140667-09-0Relevant articles and documents
Radical Cyclisation in Heterocycle Synthesis. Part 1. Sulfanyl Radical Addition-Cyclisation of Dienylamides for Lactam Synthesis
Naito, Takeaki,Honda, Yuko,Miyata, Okiko,Ninomiya, Ichiya
, p. 19 - 26 (2007/10/02)
A new method for the synthesis of five- to eight-membered lactams by sulfanyl radical mediated-cyclisation of dienylamides is described.The sulfanyl radical addition-cyclisation of the dienylamide 1 was systematically investigated under four different conditions and was found to give the cyclised lactams 2-6 in 54-79percent yield.The stereo- and regio-selectivity of sulfanyl radical addition-cyclisation was established from the preferential formation of the trans-cyclised lactam 3 and also from the substituent effects in the cyclisation of the dienylamides 11-18.The sulfanyl radical mediated addition-cyclisation was successfully applied to the construction of the six- and eight-membered lactams 28a, b.