About: New Strategy for the Synthesis of 3,4,5-trisubstituted Isoxazolines from Allyl Compounds     Goto   Sponge   NotDistinct   Permalink

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Description
  • A new strategy for the synthesis of trans-and cis + trans-3,4,5-trisubstituted isoxazolines from allyl compounds of QCH(2)CH=CH2 type (Q = PhO, 2,2'-bithiophen-5-yl, BuO, Me3CS, PhN(COMe) and others) has been developed. The dipolarophiles are prepared via: a) Ru-carbene catalysed metathesis of Qallyl; b) catalytic isomerization followed by Ru-carbene mediated metathesis; c) Ru-carbene catalysed metathesis followed by isomerization. 1,3-dipolar cycloaddition of nitrile oxide to dipolarophiles obtained via route a), b) or c), including high pressure activated reactions leads to 3,4,5-trisubstituted isoxazolines. Quantitative E-stereoselective homometathesis of some QCH(2)CH=CH2 to (E)-QCH(2)CH=CHCH(2)Q and new highly effective ruthenium and basic catalytic systems for the isomerization of allyl compounds have also been presented. Moreover, easily available (Z)-XCH2CH=CHCH2X allyl compounds were used for the synthesis of cis-3,4,5-trisubstituted isoxazolines. It has been proved by in vitro tests that some of the isoxazolines show interesting antifungal activity comparable to that of fluconazole.
  • A new strategy for the synthesis of trans-and cis + trans-3,4,5-trisubstituted isoxazolines from allyl compounds of QCH(2)CH=CH2 type (Q = PhO, 2,2'-bithiophen-5-yl, BuO, Me3CS, PhN(COMe) and others) has been developed. The dipolarophiles are prepared via: a) Ru-carbene catalysed metathesis of Qallyl; b) catalytic isomerization followed by Ru-carbene mediated metathesis; c) Ru-carbene catalysed metathesis followed by isomerization. 1,3-dipolar cycloaddition of nitrile oxide to dipolarophiles obtained via route a), b) or c), including high pressure activated reactions leads to 3,4,5-trisubstituted isoxazolines. Quantitative E-stereoselective homometathesis of some QCH(2)CH=CH2 to (E)-QCH(2)CH=CHCH(2)Q and new highly effective ruthenium and basic catalytic systems for the isomerization of allyl compounds have also been presented. Moreover, easily available (Z)-XCH2CH=CHCH2X allyl compounds were used for the synthesis of cis-3,4,5-trisubstituted isoxazolines. It has been proved by in vitro tests that some of the isoxazolines show interesting antifungal activity comparable to that of fluconazole. (en)
Title
  • New Strategy for the Synthesis of 3,4,5-trisubstituted Isoxazolines from Allyl Compounds
  • New Strategy for the Synthesis of 3,4,5-trisubstituted Isoxazolines from Allyl Compounds (en)
skos:prefLabel
  • New Strategy for the Synthesis of 3,4,5-trisubstituted Isoxazolines from Allyl Compounds
  • New Strategy for the Synthesis of 3,4,5-trisubstituted Isoxazolines from Allyl Compounds (en)
skos:notation
  • RIV/00216208:11150/14:10287516!RIV15-MSM-11150___
http://linked.open...avai/riv/aktivita
http://linked.open...avai/riv/aktivity
  • N, V
http://linked.open...iv/cisloPeriodika
  • 17
http://linked.open...vai/riv/dodaniDat
http://linked.open...aciTvurceVysledku
http://linked.open.../riv/druhVysledku
http://linked.open...iv/duvernostUdaju
http://linked.open...titaPredkladatele
http://linked.open...dnocenehoVysledku
  • 32505
http://linked.open...ai/riv/idVysledku
  • RIV/00216208:11150/14:10287516
http://linked.open...riv/jazykVysledku
http://linked.open.../riv/klicovaSlova
  • Regioselectivity; Metathesis; Isoxazolines; Isomerization; Homogeneous catalysis; High-pressure chemistry; Antifungal agents; 3-Dipolar Cycloaddition; 1 (en)
http://linked.open.../riv/klicoveSlovo
http://linked.open...odStatuVydavatele
  • AE - Stát Spojené arabské emiráty
http://linked.open...ontrolniKodProRIV
  • [5348A15C601D]
http://linked.open...i/riv/nazevZdroje
  • Current Organic Chemistry
http://linked.open...in/vavai/riv/obor
http://linked.open...ichTvurcuVysledku
http://linked.open...cetTvurcuVysledku
http://linked.open...UplatneniVysledku
http://linked.open...v/svazekPeriodika
  • 18
http://linked.open...iv/tvurceVysledku
  • Jampílek, Josef
  • Vejsová, Marcela
  • Musiol, Robert
  • Polanski, Jaroslaw
  • Danikiewicz, Witold
  • Filapek, Michal
  • Kania, Magdalena
  • Krompiec, Stanislaw
  • Malarz, Joanna
  • Malecki, Jan G.
  • Marcol, Beata
  • Paluch, Marian
  • Pawlus, Sebastian
  • Penkala, Mateusz
  • Pietraszuk, Cezary
  • Powala, Beata
  • Rogalski, Szymon
http://linked.open...ain/vavai/riv/wos
  • 000344457400009
issn
  • 1385-2728
number of pages
http://localhost/t...ganizacniJednotka
  • 11150
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