Synthesis of Imidazo[2,1-a]isoindolones via Rearrangement and Tandem Cyclization of Amino Acid-based N-Phenacyl-2-cyano-4-nitrobenzensulfonamides
The result's identifiers
Result code in 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>
Result on the web
<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>
Alternative languages
Result language
angličtina
Original language name
Synthesis of Imidazo[2,1-a]isoindolones via Rearrangement and Tandem Cyclization of Amino Acid-based N-Phenacyl-2-cyano-4-nitrobenzensulfonamides
Original language description
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.
Czech name
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Czech description
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Classification
Type
J<sub>imp</sub> - 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
Result continuities
Project
<a href="/en/project/GA25-16634S" target="_blank" >GA25-16634S: Pteridine modulators of oncogenic protein kinases</a><br>
Continuities
P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)<br>S - Specificky vyzkum na vysokych skolach
Others
Publication year
2025
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
JOURNAL OF ORGANIC CHEMISTRY
ISSN
0022-3263
e-ISSN
1520-6904
Volume of the periodical
90
Issue of the periodical within the volume
22
Country of publishing house
US - UNITED STATES
Number of pages
10
Pages from-to
7151-7160
UT code for WoS article
001497561800001
EID of the result in the Scopus database
2-s2.0-105006681391