- 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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- Copper-catalyzed cross-coupling reaction of α-sulfur-substituted alkylstannanes with acid chlorides
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Copper compounds were found to catalyze the cross-coupling reaction of α-sulfur-substituted alkylstannanes with acid chlorides. Under the optimized conditions (CuF2 (1 mol %), 1,4-dioxane, 102 C), various substrates coupled to afford the corres
- Kagoshima, Hirotaka,Takahashi, Naoshi
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p. 4558 - 4560
(2013/08/23)
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- A convenient, catalyst-free cross-coupling reaction of α-sulfur- substituted alkylstannanes with acid chlorides leading to α-sulfur- substituted ketones
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A thermal cross-coupling reaction of α-sulfur-substituted alkylstannanes with acid chlorides is described. A range of substrates can be used for the present reaction and the reaction proceeds by just mixing two components under reflux in mesitylene to giv
- Kagoshima, Hirotaka,Takahashi, Naoshi
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- A Convenient Synthesis of Thioacetates and Thiobenzoates Using Silica-Gel Supported Potassium Thioacetate
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A simple and efficient procedure has been developed for the synthesis of thioesters by a reaction of alkyl halides with silica-gel supported potassium thioacetate or thiobenzoate under mild conditions.
- Aoyama, Tadashi,Takido, Toshio,Kodomari, Mitsuo
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p. 3817 - 3824
(2007/10/03)
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- Preparation and reactivity of polyfunctional zinc and copper organometallics bearing sulfur functionalities
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Iodomethylthiobenzoate 5 and α-chloroalkyl phenyl sulfides 6 were found to insert zinc dust in THF under very mild conditions (10-25°C, 0.5-2 h) leading to zinc α-thioorganometallics. After a transmetallation with CuCN·2 LiCl, the corresponding copper rea
- Achyutha Rao,Chou, Tso-Sheng,Schipor, Ioana,Knochel, Paul
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p. 2025 - 2043
(2007/10/02)
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- A NEW METHOD FOR THE EVALUATION OF THE RELATIVE STABILITY OF ORGANOSULFUR RADICALS BY COMPETITIVE ELIMINATION TECHNIQUE
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The relative stability of various organosulfur radicals is estimated by competitive elimination technique using tributyltin radical and acetophenone derivatives having two different sulfur substituents at α and α positions.
- Ueno, Yoshio,Miyano, Tadaaki,Okawara, Makoto
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p. 443 - 446
(2007/10/02)
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