Synthesis of Imidazo[2,1-a]isoindolones via Rearrangement and Tandem Cyclization of Amino Acid-based N-Phenacyl-2-cyano-4-nitrobenzensulfonamides

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61989592%3A15310%2F25%3A73632441" target="_blank" >RIV/61989592:15310/25:73632441 - isvavai.cz</a>

Výsledek na webu

<a href="https://pubs.acs.org/doi/pdf/10.1021/acs.joc.4c03113" target="_blank" >https://pubs.acs.org/doi/pdf/10.1021/acs.joc.4c03113</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1021/acs.joc.4c03113" target="_blank" >10.1021/acs.joc.4c03113</a>

Jazyk výsledku

angličtina

Název v původním jazyce

Synthesis of Imidazo[2,1-a]isoindolones via Rearrangement and Tandem Cyclization of Amino Acid-based N-Phenacyl-2-cyano-4-nitrobenzensulfonamides

Popis výsledku v původním jazyce

Esters of amino acids were reacted with 2-cyano-4-nitrobenzenesulfonyl chloride and alkylated with various α-haloketones. The corresponding sulfonamides were heated in a solution of ammonium acetate, which yielded imidazo[2,1-a]isoindolones in one step. The key reaction was based on intramolecular C-arylation followed by spontaneous cycloaddition and cyclocondensation. Two approaches have been developed: (i) solid-phase synthesis starting from amino acids immobilized on Wang resin, which allows rapid preparation of target compounds using the cyclative cleavage strategy, (ii) traditional solution-phase synthesis using amino acids methyl esters as the starting materials. The advantages and drawbacks of both alternatives are compared.

Název v anglickém jazyce

Synthesis of Imidazo[2,1-a]isoindolones via Rearrangement and Tandem Cyclization of Amino Acid-based N-Phenacyl-2-cyano-4-nitrobenzensulfonamides

Popis výsledku anglicky

Esters of amino acids were reacted with 2-cyano-4-nitrobenzenesulfonyl chloride and alkylated with various α-haloketones. The corresponding sulfonamides were heated in a solution of ammonium acetate, which yielded imidazo[2,1-a]isoindolones in one step. The key reaction was based on intramolecular C-arylation followed by spontaneous cycloaddition and cyclocondensation. Two approaches have been developed: (i) solid-phase synthesis starting from amino acids immobilized on Wang resin, which allows rapid preparation of target compounds using the cyclative cleavage strategy, (ii) traditional solution-phase synthesis using amino acids methyl esters as the starting materials. The advantages and drawbacks of both alternatives are compared.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

10401 - Organic chemistry

Projekt

<a href="/cs/project/GA25-16634S" target="_blank" >GA25-16634S: Pteridinové modulátory onkogenní proteinkinas</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

2025

Kód důvěrnosti údajů

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

Název periodika

JOURNAL OF ORGANIC CHEMISTRY

ISSN

0022-3263

e-ISSN

1520-6904

Svazek periodika

90

Číslo periodika v rámci svazku

22

Stát vydavatele periodika

US - Spojené státy americké

Počet stran výsledku

10

Strana od-do

7151-7160

Kód UT WoS článku

001497561800001

EID výsledku v databázi Scopus

2-s2.0-105006681391