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Mononuclear heterocyclic rearrangements. Part 12 . Rearrangement of 1,2,4‐oxadiazoles into indazoles
Author(s) -
Vivoicolò,
Cusmano Giuseppe,
Macaluso Gabriella,
Frenna Vincenzo,
Ruccia Michele
Publication year - 1979
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.5570160434
Subject(s) - chemistry , sequence (biology) , cope rearrangement , sigmatropic reaction , carroll rearrangement , side chain , stereochemistry , oxadiazole , medicinal chemistry , organic chemistry , biochemistry , polymer
The first example of a mononuclear heterocyclic rearrangement involving an XYZ = CCN side‐chain sequence is reported. The 3‐( o ‐aminophenyl)‐, and 3‐( o ‐methylaminophenyl)‐5‐methyl‐1,2,4‐oxadiazoles ( 3a,b ) gave a thermally induced rearrangement into 3‐acylaminoindazoles ( 4a,b ). On the other hand, the 3‐( o ‐acetylaminophenyl)‐5‐methyl‐1,2,4‐oxadiazole ( 3c ) produced a base induced rearrangement into 3‐acetylaminoindazole ( 4a ).