ol8023727_si_002.pdf (1.6 MB)
Bromoethylsulfonium SaltA More Effective Annulation Agent for the Synthesis of 6- and 7-Membered 1,4-Heterocyclic Compounds
journal contribution
posted on 2009-01-15, 00:00 authored by Muhammad Yar, Eoghan M. McGarrigle, Varinder K. AggarwalReaction of bromoethylsulfonium salt with 1,2-/1,3-aminoalcohols
gave six- and seven-membered rings in good-to-excellent yields. The
reactions proceed through generation of a vinyl sulfonium salt followed
by annulation to give 1,4-heterocyclic compounds such as morpholines
and benzoxazepines in a simple procedure. The method accommodates
a range of nitrogen substituents and the amino alcohol can be substituted
by amino thiols and diamines to give thiomorpholines, piperazines
and benzodiazepines.