ol7b02830_si_002.cif (786.73 kB)
Activation and Substitution of 1‑Ferrocenylalkylamines with Allenones: Application to Three-Component Synthesis of 4‑(1-Ferrocenylalkyl)pyrazoles
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posted on 2017-10-25, 20:48 authored by Zhixiong Chen, Lu Han, Shi-Kai TianA one-pot,
two-step three-component synthesis of 4-(1-ferrocenylalkyl)pyrazoles
has been developed involving activation and substitution of 1-ferrocenylalkylamines
with allenones under mild conditions. A range of 1-ferrocenylalkylamines
reacted with allenones in the presence of dipicolinic acid at room
temperature without extrusion of air and moisture, and the resulting
crude products were treated with hydrazine to afford structurally
diverse 4-(1-ferrocenylalkyl)pyrazoles in moderate to good yields.
Moreover, the three-component reaction was successfully extended to
an enantioenriched α-ferrocenylbenzylamine with complete retention
of configuration.
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presenceApplicationacidretentionThree-ComponentFerrocenylalkylamineActivationmoistureSubstitutioncrudesynthesisactivationAllenone1- ferrocenylalkylaminessubstitutionconfigurationdipicolinicthree-componentextrusionhydrazineenantioenriched α- ferrocenylbenzylamineyieldallenoneFerrocenylone-potSynthesi
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