- A one step synthesis of thiazolines from esters
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Condensation of the triisobutylaluminum complex of cysteamine HCl with a variety of carboxylic esters furnishes thiazolines in one step. This new method has been applied to chiral α-aminoesters to give α-amino thiazolines of high optical purity, yet N-ben
- Busacca, Carl A.,Dong, Yong,Spinelli, Earl M.
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- Microwave-Assisted Synthesis of 2-Substituted 2-Thiazolines and 5,6-Dihydro-4 H -1,3-thiazines
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An efficient and general method for the synthesis of 2-substituted thiazolines and 5,6-dihydro-4 H -1,3-thiazines is developed via microwave-assisted ring closure of ω-thioamidoalcohols promoted by ethyl polyphosphate (PPE). The cyclization reaction involves an S N 2-type mechanism and features the advantages of very short reaction times, high yields and a predictable stereochemical outcome. The acyclic precursors are prepared in high overall yields by an improved diacylation-thionation-saponification sequence from commercially available ω-amino alcohols. The whole process is metal-free and operationally simple.
- Bisceglia, Juan A.,Kilimciler, Natalia B.,Mancinelli, Michele,Mollo, María C.,Orelli, Liliana R.
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p. 1666 - 1679
(2020/06/01)
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- Additive-free pd-catalyzed α-allylation of imine-containing heterocycles
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An additive-free Pd-catalyzed α-allylation of different imino-group-ontaining heterocycles is reported. The activation of α-CH pronucleophiles (pKa (DMSO) > 25) occurs without the addition of strong bases or Lewis acids using only the Pd/Xantphos catalyst system. The reaction scope has been studied for various 5- and 6-membered nitrogen-containing heterocycles (yields up to 96%). Mechanistic investigations suggest an initial allylation of the imine-N followed by a Pd-catalyzed formal aza-Claisen rearrangement.
- Kljajic, Marko,Puschnig, Johannes G.,Weber, Hansj?rg,Breinbauer, Rolf
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supporting information
p. 126 - 129
(2017/11/27)
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- A straightforward metal-free synthesis of 2-substituted thiazolines in air
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A base-catalysed procedure for the synthesis of 2-substituted thiazolines from nitriles and cysteamine hydrochloride under solvent-free conditions is presented. This straightforward approach allows high conversion for a broad range of nitriles and an easy
- Trose, Michael,Lazreg, Fa?ma,Lesieur, Mathieu,Cazin, Catherine S. J.
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supporting information
p. 3090 - 3092
(2015/05/27)
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- DDQ-induced dehydrogenation of heterocycles for c-c double bond formation: Synthesis of 2-thiazoles and 2-oxazoles
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Strong as an Ox: 2-Thiazoles and 2-oxazoles are formed by oxidation of 2-thiazolines and 2-oxazolines without requiring substituents at the C4 and C5 positions. DDQ plays an important role as the oxidant in this transformation and metal is unnecessary. This general procedure shows good functional group tolerance and provides a wide variety of 2-thiazoles and 2-oxazoles in moderate to excellent yields.
- Li, Xiangnan,Li, Cheng,Yin, Bing,Li, Cong,Liu, Ping,Li, Jianli,Shi, Zhen
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supporting information
p. 1408 - 1411
(2013/07/26)
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- Solvent-free tandem synthesis of 2-thiazolines and 2-oxazolines catalyzed by a copper catalyst
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Tandem reactions of nitriles with 2-aminoethanethiol hydrochloride or amino alcohols in the presence of a catalytic amount of cupric methacrylate (Cu II2L4, L = methacrylate) were employed to prepare 2-thiazolines and 2-ox
- Li, Xiangnan,Zhou, Baoyue,Zhang, Jin,She, Mengyao,An, Shujuan,Ge, Haixia,Li, Cong,Yin, Bing,Li, Jianli,Shi, Zhen
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experimental part
p. 1626 - 1632
(2012/05/04)
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- CuCl-catalyzed radical cyclisation of N-α-perchloroacyl-ketene-N,S- acetals: A new way to prepare disubstituted maleic anhydrides
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The copper-catalyzed radical cyclization (RC) of N-α-perchloroacyl cyclic ketene-N,X(X=O, NR, S)-acetals was studied. While the RC of N-acyl ketene-N,O-acetals was unsuccessful, the 5-endo cyclization of the other ketene acetals provided much better results, with the following order of cyclization efficiency: hexa-atomic cyclic ketene-N,NR-acetalspenta-atomic cyclic ketene-N,S-acetalshexa-atomic cyclic ketene-N,S-acetals. Invariably the catalytic cycle begins with the formation of a carbamoyl methyl radical. This leads to a cascade of reactions, including a radical polar crossover step, which ends with the formation of the maleimide nucleus, or precursors of this. Products from the RC of the hexa-atomic cyclic ketene-N,S-acetals, were efficiently transformed into disubstituted maleic anhydrides.
- Cornia, Andrea,Felluga, Fulvia,Frenna, Vincenzo,Ghelfi, Franco,Parsons, Andrew F.,Pattarozzi, Mariella,Roncaglia, Fabrizio,Spinelli, Domenico
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experimental part
p. 5863 - 5881
(2012/09/22)
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- A simple O-sulfated thiohydroximate molecule to be the first micromolar range myrosinase inhibitor
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New non-hydrolyzable analogues of glucosinolates have been prepared. Myrosinase inhibition was observed with modified aglycon moieties, even bulky phenothiazine analogue 6 gave reasonable inhibition. The simplest structure 8 derived from dimethylaminoethanethiol has shown to be the most potent inhibitor with an IC50 of 3.32 μM.
- Cerniauskaite, Deimante,Gallienne, Estelle,Karciauskaite, Henreta,Farinha, Andrea S.F.,Rousseau, Jolanta,Armand, Sylvie,Tatibou?t, Arnaud,Sackus, Algirdas,Rollin, Patrick
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scheme or table
p. 3302 - 3305
(2009/08/09)
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- Straightforward microwave-assisted synthesis of 2-thiazolines using Lawesson's reagent under solvent-free conditions
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2-Thiazolines are synthesized from carboxylic acids and 1,2-aminoalcohols in the presence of Lawesson's reagent under solventless conditions. The developed method is valid for either substituted or unsubstituted aminoalcohols and a wide variety of aromatic, heteroaromatic and aliphatic carboxylic acids; thus it constitutes a general synthetic method for these kinds of compounds. The role of Lawesson's reagent is dual: to transform the 1,2-aminoalcohol into 1,2-aminothiol and to activate its reaction with the carboxylic acid leading to the formation of a thiazoline ring, all in one pot.
- Seijas, Julio A.,Vázquez-Tato, M. Pilar,Crecente-Campo, José
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p. 9280 - 9285
(2008/12/21)
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- Thionation of N-(ω-halogenoalkyl)-substituted amides with Lawesson's reagent: Facile synthesis of 4,5-dihydro-1,3-thiazoles and 5,6-dihydro-4H-1,3- thiazines
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The thionation and cyclization of N-(ω-halogenoalkyl)-substituted amides (and related compounds) with Lawesson's reagent (LR = 2,4-bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane 2,4-disulfide) has been investigated. Treatment of the amides 1 with LR gav
- Kodama, Yasuhiro,Ori, Mayuko,Nishio, Takehiko
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p. 187 - 193
(2007/10/03)
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- Palladium-catalyzed cross-coupling of benzylzinc reagents with methylthio N-heterocycles: A new coupling reaction with unusual selectivity
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Benzylzinc reagents undergo palladium-catalyzed cross-coupling reactions with methylthio-substituted N-heterocycles in moderate to good yields. 2- (Methylthio)pyrimidines are particularly reactive substrates for this reaction. As a result, the regioselectivity of 2,4-bis(methylthio)pyrimidines is opposite to that of their 2,4-dichloropyrimidine analogues. This unusual cross-coupling reaction offers new flexibility in the regioselective synthesis of substituted pyrimidines and other heterocycles.
- Angiolelli, Mary E.,Casalnuovo, Albert L.,Selby, Thomas P.
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p. 905 - 907
(2007/10/03)
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- Synthese, activites anti-parasitaire et anti-fongique d'arylalkyl- et d'arylvinylthiazolines
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Synthesis, anti-parasitic and anti-fungal activities of arylalkyl and arylvinylthiazolines.Twenty-seven arylalkyl- or arylvinylthiazolines were synthesized and tested in vitro against three genera of nematodes, various yeasts and opportunistic fungi.Vinyl
- Caujolle, R,Baziard-Mouysset, G,Favrot, J D,Payard, M,Loiseau, P R,et al.
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