Formation of fused pyrazoles via intramolecular 1,3-dipolar cycloadditions of diazo intermediates with pendant alkynes are described. A subsequent thermal [1s, 5s] sigmatropic shift of these pyrazole systems resulted in a ring contraction to form spirocyclic pyrazoles. The limitations of this rearrangement were explored by changing the substituents on the non-migrating aromatic ring and by using substrates lacking an aromatic linkage to the propargyl group.