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Synthesis of bis (1,4-disubstituted-1,2,3 triazoles) starting from diethyl galactarate
Published: 17 November 2022 by MDPI in The 26th International Electronic Conference on Synthetic Organic Chemistry session General Organic Synthesis
This communication reports the synthesis of a series of bis (1,4-disubstituted-1,2,3-triazoles) starting from the known (2,3,4,5) bis acetonide protected diethyl galactarate (1). Reduction of 1 with LiAlH4 led to dioxolane 2 (90%), which upon treatment with CBr4 gave the corresponding dibromide 3 (80%). The reaction of 3 with NaN3 in DMF afforded the key diazide 4 (95%). From diazide 4 were obtained the bis (1,4-disubstituted-1,2,3 triazoles) 5-8 via click reactions with alkyl substituted acetylenes including triphenyltinacetylene. Physical characteristics of the new compounds including selected values1H, 13C, and 119Sn NMR data are given.
Keywords: bis (1,4-disubstituted-1,2,3-triazoles); alkyl and triphenyltin substituents; galactaric framework
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