6533b831fe1ef96bd1299717

RESEARCH PRODUCT

Mononuclear heterocyclic rearrangements. Part 12. Rearrangement of 1,2,4-oxadiazoles into indazoles

Nicolò VivonaVincenzo FrennaMichele RucciaGiuseppe CusmanoGabriella Macaluso

subject

StereochemistryChemistryOrganic ChemistryBase (exponentiation)Sequence (medicine)

description

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).

https://doi.org/10.1002/jhet.5570160434