Abstract A divergent strategy for the regioselective and orthogonal synthesis of complementary regioisomers of N-alkyl-3-substituted-tetrahydroindazolones 3 and 4 was achieved from Boc-protected alkylhydrazines 1. The robustness and substrate generality of this method were validated by synthesizing 3 and 4 through the intra-and intermolecular condensation of 1 with various 2-acylcyclohexane-1, 3-diones 2 and aldehydes, ...