Mononuclear heterocyclic rearrangements. Part 12 . Rearrangement of 1,2,4‐oxadiazoles into indazoles | Zendy

Vivoicolò | Zendy; Cusmano Giuseppe | Zendy; Macaluso Gabriella | Zendy; Frenna Vincenzo | Zendy; Ruccia Michele | Zendy

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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 ).

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