1237800-25-7Relevant academic research and scientific papers
Bicyclic sultams with a nitrogen at the bridgehead and a sulfur atom in the apex position: Facile preparation and conformational properties
Rassadin, Valentin A.,Grosheva, Daria S.,Tomashevskiy, Aleksandr A.,Sokolov, Viktor V.,Yufit, Dmitry S.,Kozhushkov, Sergei I.,De Meijere, Armin
, p. 3481 - 3486 (2010)
A practical synthesis of bicyclic sultams with a pyramidal bridgehead nitrogen atom and a sulfur atom in the apex position has been elaborated. Compounds with 1-azathiabicyclo[2.2.1]heptane (12a), -bicyclo[3.2.1]octane (12b, 12d), and -bicyclo[3.3.1]nonane (13b) skeletons were obtained by direct twofold inter/intramolecular alkylation of corresponding monocyclic sultams 9 and 10 with α, ω-dihalides 11 in K2CO3/DMF in 56, 68, 52 and 52% yield, respectively. On the other hand, a 1-aza-9-thiabicyclo[4.2.1] nonane derivative (12c) could be prepared only by stepwise dialkylation in 24 % overall yield. Structural and conformational properties of four of the newly prepared bicyclic sultams in solution as well as in the solid state are discussed.
