TRANSFORMATION OF 1,2-DITHIOLE-3-THIONES INTO 1,6,6alambda4-TRITHIAPENTALENES via REACTION WITH BROMOETHANONES

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Publikace nespadá pod Ekonomicko-správní fakultu, ale pod Přírodovědeckou fakultu. Oficiální stránka publikace je na webu muni.cz.
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ČMELÍK Richard PAZDERA Pavel

Rok publikování 2006
Druh Článek v odborném periodiku
Časopis / Zdroj Collection of Czechoslovak Chemical Communications
Fakulta / Pracoviště MU

Přírodovědecká fakulta

Citace
Obor Organická chemie
Klíčová slova 1;2-Dithiole-3-thiones; Sulfur heterocycles; Trithiapentalenes; Rearrangements; X-ray diffraction; Reaction mechanism; Heterocyclizations.
Popis We report the reactions of derivatives of 5-amino-3-thioxo-3H-1,2-dithiole-4-carboxylic acid 1 with bromoethanones and acylation agents. Two different routes were used to obtain the products, 3-(acylmethylidene)-3H-1,2-dithioles 4. These compounds were synthesized by acylation of compounds 1 on the amino group, followed by the reaction with bromoethanones and excess of triethylamine. Another method was based on the inverted order of the mentioned reaction steps and in absence of a base. The treatment of 4 with thionyl chloride gave new unsaturated fused lactones 13 whereas thionation led to desired 1,6,6alambda4-trithiapentalenes 5. The structures of products and the reaction mechanisms are discussed.
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