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Selective and clean synthesis of aminoalkyl-H-phosphinic acids from hypophosphorous acid by phospha-Mannich reaction

The result's identifiers

  • Result code in IS VaVaI

    <a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216208%3A11310%2F20%3A10413846" target="_blank" >RIV/00216208:11310/20:10413846 - isvavai.cz</a>

  • Result on the web

    <a href="https://verso.is.cuni.cz/pub/verso.fpl?fname=obd_publikace_handle&handle=gO5~VBYlSO" target="_blank" >https://verso.is.cuni.cz/pub/verso.fpl?fname=obd_publikace_handle&handle=gO5~VBYlSO</a>

  • DOI - Digital Object Identifier

    <a href="http://dx.doi.org/10.1039/d0ra03075a" target="_blank" >10.1039/d0ra03075a</a>

Alternative languages

  • Result language

    angličtina

  • Original language name

    Selective and clean synthesis of aminoalkyl-H-phosphinic acids from hypophosphorous acid by phospha-Mannich reaction

  • Original language description

    Aminoalkyl-H-phosphinic acids, also called aminoalkylphosphonous acids, are investigated as biologically active analogues of carboxylic amino acids and/or as valuable intermediates for synthesis of other aminoalkylphosphorus acids. Their synthesis has been mostly accomplished by phospha-Mannich reaction of a P-H precursor, an aldehyde and an amine. The reaction is rarely clean and high-yielding. Here, reaction of H(3)PO(2)with secondary amines and formaldehyde in wet AcOH led to aminomethyl-H-phosphinic acids in nearly quantitative yields and with almost no by-products. Surprisingly, the reaction outcome depended on the basicity of the amines. Amines with pK(a)&gt; 7-8 gave the desired products. For less basic amines, reductiveN-methylation coupled with oxidation of H(3)PO(2)to H(3)PO(3)became a relevant side reaction. Primary amines reacted less clearly and amino-bis(methyl-H-phosphinic acids) were obtained only for very basic amines. Reaction yields with higher aldehydes were lower. Unique carboxylic-phosphinic-phosphonic acids as well as poly(H-phosphinic acids) derived from polyamines were obtained. Synthetic usefulness of the aminoalkyl-H-phosphinic was illustrated in P-H bond oxidation and its addition to double bonds, and in selective amine deprotection. Compounds with an ethylene-diamine fragment,e.g.most common polyazamacrocycles, are not suitable substrates. The X-ray solid-state structures of seventeen aminoalkyl-phosphinic acids were determined. In the reaction mechanism,N-hydroxyalkyl species R2NCH2OH and [R2N(CH2OH)(2)](+), probably stabilized as acetate esters, are suggested as the reactive intermediates. This mechanism is an alternative one to the known phospha-Mannich reaction mechanisms. The conditions can be utilized in syntheses of various aminoalkylphosphorus compounds.

  • 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

    10402 - Inorganic and nuclear chemistry

Result continuities

  • Project

    <a href="/en/project/GA19-17380S" target="_blank" >GA19-17380S: Selective Metal Complexation by Polytopic Lligands: Towards Two-Metal Single-Molecule Probes for Biomedical Applications</a><br>

  • Continuities

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

Others

  • Publication year

    2020

  • Confidentiality

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

Data specific for result type

  • Name of the periodical

    RSC Advances

  • ISSN

    2046-2069

  • e-ISSN

  • Volume of the periodical

    10

  • Issue of the periodical within the volume

    36

  • Country of publishing house

    GB - UNITED KINGDOM

  • Number of pages

    21

  • Pages from-to

    21329-21349

  • UT code for WoS article

    000542722900032

  • EID of the result in the Scopus database

    2-s2.0-85086514909