158554-90-6Relevant academic research and scientific papers
Synthesis and pyrolytic behaviour of thiazolidin-2-one 1,1-dioxides
Aitken, R. Alan,Armstrong, David P.,Galt, Ronald H. B.,Mesher, Shaun T. E.
, p. 2139 - 2145 (2007/10/03)
Four examples of the chiral thiazolidin-2-one 1,1-dioxides 5 have been prepared by reaction of the appropriate amino alcohols 11 with CS2 in aqueous sodium hydroxide to give the thiazolidine-2-thiones 12, followed by oxidation with KMnO4 under phase-transfer conditions in the presence of benzoic acid, either directly or via the thiazolidin-2-ones 13. Upon flash vacuum pyrolysis (FVP) at 650°C, 5a-c decompose mainly by loss of SO2 to give an alkene and benzyl isocyanate together with other products from fragmentation of the N-benzyl group. A significant minor pathway involves net loss of CO2 and water to give the 2-phenyl-4,5-dihydrothiazoles 21 together with their aromatisation products 22 and 23. A mechanism for this new heterocyclic transformation is proposed involving initial expansion to a cyclic carbamic-sulnnic anhydride (2,1,4-oxathiazin-3-one 1-oxide). The fully assigned 13C NMR spectra are presented for 5, 12 and 13 and the 33S NMR spectrum has been obtained for 5c.
Unexpected Thermal Extrusion of CO2 from 3-Benzylthiazolidin-2-one 1,1-Dioxides to Give 2-Phenylthiazolines and Thiazoles
Aitken, R. Alan,Armstrong, David P.,Mesher, Shaun T. E.,Galt, Ronald H. B.
, p. 6143 - 6146 (2007/10/02)
Flash vacuum pyrolysis of a series of chiral 3-benzylthiazolidin-2-one 1,1-dioxides 5, readily prepared from amino acids, results mainly in loss of SO2 to give an alkene and benzyl isocyanate, but a significant minor pathway involves unexpected loss of CO2 and water to give 2-phenylthiazolines 13 and derived thiazoles.
