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2 article(s) from Kappe, C Oliver

Continuous multistep synthesis of 2-(azidomethyl)oxazoles

Thaís A. Rossa,
Nícolas S. Suveges,
Marcus M. Sá,
David Cantillo and
C. Oliver Kappe

Beilstein J. Org. Chem. 2018, 14, 506–514, doi:10.3762/bjoc.14.36

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Figure 1: Examples of naturally occurring oxazoles (a); some drugs containing oxazole as the active moiety (b...

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Scheme 1: Synthesis of oxazoles 4 by addition of acyl chlorides to azirines 2, as described by Hassner et al. ...

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Scheme 2: Preparation of 2-functionalized oxazoles 7 from 2-(chloromethyl)oxazoles 6 and their application to...

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Scheme 3: Integrated continuous-flow synthesis of 2-(azidomethyl)oxazoles 7.

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Scheme 4: Side products generated during the reaction of azirine 2a with bromoacyl bromide at room temperatur...

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Figure 2: HPLC monitoring of the formation of 2-(azidomethyl)oxazole 7a.

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Figure 3: Continuous sequential thermolysis of vinyl azides 1 and ring expansion of azirines 2 with bromoacet...

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Figure 4: Continuous-flow three-step sequential synthesis of 2-(azidomethyl)oxazoles 7a–c from vinyl azides 1a...

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Published 23 Feb 2018

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Unusual behavior in the reactivity of 5-substituted-1H-tetrazoles in a resistively heated microreactor

Bernhard Gutmann,
Toma N. Glasnov,
Tahseen Razzaq,
Walter Goessler,
Dominique M. Roberge and
C. Oliver Kappe

Beilstein J. Org. Chem. 2011, 7, 503–517, doi:10.3762/bjoc.7.59

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Scheme 1: Azide–nitrile cycloaddition under batch microwave conditions.

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Figure 1: HPLC-UV chromatograms (215 nm) of crude reaction mixtures from the cycloaddition of diphenylacetoni...

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Figure 2: HPLC-UV chromatogram (215 nm) showing the decomposition of tetrazole 2 in NMP/AcOH/H₂O 5:3:2 (0.125...

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Scheme 2: Possible decomposition mechanisms for tetrazole 2 in NMP/AcOH/H₂O.

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Scheme 3: Reaction steps for the degradation of tetrazole 2 and the corresponding rate equations.

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Figure 3: Decomposition of tetrazole 2 at 240 °C in a NMP/AcOH/H₂O 5:3:2 mixture (0.125 M) (points: experimen...

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Figure 4: Decomposition of tetrazole 2 in a 4 mL resistance heated stainless steel coil at a nominal temperat...

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Scheme 4: Mizoroki–Heck coupling under continuous flow conditions.

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Scheme 5: Nucleophilic aromatic substitution of 4-fluoro-1-nitrobenzene (15) with pyrrolidine (16) under cont...

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Figure 5: Nucleophilic aromatic substitution reaction of 1-fluoro-4-nitrobenzene (15) with pyrrolidine (16) i...

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Published 21 Apr 2011

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