Premium
Syntheses and Configurations of Some Thiomorpholide S ‐Oxides, Trithiozine Metabolites
Author(s) -
Farina Carlo,
Visconti Marco,
Ventura Paolo,
Pinza Mario,
Pifferi Giorgio
Publication year - 1981
Publication title -
archiv der pharmazie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.468
H-Index - 61
eISSN - 1521-4184
pISSN - 0365-6233
DOI - 10.1002/ardp.19813141108
Subject(s) - morpholine , chemistry , reagent , stereochemistry , oxide , medicinal chemistry , combinatorial chemistry , organic chemistry
Two metabolites of trithiozine, namely 4‐(3,5‐dimethoxy‐4‐hydroxythiobenzoyl)morpholine S ‐oxide (2a) and 4‐(3,4,5‐trimethoxythiobenzoyl)morpholine S ‐oxide (2b) , were synthesized by oxidation of the thioamides 1a, b or, in the case of 2b , by reaction of E ‐ and Z ‐(3,4,5‐trimethoxyphenyl)(methylthio)sulfine (4) with morpholine. Both procedures afford the compounds 2a, b as single isomers having the same configuration at the sulfine group. The NMR behaviour of the aromatic ortho protons of 2b , when compared to that of other aromatic sulfines with known structures in the presence of lanthanide shift reagents, supports the Z ‐configuration.