17352-41-9Relevant academic research and scientific papers
Cyclododecanone as a recyclable protecting group for the synthesis of highly functionalized 3-amino-2-thiohydantoins from conventional starting materials
Sathishkumar, Munusamy,Ramachandran, Gunasekar,Sathiyanarayanan, Kulathu Iyer
, p. 8498 - 8501 (2014/03/21)
A simple and efficient approach has been developed for the synthesis of highly substituted 3-amino-2-thiohydantoins using cyclododecanone as a protecting group and thiosemicarbazide, chloroacetic acid and substituted benzaldehyde as reactants. This high yielding (79-96%) protocol is a milder alternative to the traditional method that uses unprotected thiosemicarbazide. It was identified that the preferred pathway is the deprotection of 3-amino-2-thiohydantoins followed by the attack of chloroacetic acid on a secondary nitrogen with subsequent formation of the Knoevenagel product and its reaction with imine leading to the final product. The Royal Society of Chemistry.
