DABCO-Catalyzed Reaction of 2-Naphthols with Aryl Isothiocyanates: Access to 2-Iminonaphtho-1,3-oxathioles
Thanh Bình Nguyễn, Pascal Retailleau
Abstract
2-Naphthols 1 were found to react with aryl isothiocyanates 2 to provide 2-iminonaphtho-1,3-oxathioles 3 in the presence of DABCO as a catalyst. When elemental sulfur was used, moderate to good yields of 3 could be achieved from a nearly equimolar mixture of two starting materials 1 and 2. Products 3 could also be formed in the absence of sulfur or an external oxidant. In the latter case, an additional equivalent of 2 was found to act as a dehydrogenating agent.
Topics & Concepts
DABCOChemistryCatalysisSulfurArylOrganic chemistryMedicinal chemistryCombinatorial chemistryAlkylSulfur-Based Synthesis TechniquesSynthesis of heterocyclic compoundsChemical Synthesis and Reactions