Traceless Solid-Phase Synthesis of [6,7,8 5,6,7]-Fused Molecular Frameworks

Kód výsledku v 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>

Výsledek na webu

<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>

Jazyk výsledku

angličtina

Název v původním jazyce

Traceless Solid-Phase Synthesis of [6,7,8 5,6,7]-Fused Molecular Frameworks

Popis výsledku v původním jazyce

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.

Název v anglickém jazyce

Traceless Solid-Phase Synthesis of [6,7,8 5,6,7]-Fused Molecular Frameworks

Popis výsledku anglicky

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.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

10401 - Organic chemistry

Projekt

<a href="/cs/project/GA16-06446S" target="_blank" >GA16-06446S: Od aminokyselin k molekulárním skafoldům inspirovaných přírodou</a><br>

Návaznosti

P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)

Rok uplatnění

2018

Kód důvěrnosti údajů

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

Název periodika

MOLECULES

ISSN

1420-3049

e-ISSN

—

Svazek periodika

23

Číslo periodika v rámci svazku

5

Stát vydavatele periodika

CH - Švýcarská konfederace

Počet stran výsledku

12

Strana od-do

"1090-1"-"1090-12"

Kód UT WoS článku

000435204000105

EID výsledku v databázi Scopus

2-s2.0-85046649295