Straightforward synthesis of enantiomerically pure 1,2,3-triazoles derived from amino esters

Abstract

A practical and straightforward approach that enables, for the first time, the synthesis of enantiomerically pure 1,4,5-trisubstituted, 1,5-disubstituted, and fused 1,2,3-triazole derivatives has been developed. The synthesis employs enantiomerically pure amino esters derived from amino acids and commercially available ketones under metal-free conditions.

Betulonic acid derivatives inhibiting coronavirus replication in cell culture via the nsp15 endoribonuclease

“…[31][32][33][34] These derivatives were synthesized by our recently developed and convenient "triazolization" method to prepare 1,2,3-triazoles from primary amines and ketones. [35][36][37][38] First, Jones oxidation was performed to convert betulin 1 into betulonic acid 2 (Scheme 1). 39 Betulin 1, a natural compound isolated from the bark of Betula species, is commercially available.…”

Transition‐Metal‐Free Annulation of Enamines and Tosyl Azide toward N‐Heterocycle Fused and 5‐Amino‐1,2,3‐Triazoles

“…Among the splendid progress in the transition metal‐free 1,2,3‐triazole synthesis, the triazole ring formation employing enaminones or analogous stable enamines as key building blocks have been identified as particularly useful and attractive toolkit. Depending on the cleavage of different chemical bonds, highly diverse 1,2,3‐triazoles, including the 1,5‐disbustiuted 1,2,3‐triazoles, N1–H 1,2,3‐triazoles, ester group functionalized 1,2,3‐triazoles, enantiomerically pure 1,2,3‐triazoles, 1,4‐substituted 1,2,3‐triazoles, fully substituted 1,2,3‐triazoles and sulfur side chain functionalized 1,2,3‐triazoles etc have been independently synthesized with efficiency. The successful application of enaminones and analogous enamines in 1,2,3‐triazole synthesis, together with the versatile and featured reactivities of these stable enamines, inspire us that high space remains in the designation of practical synthetic methods toward more diverse 1,2,3‐triazole compounds.…”

A recent overview on the synthesis of 1,4,5-trisubstituted 1,2,3-triazoles

“…compounds. Amino acids, such as tyrosine, ʟ-Phe-ʟ-Phe, glutamic acid, and serine derivatives were proceeded to extend the scope of the reaction (Scheme 13) [44]. 35, amines 36, α-diazo-ß-ketosulfones 37, I 2 , and K 2 CO 3 in EtOH.…”