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Updated: Jun 14, 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
Multicomponent Synthesis of 3-Thiazolines Using a Modified Asinger-Type Reaction
Vincent R A M Reinartz1, Jordy M Saya1, Darya Hadavi2
1Aachen Maastricht Institute for Biobased Materials (AMIBM), Maastricht University, Urmonderbaan 22, Geleen 6167RD, Netherlands.
None:
The classical Asinger reaction is a four-component process combining sulfur, ammonia, and oxo compounds to access 3-thiazolines, but its efficiency can be hampered by in situ ammonia-derived imine formation. We report a one-pot, two-step modification using preformed trimethylsilyl-imines to efficiently yield the desired 3-thiazolines. This method tolerates a wide range of aromatic aldehydes and α-halocarbonyl compounds under microwave irradiation. Benzothiazole-3-thiazoline products undergo bond isomerization to 2-thiazolines in HFIP under elevated microwave conditions, facilitating the synthesis of (±)-firefly luciferin and related derivatives.
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