Nitrileimines as an alternative to azides in base-mediated click [3 + 2] cycloaddition with methylene active nitriles

Mykola A Tupychak; Olga Ya Shyyka; Nazariy T Pokhodylo; Mykola D Obushak

doi:10.1039/d0ra01417f

Nitrileimines as an alternative to azides in base-mediated click [3 + 2] cycloaddition with methylene active nitriles

RSC Adv. 2020 Apr 3;10(23):13696-13699. doi: 10.1039/d0ra01417f. eCollection 2020 Apr 1.

Authors

Mykola A Tupychak¹, Olga Ya Shyyka¹, Nazariy T Pokhodylo¹, Mykola D Obushak¹

Affiliation

¹ Department of Organic Chemistry, Ivan Franko National University of Lviv Kyryla i Mefodiya St. 6 Lviv 79005 Ukraine tupychakmykola@gmail.com.

Abstract

Nitrileimines were implemented in practical click protocols with oxopropanenitriles for the straightforward 5-amino-1H-pyrazole synthesis via 1,3-dipolar cycloaddition. The reaction proceeds at room temperature in a short time with base catalysis and no chromatographic purification. High purity products were isolated by simple filtration. The selectivity of the reaction was observed.