I<sub>2</sub>-Promoted [4 + 2] cycloaddition of <i>in situ</i> generated azoalkenes with enaminones: facile and efficient synthesis of 1,4-dihydropyridazines and pyridazines
Jiajun Feng, Tiantong He, Yuxing Xie, Yang Yu, Jonathan B. Baell, Fei Huang
Abstract
A facile and efficient strategy for the synthesis of 1,4-dihydropyridazines and pyridazines through I2-promoted [4 + 2] cycloaddition of in situ generated azoalkenes with enaminones has been developed. The switch in selectivity is attributed to the judicious choice of different reaction temperatures. The key features of this work include controllable and selective synthesis, good functional group tolerance, good to excellent reaction yields, metal/base-free conditions, and also applicability to one-pot methodology.
Topics & Concepts
ChemistryCycloadditionIn situCombinatorial chemistrySelectivityFunctional groupReaction conditionsBase (topology)Organic chemistryCatalysisMathematical analysisPolymerMathematicsSynthesis and Characterization of PyrrolesCyclopropane Reaction MechanismsClick Chemistry and Applications