Organic Letters 2023, 25, 22, 4028-4032
Base Mediated Rearrangement of α-Dithioacetyl Propargylamines via Expansion of Dithioacetyl Ring: Synthesis of Medium-sized S,S-heterocycles
Mert Dinc, Eda Ismailoglu, Zeynep Mert, Kerem Kaya, Melda Tayanc, Baris Yucel*
ABSTRACT: Base mediated rearrangement of 1,3-dithianyl substituted propargylamines in DMF via expansion of the dithiane ring has been reported. The rearrangement provided 9-membered amino functionalized sulfur-containing heterocycles (dithionine derivatives) in good yields under mild conditions. Propargylamines bearing 5-membered 1,3-dithiolane and 7-membered 1,3-dithiepane rings rearranged in a similar manner yielding 8- and 10-membered S,S- heterocycles, respectively.