Syntheses and Configurations of Some Thiomorpholide  S ‐Oxides, Trithiozine Metabolites | Zendy

Farina Carlo | Zendy; Visconti Marco | Zendy; Ventura Paolo | Zendy; Pinza Mario | Zendy; Pifferi Giorgio | Zendy

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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.

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