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Heterocycle‐to‐Heterocycle Route to Quinoline‐4‐amines: Reductive Heterocyclization of 3‐(2‐Nitrophenyl)isoxazoles
Author(s) -
Coffman Keith C.,
Duong Vy,
Bagdasarian Alex L.,
Fettinger James C.,
Haddadin Makhluf J.,
Kurth Mark J.
Publication year - 2014
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201403065
Subject(s) - chemistry , quinoline , combinatorial chemistry , medicinal chemistry , organic chemistry
A variety of quinoline‐4‐amines were synthesized from substituted 3‐(2‐nitrophenyl)isoxazoles utilizing Zn 0 or Fe 0 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(2 H )‐one and 9‐amino‐3,4‐dihydroacridin‐1(2 H )‐one examples were synthesized.