1394843-37-8

Basic information

• Product Name: 5,6-ddihydro-4H-pyrrolo[1,2-c][1,2,3]triazole
• Synonyms: 5,6-ddihydro-4H-pyrrolo[1,2-c][1,2,3]triazole
• CAS NO: 1394843-37-8
• Molecular Weight: 109.131
• Mol File: 1394843-37-8.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 5,6-ddihydro-4H-pyrrolo[1,2-c][1,2,3]triazole(CAS DataBase Reference)
• NIST Chemistry Reference: 5,6-ddihydro-4H-pyrrolo[1,2-c][1,2,3]triazole(1394843-37-8)
• EPA Substance Registry System: 5,6-ddihydro-4H-pyrrolo[1,2-c][1,2,3]triazole(1394843-37-8)

Safety Data

• Hazardous Substances Data: 1394843-37-8(Hazardous Substances Data)

Upstream product

• 529-19-1 2-Methylbenzonitrile 
• 199276-58-9 pent-4-ynyl-1-azide 
• 100-47-0 benzonitrile 
• 22364-68-7 2-tolylmethylnitrile 
• 140-29-4 phenylacetonitrile 

Relevant articles and documents

Synthesis of bicyclic imidazoles via [2 + 3] cycloaddition between nitriles and regioselectively generated α-imino gold carbene intermediates

The cyclic α-imino gold carbene intermediate B is most likely generated in situ via regioselective nitrene transfer from an azido group to a tethered terminal alkyne in the presence of a gold catalyst and at ambient temperature. This highly electrophilic intermediate can react with a weakly nucleophilic nitrile, which is used as the reaction solvent, to deliver a bicyclic imidazole rapidly in an overall bimolecular [2 + 2 + 1] cycloaddition and in mostly serviceable yield. The competing intramolecular Huisgen reaction, although likely also catalyzed by gold, is minimized by using AuCl3 as the catalyst.