Thionation of N-methyl- and N-unsubstituted thiazolidine enaminones | Zendy

Rade Marković | Zendy; Aleksandar Rašović | Zendy; Marija BaranacStojanović | Zendy; Milovan Stojanović | Zendy; Peter J. Steel | Zendy; Stanka Jovetic | Zendy

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Thionation of N-methyl- and N-unsubstituted thiazolidine enaminones

Author(s) -

Rade Marković,

Aleksandar Rašović,

Marija BaranacStojanović,

Milovan Stojanović,

Peter J. Steel,

Stanka Jovetic

Publication year - 2004

Publication title -

journal of the serbian chemical society

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.227

H-Index - 45

eISSN - 1820-7421

pISSN - 0352-5139

DOI - 10.2298/jsc0411909m

Subject(s) - thiazolidine , chemistry , cope rearrangement , stereochemistry , medicinal chemistry

The potential of directional non-bonded 1,5-type S... O interactions to initi- ate the incipient stage of an in situ rearrangement of N-unsubstituted thiazolidine enaminones to functionalized 1,2-dithioles has been demonstrated. The spectral characteristics, as well as X-ray structural analysis of a selected rearranged product, indicate that a dynamic interconversion occurs in solution between the 1,2-dithiole and the 3,3a 4 ,4-trithia-1-azapentalene bicylic form. The lack of the rearrangement in the case of a N-methyl substituted enaminone precursor is attributed to an unfa- vorable methyl migration in the last reaction step.

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