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Issue 13, 2014
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Highly facile and regio-selective synthesis of pyrazolo[1,5-a]pyrimidines via reactions of 1,2-allenic ketones with aminopyrazoles

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Abstract

An efficient procedure for the syntheses of pyrazolo[1,5-a]pyrimidines through reactions of 1,2-allenic ketones with aminopyrazoles under extremely mild conditions without using any catalyst or promoter has been developed. The reactions showed excellent regio-selectivity with all the allenic ketone substrates except for those bearing an alkyl group at the internal position of the allene moiety. The reason behind this regio-selectivity dissimilarity has been explored with the aid of the B3LYP/6-31G* level of density functional theory. Moreover, this novel procedure has been successfully applied in the preparation of nucleoside-pyrazolo[1,5-a]pyrimidine chimeras with potent antiviral activities.

Graphical abstract: Highly facile and regio-selective synthesis of pyrazolo[1,5-a]pyrimidines via reactions of 1,2-allenic ketones with aminopyrazoles

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Article information


Submitted
06 Dec 2013
Accepted
23 Jan 2014
First published
24 Jan 2014

Org. Biomol. Chem., 2014,12, 2099-2107
Article type
Paper

Highly facile and regio-selective synthesis of pyrazolo[1,5-a]pyrimidines via reactions of 1,2-allenic ketones with aminopyrazoles

X. Zhang, Y. Song, L. Gao, X. Guo and X. Fan, Org. Biomol. Chem., 2014, 12, 2099
DOI: 10.1039/C3OB42445F

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