Synthesis of 2-Thio- and 2-Oxoimidazoles via Cascade Addition−Cycloisomerization Reactions of Propargylcyanamides

Synthesis of 2-Thio- and 2-Oxoimidazoles via Cascade Addition−Cycloisomerization Reactions of Propargylcyanamides

A methodology to generate 2-thio- and 2-oxoimidazoles through an addition−cyclization−isomerization reaction of propargylcyanamides with thiol and alcohol nucleophiles is described. In general, the reaction sequence allows for the rapid formation of highly substituted 2-thio- and 2-oxoimidazoles in...

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Veröffentlicht in:Journal of organic chemistry 2010-01, Vol.75 (1), p.261-264
Hauptverfasser: Giles, Robert L, Nkansah, Richard A, Looper, Ryan E
Format: Artikel
Sprache:eng
Schlagworte:
Alkynes - chemistry
Chemistry
Cyanamide - chemistry
Cyclization
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings
Isomerism
Magnetic Resonance Spectroscopy
Molecular Structure
Organic chemistry
Pargyline - chemistry
Preparations and properties
Structure-Activity Relationship
Sulfhydryl Compounds - chemical synthesis
Sulfhydryl Compounds - chemistry
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Zusammenfassung:A methodology to generate 2-thio- and 2-oxoimidazoles through an addition−cyclization−isomerization reaction of propargylcyanamides with thiol and alcohol nucleophiles is described. In general, the reaction sequence allows for the rapid formation of highly substituted 2-thio- and 2-oxoimidazoles in good to excellent yields.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo902326d