New Strategy for the Synthesis of 3,4,5-trisubstituted Isoxazolines from Allyl Compounds

Author(s): Stanislaw Krompiec, Joanna Malarz, Cezary Pietraszuk, Beata Powala, Szymon Rogalski, Jan G. Malecki, Mateusz Penkala, Michal Filapek, Robert Musiol, Josef Jampilek, Marcela Vejsova, Jaroslaw Polanski, Marian Paluch, Sebastian Pawlus, Witold Danikiewicz, Magdalena Kania, Beata Marcol.

Journal Name: Current Organic Chemistry

Volume 18 , Issue 17 , 2014

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Abstract:

A new strategy for the synthesis of trans- and cis + trans-3,4,5-trisubstituted isoxazolines from allyl compounds of QCH2CH=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 QCH2CH=CH2 to (E)-QCH2CH=CHCH2Q 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.

Keywords: 1, 3-Dipolar Cycloaddition, Antifungal agents, High-pressure chemistry, Homogeneous catalysis, Isomerization, Isoxazolines, Metathesis, Regioselectivity.

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Article Details

VOLUME: 18
ISSUE: 17
Year: 2014
Page: [2280 - 2296]
Pages: 17
DOI: 10.2174/1385272819666140912004436
Price: $58

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