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

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

Volume: 18 Issue: 17

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

Affiliation:

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

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.

Cite this article as:

Musiol Robert, Marcol Beata, Kania Magdalena, Danikiewicz Witold, Pawlus Sebastian, Paluch Marian, Polanski Jaroslaw, Vejsova Marcela, Jampilek Josef, Krompiec Stanislaw, Filapek Michal, Penkala Mateusz, Malecki G. Jan, Rogalski Szymon, Powala Beata, Pietraszuk Cezary and Malarz Joanna, New Strategy for the Synthesis of 3,4,5-trisubstituted Isoxazolines from Allyl Compounds, Current Organic Chemistry 2014; 18 (17) . https://dx.doi.org/10.2174/1385272819666140912004436