Synthetic Communications p. 3591 - 3597 (2006)
Update date:2022-08-04
Topics:
Valla, Alain
Cartier, Dominique
Zentz, Frederic
Labia, Roger
Easy two-step synthesis of a series of dithiines was performed from succinic anhydride via cyclization of the corresponding 4-(alkylamino)-4- oxobutanoic acids (succinamic acids). The reaction, carried out in polar aprotic solvents, gave 4,8-dithiine-indacene-1,3,5,7-tetraones (diimides 3) via 3,7-bis-4,8-dithia-indacene-1,5-diones (diisoimides 2), which could be isolated. Surprisingly, in this reaction, thionyl chloride appeared as an oxidant, and this process seemed to be useful for the syntheses of S-containing heterocyclic compounds such as 1,4-dithiins. A mechanistic pathway was considered. Copyright Taylor & Francis Group, LLC.
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