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Original article (peer-reviewed)

Journal European Journal of Organic Chemistry
Volume (Issue) 2018(3)
Page(s) 316 - 328
Title of proceedings European Journal of Organic Chemistry
DOI 10.1002/ejoc.v2018.3


The photochem. extrusion of gaseous nitrogen from 2,5-disubstituted tetrazoles to generate reactive nitrilimines in situ represents an efficient and attractive way to form dipoles that can be used to provide useful chems. via 1,3-dipolar cycloaddns.  The concept of "photoclick chem." already inspired numerous researchers, who exploited photochem. processes involving alkenes for the synthesis of adducts or the functionalization of biocompatible materials.  The approach requires bioorthogonality, ease of access to the starting materials and operational simplicity.  The authors report herein the authors' studies toward a photoclick reaction involving 2,5-disubstituted tetrazoles and alkynes as the dipolarophile for the synthesis of pyrazole derivs.  In addn. to the numerous reports recently published on the synthesis of pyrazoles, the authors wish to add to the list a photochem. procedure that represents a mild and atom-economical alternative.  Moreover, considering that such nitrilimines precursors can be accessed in one step from inexpensive and abundant starting materials and given the com. availability of a broad spectrum of alkynes, the authors examd. the scope of the photoclick reaction with respect to reactive partners, enabling the synthesis of a library of useful heteroaroms.