[2+2+2] Cyclotrimerization of Alkynes and Isocyanates/Isothiocyanates Catalyzed by Ruthenium–Alkylidene Complexes

Ruthenium carbene catalysts are able to catalyze crossed [2+2+2] cyclotrimerizations of α,ω-diynes with isocyanates, isothiocyanates, and carbon disulfide. Both aliphatic and aromatic isocyanates can be used to produce fused 2-pyridones, although aliphatic isocyanates were more reactive. Aromatic is...

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Bibliographic Details
Published in:Journal of organic chemistry 2013-10, Vol.78 (19), p.9995-10001
Main Authors: Alvarez, Silvia, Medina, Sandra, Domínguez, Gema, Pérez-Castells, Javier
Format: Article
Language:English
Subjects:
Alkynes - chemistry
Catalysis
Coordination Complexes - chemistry
Cyclization
Cycloparaffins - chemistry
Isocyanates - chemistry
Isothiocyanates - chemistry
Ruthenium
Stereoisomerism
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Summary:Ruthenium carbene catalysts are able to catalyze crossed [2+2+2] cyclotrimerizations of α,ω-diynes with isocyanates, isothiocyanates, and carbon disulfide. Both aliphatic and aromatic isocyanates can be used to produce fused 2-pyridones, although aliphatic isocyanates were more reactive. Aromatic isocyanates give better results when they bear electron-donating substituents. The reaction of unsymmetrical α,ω-diynes gave a product only with the substituent adjacent to the 2-pyridone nitrogen. Isothiocyanates gave thiopyranimines upon reaction with the CS bond, whereas CS2 reacted efficiently to give a thioxothiopyrane.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo401538p