- Straightforward Synthesis of 1,2,3-Tricarbonyl Systems
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A simple two-step protocol for the preparation of α,β-diketo amides is described.The first step involves condensation of the anion of an α-phenylthio amide with an aldehyde.This is followed by oxidation of the resulting β-hydroxy α-sulfide with the Dess-Martin periodinane.The vicinal tricarbonyl system is obtained in good to excellent yields.
- Linde, Robert G.,Jeroncic, Lucio O.,Danishefsky, Samuel J.
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p. 2534 - 2538
(2007/10/02)
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- Further Reactions in the Tetrahydroazocin-2(1H)-one Series
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5,6,7,8-Tetrahydroazocin-2(1H)-one and the 3-phenylthio- and 3-phenylthiosulfonyl-substituted derivatives have been converted into the corresponding 2-ethoxy-5,6,7,8-tetrahydroazocines with Meerwin's reagent.Upon irradiation under mercury lamp at longer w
- Ridley, Damon D.,Simpson, Gregory W.
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p. 687 - 698
(2007/10/02)
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- New Unusually Photochemical Reactions of 3-Aminosydnones
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The light-induced reactions of the 3-amino-4-(phenylthio)sydnones 1a - d surprisingly produce beside diphenyl disulfide the sydnone isomers 11a - d with 2-aza-1,3-diazoniacyclopentadiene-1,4-diolate structure in 2,3 - 27percent yields.The photoreactions of the sydnones 1a, c in the presence of dimethyl acetylenedicarboxylate proceed with formation of the photoisomers 11a or 11c (17percent), the benzothiophene derivative 14 (9 - 7percent), the (phenylthio)fumaric ester 15 (5percent) as well as the pyrazole derivatives 13a (18percent) or 13c (8percent), respectively.The latter are results of a thermal cycloaddition reaction of the photochemically generated nitrile imine intermediate of type 9 to dimethyl acetylenedicarboxylate.Beside 14 (30 - 43percent), the same pyrazole derivatives 13a, c are obtained on irradiation of the sydnone isomers 11a or 11c in the presence of dimethyl acetylenedicarboxylate, respectively.The analogous photoreaction of the system 1d/dimethyl acetylenedicarboxylate produces 11d (0.6percent) and 13d (1.8percent) in low yields.
- Gotthardt, Hans,Reiter, Friedemann
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p. 1737 - 1745
(2007/10/02)
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