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Highly Regioselective [3 + 2] Annulation Of Azomethine Imines With 1-alkynyl Fischer Carbene Complexes To Functionalized N,N-bicyclic Pyrazolidin-3-ones.

N. Luo, Zhaoyan Zheng, Z. Yu
Published 2011 · Chemistry, Medicine

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The highly regioselective [3 + 2] cycloaddition of azomethine imines to 1-alkynyl Fischer carbene complexes has been successfully realized under mild conditions. Oxidative demetalation of the newly formed pyrazolo-pyrazolone carbene complexes with pyridine-N-oxide or ceric ammonium nitrate efficiently afforded pyrazolo-pyrazolone derivatives as well as cycloprop-2-enone and trisubstituted 1H-pyrazoles in some cases, providing a novel route to versatile functionalized N,N-bicyclic pyrazolidin-3-ones.
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