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Hetaryl Thioketones: Synthesis and Selected Reactions


Mloston, Grzegorz; Urbaniak, Katarzyna; Gebicki, Krzystof; Grzelak, Paulina; Heimgartner, Heinz (2014). Hetaryl Thioketones: Synthesis and Selected Reactions. Heteroatom Chemistry, 25(6):548-555.

Abstract

A series of phenyl/hetaryl and bishetaryl thioketones have been prepared via oxygen/sulfur exchange of the corresponding ketones by treatment with Lawesson’s reagent. The nonsymmetrical ketones were conveniently accessible via the reactions of lithiated furan, thiophene, and selenophene with N,N-dimethylbenzamide and hetarylcarboxamides, respectively, whereas the symmetrical ketones were obtained by treatment of ethyl N,N-dimethylcarbamate with 2 equiv of lithiated heterocycles. Under typical conditions, selected examples of the hetaryl thioketones were oxidized selectively to give thiocarbonyl S-oxides (sulfines). Reactions with diazomethane at –65°C yielded 1,3-dithiolanes in a regioselective manner and hetero-Diels–Alder reactions of 2-thienyl substituted thioketones with dimethyl acetylenedicarboxylate yielded the corresponding 7H-thieno[2,3- c]thiopyran-4,5-dicarboxylates.

Abstract

A series of phenyl/hetaryl and bishetaryl thioketones have been prepared via oxygen/sulfur exchange of the corresponding ketones by treatment with Lawesson’s reagent. The nonsymmetrical ketones were conveniently accessible via the reactions of lithiated furan, thiophene, and selenophene with N,N-dimethylbenzamide and hetarylcarboxamides, respectively, whereas the symmetrical ketones were obtained by treatment of ethyl N,N-dimethylcarbamate with 2 equiv of lithiated heterocycles. Under typical conditions, selected examples of the hetaryl thioketones were oxidized selectively to give thiocarbonyl S-oxides (sulfines). Reactions with diazomethane at –65°C yielded 1,3-dithiolanes in a regioselective manner and hetero-Diels–Alder reactions of 2-thienyl substituted thioketones with dimethyl acetylenedicarboxylate yielded the corresponding 7H-thieno[2,3- c]thiopyran-4,5-dicarboxylates.

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Item Type:Journal Article, not refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Language:English
Date:November 2014
Deposited On:10 Jun 2014 12:28
Last Modified:05 Apr 2016 17:54
Publisher:Wiley-Blackwell
ISSN:1042-7163
Funders:National Science Center (Cracow, Poland)
Additional Information:This is the accepted version of the following article: Mloston, Grzegorz; Urbaniak, Katarzyna; Gebicki, Krzystof; Grzelak, Paulina; Heimgartner, Heinz (2014). Hetaryl Thioketones: Synthesis and Selected Reactions. Heteroatom Chemistry:Epub ahead of print., which has been published in final form at http://onlinelibrary.wiley.com/doi/10.1002/hc.21191/abstract
Publisher DOI:https://doi.org/10.1002/hc.21191

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