Convenient synthesis of thiohydantoins, imidazole-2-thiones and imidazo[2,1-b]thiazol-4-iums from polymer-supported alpha-acylamino ketones

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61989592%3A15110%2F18%3A73591157" target="_blank" >RIV/61989592:15110/18:73591157 - isvavai.cz</a>

Nalezeny alternativní kódy

RIV/61989592:15310/18:73591157

Výsledek na webu

<a href="https://www.mdpi.com/1420-3049/23/4/976/htm" target="_blank" >https://www.mdpi.com/1420-3049/23/4/976/htm</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.3390/molecules23040976" target="_blank" >10.3390/molecules23040976</a>

Jazyk výsledku

angličtina

Název v původním jazyce

Convenient synthesis of thiohydantoins, imidazole-2-thiones and imidazo[2,1-b]thiazol-4-iums from polymer-supported alpha-acylamino ketones

Popis výsledku v původním jazyce

The preparation of 5-methylene-thiohydantoins via solid-phase synthesis is reported in this article. After sulfonylation of immobilized Ser(tBu)-OH with 4-nitrobenzenesulfonyl chloride followed by alkylation with various bromoketones, the 4-Nos group was removed, and the resulting polymer-supported alpha-acylamino ketones were reacted with Fmoc-isothiocyanate. Cleavage of the Fmoc protecting group was followed by the spontaneous cyclative cleavage releasing the 5-methylene-thiohydantoin derivatives from the polymer support. Reduction with triethylsilane (TES) yielded the corresponding 5-methyl-thiohydantoins. When Fmoc-isothiocyanate was replaced with alkyl isothiocyanates, the trifluoroacetic acid (TFA) mediated cleavage from the polymer support was followed by the cyclization reaction and the imidazo[2,1-b]thiazol-4-iums were obtained. Their isomerization conversion in deuterated dimethylsulfoxide led to imidazole-2-thiones.

Název v anglickém jazyce

Convenient synthesis of thiohydantoins, imidazole-2-thiones and imidazo[2,1-b]thiazol-4-iums from polymer-supported alpha-acylamino ketones

Popis výsledku anglicky

The preparation of 5-methylene-thiohydantoins via solid-phase synthesis is reported in this article. After sulfonylation of immobilized Ser(tBu)-OH with 4-nitrobenzenesulfonyl chloride followed by alkylation with various bromoketones, the 4-Nos group was removed, and the resulting polymer-supported alpha-acylamino ketones were reacted with Fmoc-isothiocyanate. Cleavage of the Fmoc protecting group was followed by the spontaneous cyclative cleavage releasing the 5-methylene-thiohydantoin derivatives from the polymer support. Reduction with triethylsilane (TES) yielded the corresponding 5-methyl-thiohydantoins. When Fmoc-isothiocyanate was replaced with alkyl isothiocyanates, the trifluoroacetic acid (TFA) mediated cleavage from the polymer support was followed by the cyclization reaction and the imidazo[2,1-b]thiazol-4-iums were obtained. Their isomerization conversion in deuterated dimethylsulfoxide led to imidazole-2-thiones.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

10401 - Organic chemistry

Projekt

Výsledek vznikl pri realizaci vícero projektů. Více informací v záložce Projekty.

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

MOLECULES

ISSN

1420-3049

e-ISSN

—

Svazek periodika

23

Číslo periodika v rámci svazku

4

Stát vydavatele periodika

CH - Švýcarská konfederace

Počet stran výsledku

8

Strana od-do

"976/1"-"976/8"

Kód UT WoS článku

000434717300268

EID výsledku v databázi Scopus

2-s2.0-85045927064