Efficient Synthesis of Taurine and Structurally Diverse Substituted Taurines from Aziridines

Abstract

Taurine and substituted taurines were synthesized efficiently from aziridines via ring-opening reaction with thioacetic acid, oxidation with performic acid, and hydrolysis in hydrochloric acid. The current method shows more benefit in purification and efficiency in the preparation of taurine and structurally diverse 2-substituted, 2,2-disubstituted, and 1,2-, 2,2-, and 2,N-alkylene taurines.

A Versatile Synthesis of Various Substituted Taurines from Vicinal Amino Alcohols and Aziridines

“…We synthesized substituted taur-ines by the ring-opening reaction of aziridines with sodium bisulfite [14] or thioacetic acid followed by peroxyformic acid oxidation and hydrolysis. [15] We also performed a ringopening of episulfides with amine/ammonia followed by peroxyformic acid oxidation to produce these compounds. [16] Enders and co-workers reported an efficient asymmetric synthesis of 2-substituted and 1,2-disubstituted taurine derivatives through aza-Michael addition of enantiopure hydrazines to α,β-unsaturated sulfonates in the presence of Lewis acid catalysts.…”

A Simple Synthesis of Nβ-Fmoc/Z-Amino Alkyl Thiols and their use in the Synthesis of Nβ-Fmoc/Z-Amino Alkyl Sulfonic Acids

“…37 Aziridine ringopening with thioacetic acid leading to the formation of acetyl-b-amino thiols followed by oxidation is also known. 38 Although taurines have been prepared from Boc-and Z-protected compounds, their synthesis using Fmoc-chemistry has yet to be demonstrated. It was envisaged that performic acid oxidation would be a suitable method for the conversion of our thiols into N b -Fmoc/Zamino alkane sulfonic acids (Scheme 3).…”

Recent synthesis of thietanes

“…The treatment of trimethyloxosulfonium iodide (424) with sodium hydride generated dimethyloxosulfonium methylide (426) as the one carbon-containing nucleophile with DMSO (379) as a good leaving group. The nucleophilic attack of 426 on thiiranes 419 from the least substituted ring carbon atom generated the zwitterionic intermediates 427, with a good regioselectivity following the general regioselectivity rule in nucleophilic ring opening reactions of aliphatic three-membered heterocycles [124][125][126][127][128][129][130][131][132]. The generated thiolate in the zwitterionic intermediates 427 then further underwent an intramolecular nucleophilic substitution to yield the desired thietanes 425 by loss of a molecule of DMSO [22] (Scheme 94).…”