TRANSFORMATION OF 1,2-DITHIOLE-3-THIONES INTO 1,6,6alambda4-TRITHIAPENTALENES via REACTION WITH BROMOETHANONES
| Authors | |
|---|---|
| Year of publication | 2006 |
| Type | Article in Periodical |
| Magazine / Source | Collection of Czechoslovak Chemical Communications |
| MU Faculty or unit | |
| Citation | |
| Field | Organic chemistry |
| Keywords | 1;2-Dithiole-3-thiones; Sulfur heterocycles; Trithiapentalenes; Rearrangements; X-ray diffraction; Reaction mechanism; Heterocyclizations. |
| Description | 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. |
| Related projects: |