Some Aspects of the Chemistry of Small Ring Organic Molecules: 1-Azetines, 1-Azetidinones, 3-Oxo-β-sultams and Cyclopropenones

Abstract The -lactams and the related -sultams are attractive targets for synthesis because of their central importance in antibiotics such as the penicillins. These heterocycles are of further interest because of their potential as inhibitors of the serine protease class of enzymes, believed to be responsible for diseases such as rheumatoid arthritis and cystic fibrosis. This thesis will describe the synthesis of the 4-vinyl beta lactams (A), thiation of these compounds using Lawesson’s reagent to yield thio lactams (B) and subsequent conversion into the corresponding 1-azetine (C) using Meerwein’s reagent.The -lactams and the related -sultams are attractive targets for synthesis because of their central importance in antibiotics such as the penicillins. These heterocycles are of further interest because of their potential as inhibitors of the serine protease class of enzymes, believed to be responsible for diseases such as rheumatoid arthritis and cystic fibrosis. This thesis will describe the synthesis of the 4-vinyl beta lactams (A), thiation of these compounds using Lawesson’s reagent to yield thio lactams (B) and subsequent conversion into the corresponding 1-azetine (C) using Meerwein’s reagent.