Synthesis of 2-Alkylsulfonyl-imidazoles with Three Diversity Positions from Immobilized alpha-Acylamino Ketones

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61989592%3A15110%2F18%3A73591187" target="_blank" >RIV/61989592:15110/18:73591187 - isvavai.cz</a>

Nalezeny alternativní kódy

RIV/61989592:15310/18:73591187

Výsledek na webu

<a href="https://pubs.acs.org/doi/pdf/10.1021/acscombsci.8b00075" target="_blank" >https://pubs.acs.org/doi/pdf/10.1021/acscombsci.8b00075</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1021/acscombsci.8b00075" target="_blank" >10.1021/acscombsci.8b00075</a>

Jazyk výsledku

angličtina

Název v původním jazyce

Synthesis of 2-Alkylsulfonyl-imidazoles with Three Diversity Positions from Immobilized alpha-Acylamino Ketones

Popis výsledku v původním jazyce

The synthesis of novel imidazole derivatives via immobilized alpha-acylamino ketones is reported in this article. The key intermediates were prepared from the Wang-piperazine resin-supported Fmoc-amino acids. After their sulfonylation with 4-nitrobenzenesulfonyl chloride (4-Nos-Cl) followed by alkylation with alpha-bromoketones and cleavage of Nos group, the resulting alpha-acylamino ketones were reacted with Fmoc-isothiocyanate. The corresponding Fmoc-thioureas were subjected to the Fmoc-cleavage and spontaneous ring-closure to imidazole scaffold. The resulting imidazole-thiones were alkylated with alkyl halides and oxidized using meta-chloroperbenzoic acid (mCPBA). Trifluoroacetic acid (TFA)-mediated cleavage yielded the corresponding trisubstituted 2-alkylsulfonyl imidazoles in good crude purity and acceptable overall yields. In the case of sulfides, prepared from alkyl bromides, the unexpected products brominated at the C4 position of the imidazole were obtained.

Název v anglickém jazyce

Synthesis of 2-Alkylsulfonyl-imidazoles with Three Diversity Positions from Immobilized alpha-Acylamino Ketones

Popis výsledku anglicky

The synthesis of novel imidazole derivatives via immobilized alpha-acylamino ketones is reported in this article. The key intermediates were prepared from the Wang-piperazine resin-supported Fmoc-amino acids. After their sulfonylation with 4-nitrobenzenesulfonyl chloride (4-Nos-Cl) followed by alkylation with alpha-bromoketones and cleavage of Nos group, the resulting alpha-acylamino ketones were reacted with Fmoc-isothiocyanate. The corresponding Fmoc-thioureas were subjected to the Fmoc-cleavage and spontaneous ring-closure to imidazole scaffold. The resulting imidazole-thiones were alkylated with alkyl halides and oxidized using meta-chloroperbenzoic acid (mCPBA). Trifluoroacetic acid (TFA)-mediated cleavage yielded the corresponding trisubstituted 2-alkylsulfonyl imidazoles in good crude purity and acceptable overall yields. In the case of sulfides, prepared from alkyl bromides, the unexpected products brominated at the C4 position of the imidazole were obtained.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

10401 - Organic chemistry

Projekt

<a href="/cs/project/LO1304" target="_blank" >LO1304: Podpora udržitelnosti Ústavu molekulární a translační medicíny</a><br>

Návaznosti

P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)<br>S - Specificky vyzkum na vysokych skolach

Rok uplatnění

2018

Kód důvěrnosti údajů

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

Název periodika

ACS Combinatorial Science

ISSN

2156-8952

e-ISSN

—

Svazek periodika

20

Číslo periodika v rámci svazku

8

Stát vydavatele periodika

US - Spojené státy americké

Počet stran výsledku

5

Strana od-do

467-471

Kód UT WoS článku

000441852300001

EID výsledku v databázi Scopus

2-s2.0-85049615245