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Paper | Special issue | Vol 50, No. 2, 1999, pp.713-719
Published online, 1st January, 1970
DOI: 10.3987/COM-98-S(H)61
Formation of Bicyclic β-Lactams from Dichloro-1,4-oxathiane-3-carboxanilides: Nucleophilic Substitution of Nitrogen on Anomeric Carbon

Hoh-Gyu Hahn* and Kee-Hyuk Chang

*Organic Chemistry Laboratory, Korea Institute of Science and Technology, P.O. Box 131, Cheongryang, Seoul 130-650, Korea


Transformation of dichloro-1,4-oxathiane anilides (2) to bicyclic β-lactam (5) is described. In the presence of sodium hydride, an intramolecular nucleophilic substitution of nitrogen to anomeric carbon of 2 gave (1R,6R)-1-chloro-6-methyl-7-phenyl-5-oxa-2-thia-7-azabicyclo[4,2,0]ocata-8-ones (5). The reason for facile displacement at C-2 is attributable to neighboring group participation of sulfur and C-2 is anomeric. Plausible mechanisms for the formation of 2-chloromethyl-5-,6-dihydro-N-phenyl-1,4-oxathiin-3-carboxyamide (4) under the neutral conditions, or 2,3-dihydroxy-2-methyl-N-phenyl-1,4-oxathiane-3-carboxyamide (9) in aqueous solution, or bicyclic β-lactam (5) in the presence of sodium hydride were proposed.