Synthesis of 1,4-Disubstituted-6-nitro-3,4-dihydro-1H-quinoline-2-ones

X. Wang; S. Dixon; M. J. Kurth; K. S. Lam

doi:10.1055/s-2005-921619

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Synfacts 2005(3): 0354-0354
DOI: 10.1055/s-2005-921619

Polymer-Supported Synthesis

Synthesis of 1,4-Disubstituted-6-nitro-3,4-dihydro-1H-quinoline-2-ones

Contributor(s): Yasuhiro Uozumi, Yoichi M. A. Yamada, Naoshi Fukuyama
X. Wang, S. Dixon, M. J. Kurth, K. S. Lam*
UC-Davis Cancer Center, and Department of Chemistry, UC-Davis, USA

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Publication History

Publication Date:
22 November 2005 (online)

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Significance

A traceless solid-phase synthesis of 1,4-disubstituted-6-nitro-3,4-dihydro-1H-quinazolin-2-ones 3 was developed. N-Alloc-3-amino-3-(2-fluoro-5-nitrophenyl)propionic amide 1 linked to Rink resin was converted into 2 via acylation with R¹CO₂H and ipso-substitution with R²NH₂. The polymeric aniline 2 was treated with 50% HCO₂H/CH₂Cl₂ to release the arylpropionic amide moiety which underwent intramolecular cyclization to form 1,4-disubstituted quinoline 3 in a traceless fashion.