Abstract The [3, 3] sigmatropic rearrangement of the allyl ether 2 to provide 3 represents a new synthetic entry into 3, 4-disubstituted β-carbolines. In keeping with the interest in such substituted β-carbolines, the hydrazine mediated conversion of 4-oxo-tetrahydro β-carboline 1b into 4-amino β-carboline 2b is also described, as well as the analogous reaction in the isoquinoline series.