Synthesis of Polycyclic Tetrahydroisoquinolines and Tetrahydrobenzo[d]azepines from Polymer-Supported Allylglycine
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61989592%3A15310%2F22%3A73615674" target="_blank" >RIV/61989592:15310/22:73615674 - isvavai.cz</a>
Result on the web
<a href="https://pubs.acs.org/doi/pdf/10.1021/acs.joc.2c00039" target="_blank" >https://pubs.acs.org/doi/pdf/10.1021/acs.joc.2c00039</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1021/acs.joc.2c00039" target="_blank" >10.1021/acs.joc.2c00039</a>
Alternative languages
Result language
angličtina
Original language name
Synthesis of Polycyclic Tetrahydroisoquinolines and Tetrahydrobenzo[d]azepines from Polymer-Supported Allylglycine
Original language description
Herein, we report a multistep synthesis of polycyclic tetrahydroisoquinolines and tetrahydrobenzo[d]azepines starting from Wang resin-immobilized allylglycine. After sulfonylation with 2/4-nitrobenzenesulfonyl chlorides, Mitsunobu alkylation with various phenylalkynols yielded the corresponding (phenylprop-2-yn-1-yl)-sulfonamides. “Interior” ring-closure enyne metathesis (RCEM) using a Grubbs catalyst 2nd generation (Ru2) yielded functionalized tetrahydroisoquinoline/tetrahydrobenzo[d]azepine intermediates. “East-side” [4+2] cycloaddition with representative dienophiles was followed by the “west-side” construction of different heterocycles using various electrophiles to finally furnish a set of novel molecular frameworks bearing fused [6+6] or [6+7] rings. The developed methodology enables the facile parallel synthesis of novel, pharmacologically promising compounds derived from privileged scaffolds.
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/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)
Others
Publication year
2022
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
87
Issue of the periodical within the volume
8
Country of publishing house
US - UNITED STATES
Number of pages
15
Pages from-to
"5242–5256"
UT code for WoS article
000792258800019
EID of the result in the Scopus database
2-s2.0-85127880196