Synthesis of Pyridazine and Pyrrole Analogues of 2-Aminotetralin as Potential Dopaminergics

Syntheses of pyridazine and pyrrole analogues of 2-aminotetralin starting from 3-cyclohexene-1-carboxylic acid are reported. All syntheses involve the following key steps: Curtius rearrangement for amine functionality, inverse electron demand Diels-Alder addition with 1,2,4,5-tetrazine for pyridazine ring synthesis, and pyridazine-to-pyrrole ring contraction for pyrrole ring formation.