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Issue 16, 2016
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One-pot, regiospecific assembly of (E)-benzamidines from δ- and γ-amino acids via an intramolecular aminoquinazolinone rearrangement

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Abstract

The efficient generation of novel, N-linked benzamidines resulting from a regiospecific rearrangement of quinazolinones is described. This methodology study explored reaction parameters including the effect of changing solvent and temperature, as well as varying electronic substituents on the structural core. The transformation was extensively optimized in terms of reaction conditions and scope, resulting in a protocol that consistently affords diversely functionalized amidines in high yield. The process permits regional structural derivatization that was previously inaccessible, and the multistep process was also reduced to a telescoped, five-step sequence that efficiently affords pharmacologically unique (E)-benzamidoamidines from N-BOC protected γ- and δ-amino acids.

Graphical abstract: One-pot, regiospecific assembly of (E)-benzamidines from δ- and γ-amino acids via an intramolecular aminoquinazolinone rearrangement

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Publication details

The article was received on 18 Nov 2015, accepted on 25 Mar 2016 and first published on 06 Apr 2016


Article type: Paper
DOI: 10.1039/C5OB02378E
Author version available: Download Author version (PDF)
Citation: Org. Biomol. Chem., 2016,14, 3950-3955
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    One-pot, regiospecific assembly of (E)-benzamidines from δ- and γ-amino acids via an intramolecular aminoquinazolinone rearrangement

    C. E. Schroeder, S. A. Neuenswander, T. Yao, J. Aubé and J. E. Golden, Org. Biomol. Chem., 2016, 14, 3950
    DOI: 10.1039/C5OB02378E

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