89333-95-9Relevant academic research and scientific papers
1,3-Dipolar Cycloaddition Reactions of Nitrilium Betaines with Aryl Thiocyanates and Selenocyanates
Greig, Derek J.,Hamilton, Douglas G.,McPherson, Michael,Paton, R. Michael,Crosby, John
, p. 607 - 612 (2007/10/02)
The carbon-nitrogen triple bond of aryl thiocyanates acts as a dipolarophile in 1,3-dipolar cycloadditions.Reaction with nitrile oxides, nitrile sulphides, and benzonitrile N-phenylimide yields, respectively, 5-arylthio-1,2,4-oxadiazoles, -thidiazoles and -triazoles.Aryl selenocyanates behave similarly forming 5-arylseleno-1,2,4-oxadiazoles and -thiadiazoles from nitrile oxides and sulphides.Divergent pathways are followed by the reactions of secondary amines such as piperidine with 5-arylthio-1,2,4-oxadiazoles and -thidiazoles, the former yielding 5-piperidyl-1,2,4-oxadiazoles and the latter dihydro-1,2,4-thiadiazole-5-thiones.
1,3-DIPOLAR CYCLOADDITIONS OF NITRILE OXIDES TO ARYL THIOCYANATES: A NEW SYNTHETIC ROUTE TO 5-ARYLTHIO-1,2,4-OXADIAZOLES.
Paton, Michael R.,Hamilton, Douglas G.
, p. 5141 - 5142 (2007/10/02)
Nitrile oxides, generated in situ by thermal dehydrochlorination of hydroximoyl chlorides, undergo 1,3-dipolar cycloaddition to aryl thiocyanates yielding 5-arylthio-1,2,4-oxadiazoles.
