Six- and seven-membered ring-fused, functionalized cyclopentadienes can be obtained in moderate to excellent yields by a cascade process entailing the Au(I)-catalyzed propargyl Claisen rearrangement/Nazarov cyclization of propargyl vinyl ethers, the hetero-Diels-Alder reaction with dialkylazodicarboxylates, and the spontaneous conversion of cycloaddition products into cyclopentadienes by a highly regioselective cleavage of a C-N bond. Depending on the treatment of the crude reaction mixtures, two types of products can be obtained: cyclopentadienes with pendant hydrazine and aldehyde moieties that intramolecularly react to form hemiaminals are obtained in 43-52% overall yields when the crude reaction mixtures are left over K2CO3 in a DCM solution. Instead, by reducing in situ the aldehyde group just after addition of the heterodienophile, the regioselective C-N bond cleavage generates the corresponding cyclopentadienes bearing a hydrazine and an alcohol appendage in excellent yields (66-82%) over four steps, all in one pot. Two examples from the latter class of compounds were also converted into ring-fused, functionalized cyclopentadienes, bearing a protected amino group, by the selective N-N cleavage of the hydrazine moiety.