- Synthesis of β-oxo carbonyl and thiocarbonyl compounds via basic sulfur abstraction
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Sulfur abstraction from suitable thioesters represents a mild method for the formation of carbon-carbon bonds and the formation of 1,3-dicarbonyl compounds. A study of the scope and limitations of this reaction for the synthesis of these or mixed 1,3-carbonyl/thiocarbonyl compounds by a base promoted sulfur abstraction rearrangement is described. These reactions were typically very clean and the products were obtained in good yield (65–95%) in just 30 min. This method is particularly efficient for the introduction of thiocarbonyl containing groups. Thus, it constitutes a synthetic strategy for the generation of a new carbon-carbon bond and the regioselective preparation of mixed β-dicarbonyl compounds.
- Silva, Saúl,Maycock, Christopher D.
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- α-Methylphenacyl thioesters as convenient thioacid precursors
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α-Methylphenacyl (Mpa) thioesters are described as precursors of thioacids. Mpa thioesters are accessible via the condensation of carboxylic acids and phenacyl thiol, which is easily prepared without column chromatography. The Mpa thioesters are selectively deprotected by reduction with zinc dust in the presence of conventional thioacid protecting groups. In addition, the Mpa group exhibits orthogonal reactivity to the Boc group. These features are expected to facilitate the preparation of complex thioacids, including those in peptides.
- Hatanaka, Toru,Yuki, Ryosuke,Saito, Ryota,Sasaki, Kaname
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supporting information
p. 10589 - 10592
(2016/11/30)
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- Exploration and Optimization of an Efficient One-pot Sequential Synthesis of Di/tri-substituted Thiazoles from α-Bromoketones, Thioacids Salt, and Ammonium Acetate
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Exploration of scope of an optimized one-pot sequential procedure for preparing of 2,4-di- and 2,4,5-tri-substituted thiazoles has been accomplished. The synthesis was performed by the initial formation of a β-keto-thioester intermediate from nucleophilic substitution of α-bromoketones with thioacid potassium salts, followed by treatment with ammonium acetate and one equivalent of acetic acid in toluene to form imine intermediate eventually leading to cyclization yielding thiazoles. This procedure should be highlighted with a flexible way to control the substitution pattern around thiazole ring by choosing appropriately substituted α-bromoketones even containing acid labile functionality and thioacid potassium salts, and thus its applicability is very wide.
- Venkateswararao, Eeda,Jalani, Hitesh B.,Manoj,, Manickam,Jung, Sang-Hun
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supporting information
p. 1449 - 1456
(2016/09/24)
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- A novel method for the synthesis of thioacetates using benzyltriethyl- ammonium tetrathiomolybdate and acetic anhydride
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Herein we report a simple and efficient methodology for the synthesis of thioacetates using benzyltriethylammonium tetrathiomolybdate and acetic anhydride as the key reagents, starting from alkyl halides in a multistep, tandem reaction process. Its application in the synthesis of orthogonally protected cysteine and anomeric β-thioglycosides has also been demonstrated.
- Nasir, Baig R. B.,Sai, Sudhir V.,Srinivasan, Chandrasekaran
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experimental part
p. 2684 - 2688
(2009/04/16)
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- Synthesis of multisubstituted furans, pyrroles, and thiophenes via ynolates
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An efficient synthetic method for the preparation of multisubstituted furans, thiophenes, and pyrroles using ynolates was developed. This novel formal [4 + 1] annulation by C2-C3 and C3-C4 bond formations Includes cycloaddition, cyclization, decarboxylati
- Shindo, Mitsuru,Yoshimura, Yutaka,Hayashi, Maiko,Soejima, Hiroe,Yoshikawa, Takashi,Matsumoto, Kenji,Shishido, Kozo
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p. 1963 - 1966
(2008/02/02)
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