Heterocycle-to-heterocycle route to quinoline-4-amines: Reductive heterocyclization of 3-(2-nitrophenyl)isoxazoles

Article abstract of DOI:10.1002/ejoc.201403065

A variety of quinoline-4-amines were synthesized from substituted 3-(2-nitrophenyl)isoxazoles utilizing Zn⁰ or Fe⁰ dust and HOAc using 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.

Full text of DOI:10.1002/ejoc.201403065

Eur. J. Org. Chem. 2014 · © WILEY-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, 2014 · ISSN 1099–0690
SUPPORTING INFORMATION
DOI: 10.1002/ejoc.201403065
Title: Heterocycle-to-Heterocycle Route to Quinoline-4-amines: Reductive Heterocyclization of 3-(2-
Nitrophenyl)isoxazoles
Author(s): Keith C. Coffman, Vy Duong, Alex L. Bagdasarian, James C. Fettinger, Makhluf J. Haddadin, Mark J.
Kurth*

Copies of 1H and 13C NMR spectra of all compounds.
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