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Synthesis of 4-substituted pyrazole-3,5-diamines via Suzuki–Miyaura coupling and iron-catalyzed reduction

The result's identifiers

  • Result code in IS VaVaI

    <a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61989592%3A15110%2F17%3A73583744" target="_blank" >RIV/61989592:15110/17:73583744 - isvavai.cz</a>

  • Alternative codes found

    RIV/61989592:15310/17:73583744

  • Result on the web

    <a href="http://pubs.rsc.org/en/content/articlepdf/2017/ob/c7ob02373a" target="_blank" >http://pubs.rsc.org/en/content/articlepdf/2017/ob/c7ob02373a</a>

  • DOI - Digital Object Identifier

    <a href="http://dx.doi.org/10.1039/c7ob02373a" target="_blank" >10.1039/c7ob02373a</a>

Alternative languages

  • Result language

    angličtina

  • Original language name

    Synthesis of 4-substituted pyrazole-3,5-diamines via Suzuki–Miyaura coupling and iron-catalyzed reduction

  • Original language description

    A general and efficient synthesis of 4-substituted-1H-pyrazole-3,5-diamines was developed to access derivatives with an aryl, heteroaryl, or styryl group, which are otherwise relatively difficult to prepare. The first step is based on the Suzuki–Miyaura cross-coupling reaction utilizing the XPhos Pd G2 precatalyst. The coupling reactions of 4-bromo-3,5-dinitro-1H-pyrazole with the electron-rich/deficient or sterically demanding boronic acids enabled the production of the corresponding dinitropyrazoles. The subsequent iron-catalyzed reduction of both nitro groups with hydrazine hydrate accomplished the synthesis. The additional demethylation of the 4-methoxystyryl derivative allowed the production of the carboanalog of CAN508 reported as a selective CDK9 inhibitor.

  • 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/LO1304" target="_blank" >LO1304: Support of suistainability of the Institute of Molecular and Translational Medicine</a><br>

  • Continuities

    P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)<br>S - Specificky vyzkum na vysokych skolach

Others

  • Publication year

    2017

  • Confidentiality

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

Data specific for result type

  • Name of the periodical

    Organic &amp; Biomolecular Chemistry

  • ISSN

    1477-0520

  • e-ISSN

  • Volume of the periodical

    15

  • Issue of the periodical within the volume

    48

  • Country of publishing house

    GB - UNITED KINGDOM

  • Number of pages

    12

  • Pages from-to

    10200-10211

  • UT code for WoS article

    000418070800010

  • EID of the result in the Scopus database