Synthesis of 2-amino-3-arylindoles and their fused analogues via intramolecular C-arylation

Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61989592%3A15310%2F24%3A73626659" target="_blank" >RIV/61989592:15310/24:73626659 - isvavai.cz</a>
Result on the web
<a href="https://onlinelibrary.wiley.com/doi/epdf/10.1002/adsc.202400143" target="_blank" >https://onlinelibrary.wiley.com/doi/epdf/10.1002/adsc.202400143</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1002/adsc.202400143" target="_blank" >10.1002/adsc.202400143</a>

Result language
angličtina
Original language name
Synthesis of 2-amino-3-arylindoles and their fused analogues via intramolecular C-arylation
Original language description
2-Aminobenzyl cyanide was reacted with nitrobenzenesulfonyl chlorides and alkylated under Mitsunobu or Fukuyama conditions. The resulting intermediates were exposed to basic conditions, which triggered a Truce-Smiles rearrangement, leading to intramolecular C-arylation. This reaction was followed by spontaneous cycloaddition, which yielded 2-aminoindole derivatives. The developed synthetic route represents a metal-free approach for accessing 1-substituted 2-amino-3-arylindoles. Furthermore, pyrimido[1,2-a]indoles and 7,8-dihydro-benzo[6,7][1,3]diazepino[4,5-b]indoles were synthesized through the use of functionalized alcohols.
Czech name
—
Czech description
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Type
J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database
CEP classification
—
OECD FORD branch
10401 - Organic chemistry

Project
<a href="/en/project/GA21-06553S" target="_blank" >GA21-06553S: Targeting oncogenic kinases with small molecules</a><br>
Continuities
P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)

Publication year
2024
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

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