An Efficient [3+2] Cycloaddition of para-Quinone Methides with Nitrile Imines to Construct Spiro-pyr

来源 :中国化学会第十六届全国有机合成化学学术研讨会 | 被引量 : 0次 | 上传用户:jners08
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  Spirocyclohexadienones and pyrazolines are prevalent core structures in bioactive molecules1 and natural products.2 On the other hand,spiro compounds have continued to gain attentions in recent years because of their diversified biological activities and pharmacological properties.3 Thus,combining the pyrazolines and cyclohexadienone structural motifs simultaneously into one molecule as spiro-pyrazoline-cyclohexadienones may be significant for drug candidate discovery.4 Herein,we developed an eficient [3+2] cycloaddition of para-quinone methides and nitrile imines to construct spiro-pyrazoline-cyclohexadienones with high regioselectivity.Various p-QMs and nitrile imines bearing electron-donating or electron-withdrawing groups on the phenyl rings were well-tolerated,providing the spiropyrazolines in good to excellent yields.This straightforward protocol for efficient construction of the privileged spiropyrazolines may be further applied in the pharmaceutical industry and make particularly attractive in organic synthesis.
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