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Journal of Flow Chemistry
Authors: Sara Sadler, Meaghan M. Sebeika, Nicholas L. Kern, David E. Bell, Chloe A. Laverack, Devan J. Wilkins, Alexander R. Moeller, Benjamin C. Nicolaysen, Paige N. Kozlowski, Charlotte Wiles, Robert J. Tinder, and Graham B. Jones

Abstract

A facile and benign route to N-heterocycles, including triazoles and triazolopyrimidines, has been developed. Using continuous-flow microreactor technology, organic azides are prepared in situ and reacted with cyanoacetamide in a [3+2] cycloaddition to produce a variety of substituted 1,2,3-triazoles, which can be elaborated into useful building blocks. A benzyl-substituted triazole was further functionalized to an analog of the core structure of the antiplatelet agent Brilinta®. The methodology lends itself well to flow chemistry, where reaction volumes are minimized, heating and mixing are consistent, and the need for intermediate azide isolation bypassed. The scope of the process is wide, and the efficiency is high, suggesting this as a practical, green route for the production of triazolo-based heterocycles.

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Organic & Biomolecular Chemistry 2015 , 13 , 9528 – 9550 “ Visible-light photoredox catalysis: direct synthesis of fused ¦Â-carbolines through an oxidation/[3 + 2] cycloaddition/oxidative aromatization reaction cascade in batch

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microreactor” R. Munirathinam , R. Ricciardi , R. J. M. Egberink , J. Huskens , M. Holtkamp , H. Wormeester , U. Karst , W. Verboom* Beilstein Journal of Organic Chemistry 2013 , 9 , 1698 – 1704 . “[3 + 2]-Cycloadditions of

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asymmetric synthesis . Tetrahedron Asymmetry . 1998 ; 9 : 2377 – 2407 . 10.1016/S0957-4166(98)00251-1 . 13. Zeng , W , Zhou , YG . Bifunctional AgOAc catalyzed asymmetric [3+2

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