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Synthesis 1987; 1987(5): 456-460
DOI: 10.1055/s-1987-33432
DOI: 10.1055/s-1987-33432
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Die Synthese von 2H-Thiopyranen aus ß-Thioxoaldehyden
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Publication History
Publication Date:
18 September 2002 (online)
The Synthesis of 2H-Thiopyranes from ß-Thioxoaldehydes [4+2]-Cycloaddition reactions between enaminothioketones and activated alkenes, which are described by Quiniou et al.,1-4 usually require relatively harsh reaction conditions, and produce the title compounds only in moderate yields. Much better results can be achieved by a new synthesis of 3-acyl-2H-thiopyranes starting with dicyclohexylammonium salts of monothio-ß-dicarbonyl compounds and unsaturated aldehydes or ketones. The mechanism of this new reaction is characterized by Michael addition followed by an aldol reaction.