- Syntheses of 4H-thiopyran-4-one 1,1-dioxides as precursors to sulfone-containing analogues of tetracyanoquinodimethane
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Synthetic routes to the unsubstituted 4H-thiopynan-4-one 1,1-dioxide (5a), 2,6-dialkyl-substituted, 2-aryl- or 2-heteroaryl-6-alkyl-substituted, 2,6-diaryl- or diheteroaryl-substituted, and 2-heteroaryl-6-aryl-substituted 4H-thiopyran-4-one 1,1-dioxides 5b-s are described. Sodium hydrosulfide hydrate in buffered aqueous alcohol can be used as a substitute for hydrogen sulfide gas for the introduction of sulfur to methyl acrylate, to 1,5-disubstituted-1,4-pentadien-3-ones 13, or to 1,5-disubstituted-1,4-pentadiyn-3-ones 17. The double dehydrogenation of 2,3,5,6-tetrahydrothiopyran-4-one 1,1-dioxides 13 with iodine-DMSO-sulfuric acid gives thiopyran-4-one 1,1-dioxides 5 in good yield and small amounts of 1,4-pentadien-3-ones 13. 2,3,5,6-Tetrahydrothiopyran-4-one 1,1-dioxide (9) and 5,6-dihydrothiopyran-4-one 1,1-dioxide (12), which lack aryl or heteroaryl substituents, give poor yields of 4H-thiopyran-4-one 1,1-dioxide (5a) with iodine-DMSO-sulfuric acid.
- Rule,Detty,Kaeding,Sinicropi
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p. 1665 - 1673
(2007/10/02)
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- A NEW SYNTHESIS OF 4H-THIOPYRAN-4-THIONES FROM ACETYLENIC β-DIKETONES
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2,6-Diaryl-4H-thiopyran-4-thiones have been synthesized in excellent yields by the reaction of 1-aryl-5-phenyl-4-pentyne-1,3-diones with phosphorus pentasulfide in dry pyridine at room temperature and were converted into the corresponding hydrazones and o
- Marei, Mohamed Gaber
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p. 101 - 110
(2007/10/02)
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- Chemistry of 1,1-Dioxothiopyrans. 1. Syntheses and Reactions of 2,6-Diphenyl-4H-thiopyran-4-one 1,1-Dioxide and 4H-Thioflaven-4-one, 1,1-Dioxide
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Improved syntheses and certain reactions of 2,6-diphenyl-4H-thiopyran-4-one 1,1-dioxide and 4H-thioflaven-4-one 1,1-dioxide are reported.Many of these derivatives, which display reversible, one-electron reduction waves in their cyclic voltammograms betwee
- Chen, Chin H.,Reynolds, George A.,Luss, H. R.,Perlstein, Jerome H.
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p. 3282 - 3289
(2007/10/02)
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- THE OXIDATION REACTIONS OF THIOPYRANS
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A method was developed for the preparation of compounds with 4H-thiopyrone structure by the oxidation of the corresponding 4H-thiopyranes and their condensed analogs by potassium permanganate.
- Plotnikov, A. M.,Shebaldova, A. D.,Kharchenko, V. G.
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p. 1226 - 1229
(2007/10/02)
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