349099-22-5Relevant academic research and scientific papers
Facile access to bicyclic sultams with methyl 1-sulfonylcyclopropane-l- carboxylate moieties
Rassadin, Valentin A.,Tomashevskiy, Aleksandr A.,Sokolov, Viktor V.,Ringe, Arne,Magull, Joerg,De Meijere, Armin
experimental part, p. 2635 - 2641 (2009/11/30)
N-(2,3-Dibromopropyl)- and N-(3,4-dibromobutyl)(methoxycarbonyl) methanesulfanilides upon treatment with potassium carbonate in DMF furnish, methyl 3-aryl-2,2-dioxo-2thia-3-azabicyclo[n.1.0]alkane-1.-carboxylates in yields ranging from 54 to 84% (10 examples). The starting materials were obtained by sulfonylation of N-alkenylanilines with methyl (chlorosulfonyl) acetate and. subsequent bromination. For the N-alkenylanil.in.es (10 examples, 60-77% yield) an efficient new synthesis employing a 2-nitrophenylsulfonyl substituent as a protective as well as an activating group has been developed. The 4-methoxyphenyl (PMP) group could easily be removed, from, the sultam. nitrogen atom by treatment with cerium(IV) ammonium nitrate.
