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Updated: Jun 18, 2025

Preparation of N-2-alkoxyvinylsulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines
Published on: January 3, 2018
Ugi bisamides based on pyrrolyl-β-chlorovinylaldehyde and their unusual transformations
Alexander V Tsygankov1,2, Vladyslav O Vereshchak1,2, Tetiana O Savluk1,2
1Institute of Functional Materials Chemistry, State Scientific Institution "Institute for Single Crystals" of National Academy of Sciences of Ukraine, Nauky Ave., 60, 61072, Kharkiv, Ukraine.
Abstract:
By one-pot four- and three-component Ugi reactions involving convertible isocyanides and unexplored pyrrole-containing β-chlorovinylaldehyde, a small library of 20 bisamides with unusual behavior in post-Ugi transformations was prepared and characterized. Surprisingly, a well-documented approach to obtain peptide-containing carboxylic acids through acid hydrolysis of the convertible isocyanide moiety in the Ugi bisamides proceeded in an unexpected manner in our case, leading to the formation of derivatives of amides of heterylidenepyruvic acid. An optimized synthetic protocol for this transformation was elaborated and a plausible sequence involving the elimination of the 2-chloroacetamide moiety and the conversion of the β-chlorovinyl fragment into a vinyl one is provided.
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