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Issue 12, 2019
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Telescoped synthesis of C3-functionalized (E)-arylamidines using Ugi–Mumm and regiospecific quinazolinone rearrangements

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Abstract

An efficient four-step, six-transformation protocol was developed to afford bioactive N-alkyl- or N-arylamide (E)-arylamidines featuring strategic amidine C3 modifications which were inaccessible or low yielding by previous methods. This synthetic approach, exemplified with 24 amidines and requiring only a single purification, highlights a multicomponent Ugi–Mumm rearrangement to afford highly diversified quinazolinones which undergo regiospecific rearrangement to afford new amidines. The method extensively broadens the structural scope of this new class of trisubstituted amidines and demonstrates the tolerance of regional C3 amidine steric bulk, visualized with X-ray crystallographic analysis.

Graphical abstract: Telescoped synthesis of C3-functionalized (E)-arylamidines using Ugi–Mumm and regiospecific quinazolinone rearrangements

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Publication details

The article was received on 10 Jan 2019, accepted on 29 Jan 2019 and first published on 07 Feb 2019


Article type: Paper
DOI: 10.1039/C9OB00073A
Org. Biomol. Chem., 2019,17, 3118-3128

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    Telescoped synthesis of C3-functionalized (E)-arylamidines using Ugi–Mumm and regiospecific quinazolinone rearrangements

    V. A. Jaffett, A. Nerurkar, X. Cao, I. A. Guzei and J. E. Golden, Org. Biomol. Chem., 2019, 17, 3118
    DOI: 10.1039/C9OB00073A

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