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α‐Thiotetronic Acids, II. Reactions of γ‐Alkylidene‐α‐Thiotetronic Acids
Author(s) -
Stachel HansDietrich,
Zeitler Klaus
Publication year - 1995
Publication title -
liebigs annalen
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0947-3440
DOI - 10.1002/jlac.1995199511282
Subject(s) - chemistry , nucleophile , amide , ring (chemistry) , salt (chemistry) , derivative (finance) , sulfide , sodium salt , medicinal chemistry , organic chemistry , catalysis , inorganic chemistry , financial economics , economics
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 .