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Reduction products of 3(2 H )‐cinnolinones
Author(s) -
Zey Robert L.
Publication year - 1987
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.5570240505
Subject(s) - chemistry , ammonium hydroxide , zinc , ammonium , medicinal chemistry , oxindole , reduction (mathematics) , stereochemistry , organic chemistry , geometry , mathematics , catalysis
Reduction of 3(2 H )‐cinnolinone with zinc and ammonium hydroxide forms 1,4‐dihydro‐3(2 H )‐cinnolinone which rapidly rearranges to 1‐amino‐2‐indolinone (1‐aminooxindole) in acid solution. 1,4‐Dihydro‐2‐methyl‐3(2 H )‐cinnolinone is formed from 2‐methyl‐3(2 H )‐cinnolinone under the same conditions, but its rearrangement to 1‐( N ‐methylamino)‐2‐indolinone (1‐( N ‐methylamino)oxindole) in acid solution is much slower.