Dipolar cycloaddition reactions of organic azides with some acetylenic compounds

Abstract

Phenyl azide 1 and several substituted benzyl azides 2a‐o underwent 1,3‐dipolar cycloaddition reactions with dimethyl acetylenedicarboxylate 3, phenylacetylene 4 and ethyl propiolate 5 to afford the triazoles 6‐13. The reactions of these azides with ethyl propiolate were found to be completely regiospecific.

Studies on the synthesis of a sugar triazole based ligand for protein and DNA binding

“…[25][26][27] Owing to the broad range of applications in biochemical, pharmaceutical, material sciences and biological applications like antibacterial, anti-inammatory, antihypertensive, antifungal, anticancer [28][29][30][31] activities, the 1H-1,2,3 triazoles have attained much attention in synthetic organic chemistry. [32][33][34][35] Similar biological functions were also reported for a variety of bis-triazole compounds. 36 In the past few years, the use of Cu(I) catalyzed azide-alkyne cycloaddition reaction has provided a new insight in the eld of carbohydrate research.…”

Antiaggregating and Antithrombotic Activities of new 1, 2, 3‐Triazolecarboxamides

“…Azides 1 were reacted with ethyl propiolate (2) or ethyl phenylpropiolate (5) in boiling ethanol to give the 1H-1,2,3-triazoles 3/4 or 6/7 (Scheme 1). The products were characterized by 1 H-NMR spectroscopy.…”

“…The most common method for the preparation of 1,2,3-triazoles is the 1,3-dipolar cycloaddition of azides with acetylenes (Scheme 1) [2]. Most of the azides were synthesized according to a procedure reported previously [3].…”

New enantiopure 7-azanorbornane β-substituted prolines by SN2 displacements at the Cγ of the side chain

“…For example, derivative 13 was treated with dimethylacetylenedicarboxylate. 26 The azide underwent 1,3-dipolar cycloaddition very readily to give triazol derivative 17 (Scheme 3) in excellent yield (92%).…”