2519-89-3Relevant articles and documents
Method for preparing 2,4-disubstituted thiazoline compound from acyl chloride
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Paragraph 0052; 0053; 0054; 0055; 0056, (2017/05/23)
The invention provides a novel method for preparing 2,4-disubstituted thiazoline at high yield by firstly reacting acyl chloride serving as a raw material and beta-azide disulfide and also provides a general formula I and application of a product, namely a 2,4-disubstituted thiazoline compound. By using the method, the defects of synthesis complexity, high byproduct yield and slightly low yield of the existing method are overcome, and the method has the advantages of high yield (up to 90% or above), high repeatability and suitability for preparation on a relatively large scale.
Cu(i)-Catalyzed oxidative homo-coupling of thiazoline-4-carboxylates: Synthesis of 4,4′-bithiazoline derivatives
Fang, Xinxin,Zhang, Kaifan,Yao, Hequan,Huang, Yue
supporting information, p. 8030 - 8034 (2016/09/09)
Cu(i)-Catalyzed oxidative homo-coupling of thiazoline-4-carboxylates with good functional group tolerance has been developed. The methodology presented an efficient method to directly construct vicinal carbon-hetero quaternary centers existing in numerous functional molecules and could be applied to the synthesis of 4,4′-bithiazoles which are difficult to prepare by direct C-H activation.
Concise synthesis of 2,4-disubstituted thiazoles from β-azido disulfides and carboxylic acids or anhydrides: Asymmetric synthesis of cystothiazole C
Liu, Yi,Sun, Xue,Zhang, Xing,Liu, Jun,Du, Yuguo
, p. 8453 - 8461 (2014/12/10)
A novel and efficient method for the one-pot synthesis of 2,4-disubstituted thiazoles from carboxylic acids or anhydrides is presented. Based on this new method, the total synthesis of the bis-2,4-disubstituted bis(thiazoles) natural product cystothiazole C is also presented. This journal is
One-pot synthesis of 2,4-disubstituted thiazoline from β-azido disulfide and carboxylic acid
Liu, Yi,Liu, Jun,Qi, Xiangbing,Du, Yuguo
experimental part, p. 7108 - 7113 (2012/10/07)
A concise and efficient one-pot four-step synthesis of 2,4-disubstituted thiazoline via a cascade disulfide bond cleavage/thiocarbonylation/Staudinger reduction/aza-Wittig reaction is established. Treatment of various carboxylic acids with β-azido disulfides under this one-pot procedure obtained the desired thiazolines in good to excellent isolated yields.
Copper-catalyzed oxidation of azolines to azoles
Dawsey, Anna C.,Li, Vincent,Hamilton, Kimberly C.,Wang, Jianmei,Williams, Travis J.
experimental part, p. 7994 - 8002 (2012/08/08)
We report herein convenient, aerobic conditions for the oxidation of thiazolines to thiazoles and data regarding the oxidation mechanism. These reactions feature operationally simple and environmentally benign conditions and proceed in good yield to afford the corresponding azoles, thus enabling the inexpensive preparation of valuable molecular building blocks. Incorporation of a novel diimine-ligated copper catalyst, [(MesDABMe) CuII(OH2)3]2+ [-OTf] 2, provides increased reaction efficiency in many cases. In other cases copper-free conditions involving a stoichiometric quantity of base affords superior results.
Efficient synthesis of primary 2-aminothiols from 2-aminoalcohols and methyldithioacetate
Mercey, Guillaume,Brégeon, Delphine,Gaumont, Annie-Claude,Levillain, Jocelyne,Gulea, Mihaela
scheme or table, p. 6553 - 6555 (2009/04/05)
Various primary 2-aminothiols have been prepared by a general and efficient method, in three steps, starting from commercially available 2-aminoalcohols and methyldithioacetate as a convenient source of sulfur.
An enantioselective ketene-imine cycloaddition method for synthesis of substituted ring-fused 2-pyridinones
Emtenaes,Alderin,Almqvist
, p. 6756 - 6761 (2007/10/03)
Previously, a method for the stereoselective synthesis of β-lactams, starting from 2H-δ2-thiazolines and Meldrum's acid derivatives, has been reported from our laboratory. We now report a new method for the synthesis of optically active, highly substituted ring-fused 2-pyridinones. This was discovered when 2-alkyl-δ2-thiazolines and Meldrum's acid derivatives were treated with HCl(g) in benzene at 5 → 78 °C. Further refinement of the synthetic protocol revealed that use of 1,2-dichloroethane as solvent at 0 → 64 °C led to the desired 2-pyridinones in good yields and with excellent enantioselectivity. Use of these conditions allowed preparation of 2-pyridinones from several different δ2-thiazolines and Meldrum's acid derivatives and may be a general route to 2-pyridinones.
Amino Acids, 12. - Syntheses of DL-Cysteines from Acrylic Acid Derivatives
Effenberger, Franz,Beisswenger, Thomas,Dannenhauer, Fritz
, p. 2209 - 2224 (2007/10/02)
The addition of sulfenyl chlorides 1 to 2-alkenoic acid esters 2 gives mixtures of 2(3)-chloro-3(2)-thioalkenoic acid esters 3/4, whereas the addition of thiols 7 to methyl 2-chloro-2-propenoate (6) results in the formation of methyl 2-chloro-3-thiopropanoates 3 only.The dependence of the isomerization of 3 to 4 on the reaction conditions was investigated; at higher temperatures the formation of 4 is especially favored.At temperatures below 55 deg C the 2-azido compounds 8 are obtained without isomerization from 3 by reaction with sodium azide in the presence of a PT catalyst.Cysteine derivatives 9 or 10, resp., are obtained by hydrogenation of 8 with H2S/pyridine/H2O or with H2/Re2S; the overall yields of 9 or 10, resp., starting from 6 are as high as 70percent.DL-Cysteine is obtained in good overall yields as hydrochloride hydrate 16 by HCl-catalyzed hydrolysis of the 2-thiazolines 15a*HCl and 15e, which are prepared by HCl-catalyzed addition of thioacetamide (11a) to α-chloroacrylic acid (12) or the amide 13 and consecutive ring closure.
Synthesis and Nuclear Magnetic Resonance Study of 2-Thiazolines
Eggleton, Gordon L.,Bushman, Daniel R.,Whitlock, David W.,Pugh, Darrell K.,Chance, Katherine L.
, p. 351 - 354 (2007/10/02)
A series of 5,5-dimethyl-2-thiazoline-4-carboxylates with a phenyl or methyl group at the 2-position of the ring were prepared from the corresponding methyl or ethyl ester of penicillamine and either methyl benzimidate or ethyl acetimidate.The free acid was obtained by the reaction of penicillamine with benzonitrile to produce 5,5-dimethyl-2-phenyl-2-thiazoline-4-carboxylic acid.Corresponding thiazolines were prepared from cysteine in the same manner.The nuclear magnetic resonance spectra of both series exhibit coupling of the methyl group at the 2-position with the hydrogen at the 4-position.The groups at the 5-position are nonequivalent and in the case of the cysteine series give rise to an ABX system.Further analysis confirms a concentration dependence for this splitting pattern.
