An Expeditious Route for the Synthesis of Oxazepine Triazolo-β-Lactams through Intramolecular Metal-Free [3 + 2] Azide–Alkyne Cycloaddition
Ram N. Yadav
A B , Sunena Chandra B , Armando Paniagua B , Md. Firoj Hossain C and Bimal Krishna Banik B D E
A Department of Chemistry, Faculty of Engineering and Technology, Veer Bahadur Singh Purvanchal University, Jaunpur-222003, Uttar Pradesh, India.
B Department of Chemistry, University of Texas-Pan American, 1201 W. University Dr., Edinburg, TX 78539, USA.
C Department of Chemistry, University of North Bengal, Raja Rammohunpur, Darjeeling-734013, West Bengal, India.
D Department of Mathematics and Natural Sciences, College of Sciences and Human Studies, Deanship of Research, Prince Mohammad Bin Fahd University, Al Khobar 31952, Kingdom of Saudi Arabia.
E Corresponding author. Email: bbanik@pmu.edu.sa
Australian Journal of Chemistry 73(7) 654-657 https://doi.org/10.1071/CH19670
Submitted: 20 January 2020 Accepted: 4 March 2020 Published: 6 May 2020
Abstract
A copper-free intramolecular azide–alkyne cycloaddition reaction of 4-hydroxymethyl-β-lactam with sodium azide has been described. The present approach involves the incorporation of an alkyne moiety through O-alkynylation of 3-hydroxy β-lactam with various propargylic halides. The generality of the method has been demonstrated by treating the corresponding tosylates or mesylates of the hydroxymethyl functionality of a variety of β-lactam-tethered terminal and internal alkynes with sodium azide in a one-pot three-step reaction to furnish novel oxazepane-β-lactam fused triazole scaffolds of diverse interest in good yield.
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