A Simplified Protocol for Routine Chemoselective Syntheses of Piperazines Substituted In the 1-Position by an Electron Withdrawing Group

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216224%3A14310%2F15%3A00081732" target="_blank" >RIV/00216224:14310/15:00081732 - isvavai.cz</a>

Výsledek na webu

<a href="http://dx.doi.org/10.2174/1570179411666141001232644" target="_blank" >http://dx.doi.org/10.2174/1570179411666141001232644</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.2174/1570179411666141001232644" target="_blank" >10.2174/1570179411666141001232644</a>

Jazyk výsledku

angličtina

Název v původním jazyce

A Simplified Protocol for Routine Chemoselective Syntheses of Piperazines Substituted In the 1-Position by an Electron Withdrawing Group

Popis výsledku v původním jazyce

We report a simplified protocol for the routine direct chemoselective preparation of various piperazines substituted in the 1-position by an electron withdrawing group. These syntheses are based on the reaction of piperazine-1-ium cation with different electrophilic reagents such as acyl chlorides, anhydrides, sulfonyl chlorides, carbamoyl chlorides, and nitrourea as well. Piperazine-1-ium cation was chosen because the reactions of piperazine with electrophilic reagents in different solvents at usual temperatures are not chemoselective and provide mixtures comprising 1-substituted, 1,4-disubstituted and unsubstituted piperazine as well. Simultaneously, the mono-protonation of piperazine is the simplest synthetic method for its protection/deprotection in comparison with the currently used mono-benzylation, mono-Boc-protection, etc.

Název v anglickém jazyce

A Simplified Protocol for Routine Chemoselective Syntheses of Piperazines Substituted In the 1-Position by an Electron Withdrawing Group

Popis výsledku anglicky

We report a simplified protocol for the routine direct chemoselective preparation of various piperazines substituted in the 1-position by an electron withdrawing group. These syntheses are based on the reaction of piperazine-1-ium cation with different electrophilic reagents such as acyl chlorides, anhydrides, sulfonyl chlorides, carbamoyl chlorides, and nitrourea as well. Piperazine-1-ium cation was chosen because the reactions of piperazine with electrophilic reagents in different solvents at usual temperatures are not chemoselective and provide mixtures comprising 1-substituted, 1,4-disubstituted and unsubstituted piperazine as well. Simultaneously, the mono-protonation of piperazine is the simplest synthetic method for its protection/deprotection in comparison with the currently used mono-benzylation, mono-Boc-protection, etc.

Druh

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

CEP obor

CC - Organická chemie

OECD FORD obor

—

Projekt

<a href="/cs/project/2A-1TP1%2F090" target="_blank" >2A-1TP1/090: Nové katalyzátory a činidla pro udržitelné zelené syntézy a kombinatoriální syntézy.</a><br>

Návaznosti

P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)

Rok uplatnění

2015

Kód důvěrnosti údajů

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

Název periodika

Current organic synthesis

ISSN

1570-1794

e-ISSN

—

Svazek periodika

12

Číslo periodika v rámci svazku

2

Stát vydavatele periodika

AE - Spojené arabské emiráty

Počet stran výsledku

7

Strana od-do

173-179

Kód UT WoS článku

000350751700007

EID výsledku v databázi Scopus

—