- Chemo- and regioselective synthesis of alkyl-3-thiazoline carboxylates
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The synthesis of a series of allyl substituted 3-thiazoline-carboxylates was carried out from the corresponding thiazolidines, by a MnO2-mediated oxidation reaction under mild conditions. The reaction was chemoselective towards the amine-imine oxidation and was also regioselective, affording the unsaturation at the 3-position of the heterocycle.
- Fernandez, Xavier,Fellous, Roland,Lizzani-Cuvelier, Louisette,Loiseau, Michel,Duach, Elisabet
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- Copper(II)-catalyzed oxidation of 4-carboxythiazolines and 4-carboxyoxazolines to 4-carboxythiazoles and 4-carboxyoxazoles
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A mild copper(II)-catalyzed oxidation of 4-carboxythiazolines and 4-carboxyoxazolines to 4-carboxythiazoles and 4-carboxyoxazoles has been developed. Various substrates with alkyl or aryl substitutions at 2-position on azoline ring could be smoothly oxidi
- Wang, Yiyun,Li, Ziyuan,Huang, Yue,Tang, Changhua,Wu, Xiaoming,Xu, Jinyi,Yao, Hequan
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supporting information; experimental part
p. 7406 - 7411
(2011/10/09)
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- Oxidation of 4-carboxylate thiazolines to 4-carboxylate thiazoles by molecular oxygen
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A facile and environment-benign oxidation by molecular oxygen was applied for the conversion of 4-carboxylate thiazolines to 4-carboxylate thiazoles. The substituent effect on thiazoline ring was investigated. It was found that electron-poor group on the thiazoline ring could facilitate the oxidation.
- Huang, Yue,Gan, Haifeng,Li, Shang,Xu, Jinyi,Wu, Xiaoming,Yao, Hequan
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supporting information; experimental part
p. 1751 - 1753
(2010/05/18)
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- Asymmetric synthesis of 2-alkyl-3-thiazoline carboxylates: Stereochemistry of the MnO2-mediated oxidation of cis- and trans-2-alkyl-thiazolidine-(4R)-carboxylates
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The asymmetric synthesis of a series of 3-thiazoline carboxylates, 2, was effected by MnO2 oxidation of the corresponding cis/trans thiazolidines, 1. The stereochemistry of the oxidation reaction was studied using NMR and chiral GC analyses. Compounds 2 were obtained with enantiomeric excesses (e.e.s) in the range of 40-100%.
- Fernandez, Xavier,Duach, Elisabet
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p. 1279 - 1286
(2007/10/03)
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- TETRACYCLIC COMPOUNDS AS DOPAMINE AGONISTS
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A tetracyclic compound of the formula: STR1 wherein A and the atoms to which it is attached and the optional double bond represent a mono-or di-heterocyclic ring selected from: STR2 wherein R 1, R. sup.2, R 3, R 4 and X are specifically defined, which compounds are useful in the treatment of dopamine-related neurological, psychological and cardiovascular disorders as well as in the treatment of substance abuse and other addictive behavior disorders, cognitive impairment and attention deficit disorder.
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- Oxidation of oxazolines and thiazolines to oxazoles and thiazoles. Application of the Kharasch-Sosnovsky reaction
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Using a modification of the Kharasch-Sosnovsky reaction, the oxidation of oxazolines and thiazolines bearing a variety of 2-alkyl substituents (chiral and achiral) were smoothly oxidized to their corresponding oxazoles and thiazoles, respectively. The key feature involved in the successful implementation of this important oxidation was the use of a mixture of Cu(I) and Cu(II) salts to enhance the oxidation of the intermediate captodative radical, 24. The main limitation of this method was shown when the oxidation failed with oxazolines/thiazolines lacking the carboalkoxy group at C-4.
- Meyers,Tavares, Francis X.
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p. 8207 - 8215
(2007/10/03)
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- The Oxidation of 2-Oxazolines to 1,3-Oxazoles
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Oxazolines are readily oxidized to 1,3-oxazoles using NBS/peroxide or light or, more efficiently, by the Kharasch-Sosnovsky Reaction.
- Meyers, A. I.,Tavares, Francis
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p. 2481 - 2484
(2007/10/02)
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