α-Thiotetronic Acids, II. Reactions of γ-Alkylidene-α-Thiotetronic Acids

✍ Scribed by Stachel, Hans-Dietrich ;Zeitler, Klaus

• Book ID: 102904227
• Publisher: John Wiley and Sons
• Year: 1995
• Tongue: English
• Weight: 804 KB
• Volume: 1995
• Category: Article
• ISSN: 0947-3440
• DOI: 10.1002/jlac.1995199511282

✦ Synopsis

Abstract

The α‐thiotetronic acid 1 reacts with amines predominantly with ring opening to give polyfunctionalized ketones (2) which readily cyclize to α‐tetramic acid amides (4a, b). The reaction of α‐thiotetronate 6 with nucleophiles is more complex, leading to either an open‐chain derivative (8) or formation of an α‐thiotetronic acid amide (3b) or an α‐tetramate (4f). Treatment of 6 with sodium sulfide in air furnishes the salt of the 1,2‐dithiole 10. The dibrominated α‐thiotetronate 13a reacts with N and S nucleophiles predominantly by substitution, leading finally to the bisthiolactones 14 or the thieno‐1,2‐dithioles 17.