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First iodocyclization reaction of allene–thioureas: an efficient approach to bicyclic β-lactams
Authors:Dinesh R Garud  Amol R Jadhav  Santosh V Lahore  Nilesh M Kahar  Rohini R Joshi  Ramesh A Joshi  Mamoru Koketsu
Institution:1. Department of Chemistry, Sir Parashurambhau College, Sadashiv Peth, Pune 411030, India;2. Division of Organic Chemistry, National Chemical Laboratory, Pune 411008, India;3. Department of Chemistry and Biomolecular Science, Faculty of Engineering, Gifu University, 1-1 Yanagido, Gifu 501-1193, Japan
Abstract:The regioselective iodocyclization reaction of allene–thioureas is described, for the first time, for the synthesis of bicyclic β-lactams. The substitution at the allenyl part heavily influenced the iodocyclization reaction. The iodocyclization reaction of the unsubstituted allene–thioureas afforded six-membered 3-thia-1-dethiacephems whereas, the substituted allene–thiourea afforded seven-membered thiazepines along with five-membered isopenams.
Keywords:β-Lactams  Iodocyclization  Thiourea  Regioselective  Allene
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