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Tetrahedron. 2017 Jul 20;73(29):4206-4213. doi: 10.1016/j.tet.2016.11.016. Epub 2016 Nov 05.

The intramolecular click reaction using 'carbocontiguous' precursors.

Tetrahedron

Pravin C Patil, Frederick A Luzzio

Affiliations

  1. Department of Chemistry, University of Louisville, 2320 South Brook Street, Louisville, Kentucky 40292 USA.

PMID: 28943665 PMCID: PMC5603183 DOI: 10.1016/j.tet.2016.11.016

Abstract

The synthesis and utilization of all carbon-chain 'carbocontiguous' azidoalkynyl precursors for an intramolecular click reaction is described. The substrates contain both azidoalkyl and ethynylmethyl groups which are conjoined by a 2-(phenylsulfonylmethyl)-4,5-diphenyloxazole lynchpin and are suitably disposed for ring closure. On promotion by copper salts, a number of cyclic click products having the 1,4-disubstituted

Keywords: 1,2,3-triazole; click chemistry; cyclic carbohydrates; cyclic peptides; dipolar cycloaddition

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