Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 18, Issue 13, Pages 2487-2491Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c9ob02548k
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- National University of Singapore
- Singapore Ministry of Education [WBS R-143-000-669-112]
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A one-pot two-step methodology was exploited to synthesize fused thiazoline-azolium salts via reactions of bromoalkyl-azolium salts with KSCN and NaOH. The synthetic feasibility and versatility was demonstrated by the high yield (>80%) preparation of 13 salts with different backbones, linkers and substituents. Using methylpropionato as an N-protecting group, the resulting salts could be further derivatized to their neutral azole-thiazolines. The reaction sequence proceeds via (i) Br -> SCN substitution, (ii) N-heterocyclic carbene formation, (iii) carbene attack of the S atom and CN- displacement in the alkyl-S-C & xe002;N unit, and (iv) methyl acrylate elimination.
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