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Synthesis of 1‐substituted 3‐nitroquinolin‐4(1 H )‐ones
Author(s) -
Radl Stanislav,
Chan KaKong
Publication year - 1994
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570310232
Subject(s) - chemistry , triethyl orthoformate , nucleophile , amine gas treating , medicinal chemistry , combinatorial chemistry , organic chemistry , catalysis
A versatile synthetic method for preparing 1‐substituted 3‐nitroquinolin‐4(1 H )‐ones from corresponding 2‐fluoro‐α‐nitroacetophenones is demonstrated by the synthesis of 6,7‐difluoro derivatives 7a‐c . The method involves sequential treatment of the starting nitroacetophenone with triethyl orthoformate and the appropriate amine, followed by a nucleophilic cyclization reaction under mild conditions. The C‐7 fluorine atom of 7 can be displaced by cyclic amines. Substituted 6‐fluoro‐7‐(4‐methyl‐1‐piperazinyl)‐3‐nitroquinolin‐4(1 H )‐ones 8a‐c were prepared in this way.