/00216224:14310/13:00074526
• Organizační jednotka: Přírodovědecká fakulta
• ISBN: 978-80-263-0502-6
• 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

Anotace

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.

Anotace 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: Název: Nové katalyzátory a činidla pro udržitelné zelené syntézy a kombinatoriální syntézy.

Investor: Ministerstvo průmyslu a obchodu ČR, Nové katalyzátory a činidla pro udržitelné zelené syntézy a kombinatoriální syntézy