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

Result code in 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>

Alternative codes found

RIV/61989592:15310/18:73591157

Result on the web

<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>

Result language

angličtina

Original language name

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

Original language description

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.

Czech name

—

Czech description

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Type

J_imp - Article in a specialist periodical, which is included in the Web of Science database

CEP classification

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OECD FORD branch

10401 - Organic chemistry

Project

Result was created during the realization of more than one project. More information in the Projects tab.

Continuities

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

Publication year

2018

Confidentiality

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

Name of the periodical

MOLECULES

ISSN

1420-3049

e-ISSN

—

Volume of the periodical

23

Issue of the periodical within the volume

4

Country of publishing house

CH - SWITZERLAND

Number of pages

8

Pages from-to

"976/1"-"976/8"

UT code for WoS article

000434717300268

EID of the result in the Scopus database

2-s2.0-85045927064