Synthesis of Piperazinones, Piperazines, Tetrahydropyrazines, and Dihydropyrazinones from Polymer-Supported Acyclic Intermediates via N-Alkyl- and N-Acyliminiums

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61989592%3A15310%2F12%3A33141476" target="_blank" >RIV/61989592:15310/12:33141476 - isvavai.cz</a>

Výsledek na webu

<a href="http://dx.doi.org/10.1002/ejoc.201200591" target="_blank" >http://dx.doi.org/10.1002/ejoc.201200591</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1002/ejoc.201200591" target="_blank" >10.1002/ejoc.201200591</a>

Jazyk výsledku

angličtina

Název v původním jazyce

Synthesis of Piperazinones, Piperazines, Tetrahydropyrazines, and Dihydropyrazinones from Polymer-Supported Acyclic Intermediates via N-Alkyl- and N-Acyliminiums

Popis výsledku v původním jazyce

Trisubstituted piperazinones, piperazines, tetrahydropyrazines, and dihydropyrazinones were prepared in a one-step procedure from easily accessible polymer-supported acyclic precursors containing either a masked aldehyde or ketone group. Acid-mediated unmasking of the aldehyde triggered cyclic iminium formation followed by reduction with triethylsilane present in the cleavage cocktail. The effect of the substituent at the iminium-forming nitrogen was evaluated: whereas complete conversion to the targetcompounds was observed with N-alkyl, aryl, and phenylsulfonamido derivatives, the N-acyl compound suffered from a partial reduction of the aldehyde to an alcohol. Similarly, ketones readily provided cyclic iminiums with N-alkyl compounds, whereas their cyclization with N-acyl precursors proceeded unwillingly. Interestingly, cleavage of the resin-bound acyclic precursor at 60 °C in the presence of triethylsilane resulted in the decomposition of the amide bond and formation of a lactone. A

Název v anglickém jazyce

Synthesis of Piperazinones, Piperazines, Tetrahydropyrazines, and Dihydropyrazinones from Polymer-Supported Acyclic Intermediates via N-Alkyl- and N-Acyliminiums

Popis výsledku anglicky

Trisubstituted piperazinones, piperazines, tetrahydropyrazines, and dihydropyrazinones were prepared in a one-step procedure from easily accessible polymer-supported acyclic precursors containing either a masked aldehyde or ketone group. Acid-mediated unmasking of the aldehyde triggered cyclic iminium formation followed by reduction with triethylsilane present in the cleavage cocktail. The effect of the substituent at the iminium-forming nitrogen was evaluated: whereas complete conversion to the targetcompounds was observed with N-alkyl, aryl, and phenylsulfonamido derivatives, the N-acyl compound suffered from a partial reduction of the aldehyde to an alcohol. Similarly, ketones readily provided cyclic iminiums with N-alkyl compounds, whereas their cyclization with N-acyl precursors proceeded unwillingly. Interestingly, cleavage of the resin-bound acyclic precursor at 60 °C in the presence of triethylsilane resulted in the decomposition of the amide bond and formation of a lactone. A

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

<a href="/cs/project/ME09057" target="_blank" >ME09057: Výzkum nových sloučenin s protinádorovou aktivitou za pomoci kombinatoriální chemie</a><br>

Návaznosti

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

Rok uplatnění

2012

Kód důvěrnosti údajů

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

Název periodika

European Journal of Organic Chemistry

ISSN

1434-193X

e-ISSN

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Svazek periodika

N

Číslo periodika v rámci svazku

26

Stát vydavatele periodika

DE - Spolková republika Německo

Počet stran výsledku

10

Strana od-do

5075-5084

Kód UT WoS článku

000308294700026

EID výsledku v databázi Scopus

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