Synthesis of E,E-bis(chloromethylidene) derivatives of N-organylthiomorpholines and -selenomorpholines and their quaternary salts

Abstract

An efficient method for preparation of hitherto unknown E,E-bis(chloromethylidene) derivatives of -organylthiomorpholines and -selenomorpholines by the reaction of E,E-bis(3-bromo-1-chloro-1-propen-2-yl) sulfide and selenide with primary amines in benzene or THF as well as with ethylammonium bromide in ethanol in the presence of Na₂CO₃ has been described. Heterocylization of the above sulfide and selenide by reaction with diethylamine in THF affords the unknown E,E-bis(chloromethylidene) derivatives of heterocyclic quaternary salts-4,4-diethyl-1,4-thiazinan-4-onium and -1,4-selenazinan-4-onium bromides.

GRAPHICAL ABSTRACT

Keywords:

• E,E-bis(3-bromo-1-chloro-1-propen-2-yl) chalcogenides
• amines
• heterocyclization; -organyl chalcogenomorpholines
• 1,4-chalcogenazinan-4-onium bromides