Heterocycle-to-Heterocycle Route to Quinoline-4-amines: Reductive Heterocyclization of 3-(2-Nitrophenyl)isoxazoles

Keith C Coffman; Vy Duong; Alex L Bagdasarian; James C Fettinger; Makhlouf J Haddadin; Mark J Kurth

doi:10.1002/ejoc.201403065

Heterocycle-to-Heterocycle Route to Quinoline-4-amines: Reductive Heterocyclization of 3-(2-Nitrophenyl)isoxazoles

European J Org Chem. 2014 Dec;2014(34):7651-7657. doi: 10.1002/ejoc.201403065.

Authors

Keith C Coffman¹, Vy Duong¹, Alex L Bagdasarian¹, James C Fettinger¹, Makhlouf J Haddadin², Mark J Kurth¹

Affiliations

¹ Department of Chemistry, University of California, Davis, One Shields Avenue, Davis, California 95616, http://chemistry.ucdavis.edu/faculty/department_faculty/mark_kurth.html.
² Department of Chemistry, Department American University of Beirut, Institution, Beirut, Lebanon.

Abstract

A variety of quinoline-4-amines were synthesized from substituted 3-(2-nitrophenyl)isoxazoles utilizing Zn⁰ or Fe⁰ dust and HOAc via a reductive heterocyclization process. The starting isoxazoles were synthesized from readily available starting materials. A brief survey of functional groups tolerated in this reductive heterocyclization was performed and several 10-amino-3,4-dihydrobenzo[b][1,6]naphthyridin-1(2H)-one and 9-amino-3,4-dihydroacridin-1(2H)-one examples were synthesized.

Keywords: Diversity Oriented Synthesis; Fused-ring systems; Heterocycle; Heterocyclization; Reduction.

Abstract

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