Truly heterogeneous with retention of its high performance: The 1,3-dipolar cycloaddition of azomethine imines to terminal alkynes was efficiently promoted by the easily prepared, inexpensive, supported copper hydroxide, Cu(OH)x/Al2O3. Various kinds of azomethine imines and terminal alkynes could be utilized as dipoles and dipolarophiles, respectively, to form the corresponding N,N-bicyclic pyrazolidinone derivatives in high yields.
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Yoshimura et al. (2011) studied this question.
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