Premium
Synthesis of 2‐aza analog of rosoxacin
Author(s) -
Singh Baldev
Publication year - 1991
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.5570280408
Subject(s) - chemistry , hydrobromic acid , benzonitrile , aniline , derivative (finance) , medicinal chemistry , cyanide , amine gas treating , organic chemistry , financial economics , economics
Abstract Diazotization of 2‐nitro‐4‐(4‐pyridinyl)aniline ( 4 ) in hydrobromic acid gave the corresponding bromo derivative 5 which was treated with cuprous cyanide to give the benzonitrile derivative 6 which in turn was converted to 2‐nitroacetophenone derivative 9 . Reduction of 9 followed by diazotization of the resulting amine 10 gave 7‐(4‐pyridinyl)cinnolin‐4(1 H )‐one ( 11 ) which was subsequently converted to 1 ‐ethyl‐1,4‐dihydro‐4‐oxo‐7‐(4‐pyridinyl)cinnoline‐3‐carboxylic acid ( 14 ) in three steps.