Traceless Solid-Phase Synthesis of [6,7,8 5,6,7]-Fused Molecular Frameworks
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61989592%3A15310%2F18%3A73591224" target="_blank" >RIV/61989592:15310/18:73591224 - isvavai.cz</a>
Result on the web
<a href="https://www.mdpi.com/1420-3049/23/5/1090/htm" target="_blank" >https://www.mdpi.com/1420-3049/23/5/1090/htm</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.3390/molecules23051090" target="_blank" >10.3390/molecules23051090</a>
Alternative languages
Result language
angličtina
Original language name
Traceless Solid-Phase Synthesis of [6,7,8 5,6,7]-Fused Molecular Frameworks
Original language description
We report two synthetic strategies for traceless solid-phase synthesis of molecular scaffolds comprising 6- to 8-membered rings fused with 5- to 7-membered rings. Traceless synthesis facilitated preparation of target molecules without any trace of polymer-supported linkers. The cyclization proceeded via acid-mediated tandem N-acylium ion formation followed by the nucleophilic addition of O- and C-nucleophiles. The presented synthetic strategy enabled, through the use of simple building blocks without any conformational preferences, the evaluation of the predisposition of different combinations of ring sizes to form fused ring molecular scaffolds. Compounds with any combination of [6,7 + 5,6,7] ring sizes were accessible with excellent crude purity. The 8-membered cyclic iminium was successfully fused only with the 5-membered cycle and larger fused ring systems were not formed, probably due to their instability.
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/GA16-06446S" target="_blank" >GA16-06446S: From Amino Acids to Nature-Inspired Molecular Scaffolds</a><br>
Continuities
P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)
Others
Publication year
2018
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
MOLECULES
ISSN
1420-3049
e-ISSN
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Volume of the periodical
23
Issue of the periodical within the volume
5
Country of publishing house
CH - SWITZERLAND
Number of pages
12
Pages from-to
"1090-1"-"1090-12"
UT code for WoS article
000435204000105
EID of the result in the Scopus database
2-s2.0-85046649295