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

Coffman Keith C. | Zendy; Duong Vy | Zendy; Bagdasarian Alex L. | Zendy; Fettinger James C. | Zendy; Haddadin Makhluf J. | Zendy; Kurth Mark J. | Zendy

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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.

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