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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

  • Czech description

Classification

  • 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

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

  • 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