84272-19-5Relevant academic research and scientific papers
Selective: S -arylation of 2-oxazolidinethiones and selective N -arylation of 2-benzoxazolinones/2-benzimidazolinones
Sun, Chu-Han,Lu, Yi,Zhang, Qing,Lu, Rong,Bao, Lin-Qing,Shen, Mei-Hua,Xu, Hua-Dong
supporting information, p. 4058 - 4063 (2017/07/10)
There exist three possible patterns for the reaction of cyclic 2-oxazolidinethione and 2-benzoxazolidinethione with arynes, namely (a) S-arylation, (b) N-arylation, and (c) aryne insertion into the thiocarbonyl group (CS). Our studies demonstrate that S-arylation wins out affording S-aryl dihydrooxazoles. In contrast, for related reactions of cyclic 2-benzoxazolinone and 2-benzimidazolinone with arynes, it is found that N-arylation outcompetes O-arylation and aryne insertion into the CO group to give N-aryl 2-benzoxazolinones and N-aryl 2-benzimidazolinones.
Convenient approach to chiral 4-monosubstituted 1,3-oxazolidine-2-thiones
Lu, Zheng,Yang, Yong-Qing,Li, Jiu-Hui,Wei, Jun-Nan,Wang, Yi-Zhu
supporting information, p. 2215 - 2219 (2017/10/31)
Chiral 4-monosubstituted 1,3-oxazolidine-2-thiones are regarded as one of the modified version of Evans auxiliaries in asymmetric aldol condensation, which can generate two adjacent chiral carbon centers in one time They have advantages over Evans auxiliaries in some aspects, however, their application is highly limited by their preparation approaches as toxic or flammable chemicals are involved. Here, a mild and applicable procedure for preparing the chiral oxazolidine-2-thione auxiliaries has been developed in this article. Potassium ethylxanthate and the corresponding chiral amino alcohols as the starting material in absolute ethanol are mixed and the mixture are heated under reflux for 1 h in open air to provide 1,3-oxazolidine-2-thiones chiral auxiliaries in moderate to excellent yields.
Thiocarbonyl Surrogate via Combination of Sulfur and Chloroform for Thiocarbamide and Oxazolidinethione Construction
Tan, Wei,Wei, Jianpeng,Jiang, Xuefeng
supporting information, p. 2166 - 2169 (2017/04/27)
An efficient and practical thiocarbonyl surrogate via combination of sulfur and chloroform has been developed. A variety of thiocarbamides and oxazolidinethiones have been established, including chiral thiourea catalysts and chiral oxazolidinethione auxiliaries with high selectivity. Meanwhile, pesticides Diafenthiuron (an acaricide), ANTU (a rodenticide), and Chloromethiuron (an insecticide) were practically synthesized through this method in gram scale. Dicholorocarbene, as the key intermediate, was further confirmed via a carbene-trapping control experiment.
Synthesis, X-ray analysis, and biological activities of novel oxazolidinethiones
Saygili, Nezire,?zalp, Meral,Yildirim, Leyla Tatar
, p. 1264 - 1269 (2015/04/27)
Oxazolidinethione compounds were synthesized starting from racemic and enantiopure β-amino alcohols. The molecular structure of oxazolidinethione 6a was elucidated by single-crystal x-ray crystallography. Oxazolidinethione compounds screened for antimicro
N-(diazoacetyl)oxazolidin-2-thiones as sulfur-donor reagents: Asymmetric synthesis of thiiranes from aldehydes
Cano, Israel,G?mez-Bengoa, Enrique,Landa, Aitor,Maestro, Miguel,Mielgo, Antonia,Olaizola, Iurre,Oiarbide, Mikel,Palomo, Claudio
supporting information, p. 10856 - 10860 (2013/01/15)
Sulfur tyranny: Thiiranes, instead of oxiranes, can be obtained in a highly stereoselective manner through the cycloaddition reaction of N-acyl oxazolidine tethered diazo thione compounds with aldehydes catalyzed by RhII. Thus, this reaction provides versatile adducts S functionalized at both the α and β position, with concomitant generation of two contiguous stereocenters. Copyright
On the influence of chiral auxiliaries in the stereoselective cross-coupling reactions of titanium enolates and acetals
Baiget, Jessica,Cosp, Annabel,Gálvez, Erik,Gómez-Pinal, Loreto,Romea, Pedro,Urpí, Fèlix
, p. 5637 - 5644 (2008/09/21)
Titanium enolates from chiral N-propanoyl-1,3-thiazolidine-2-thiones containing bulky substituents at C4 turned out to be excellent platforms to get highly stereocontrolled cross-coupling reactions with acetals. Related oxazolidinethiones also afforded go
Intramolecular sulfur transfer in N-enoyl oxazolidine-2-thiones promoted by Bronsted acids. Practical asymmetric synthesis of β-mercapto carboxylic acids and mechanistic insights
Palomo, Claudio,Oiarbide, Mikel,Lopez, Rosa,Gonzalez, Pedro B.,Gomez-Bengoa, Enrique,Saa, Jose M.,Linden, Anthony
, p. 15236 - 15247 (2007/10/03)
The ability of Bronsted acids alone to efficiently promote the sulfur transfer process in N-enoyl oxazolidine-2-thiones to give β-mercapto carbonyl derivatives is demonstrated. The reactions proceed with essentially perfect diastereocontrol for a range of alkyl-substituted N-enoyl oxazolidine-2-thiones (d.r. regularly above 98:2) and high selectivity for most aryl-substituted counterparts (d.r. typically above 92:8). Importantly, the reaction works remarkably well in β,β-disubstituted N-enoyl oxazolidine-2-thiones as well, giving rise to quaternary C-S stereocenters in selectivities usually above 95:5. The relative efficiency of a range of acids (trifluoroacetic, difluoroacetic, acetic, triflic) is assessed showing TFA and TfOH as the most efficient and acetic acid as a totally inefficient reaction promoter. The new procedure complements the Lewis acid promoted reaction previously described by our group in two aspects: First, stereodivergent results are obtained for the Lewis acid or Bronsted acid promoted reactions of β,β-disubstituted enoyl compounds. Second, while the Bronsted acid promoted reactions are stereospecific, providing a good correlation between the substrate E/Z configuration and products stereochemistry, the reactions mediated by Lewis acids (BF3/OEt2) provide invariant d.r. values regardless of the E/Z composition of the starting olefin. The synthetic value of the method is illustrated by (a) removal of the oxazolidinone moiety from the rearranged products under reducing conditions (NaBH4, H 2O-THF) which yields β-mercapto alcohols and (b) treatment with Sm(OTf)3 in MeOH which affords the corresponding β-mercapto carboxylic esters, both categories of compounds being isolated in up to 97% ee. Remarkably, the method constitutes the first general approach to highly enantioenriched building blocks bearing a quaternary C-S stereocenter. On the other hand, spectroscopic and inhibition experiments are carried out that demonstrate the participation of protons also in the Lewis acid promoted reactions. Finally, the computational studies carried out at the B3LYP/6-31G* level give support for an activation of the substrate enoyl by complexation with two molecules of either the Bronsted or Lewis acid and serve to explain the stereochemical outcome of the reactions.
A facile access to chiral 4-isopropyl-, 4-benzyl-, and 4-phenyloxazolidine-2-thione
Wu, Yikang,Yang, Yong-Qing,Hu, Qi
, p. 3990 - 3992 (2007/10/03)
A highly practical procedure for preparing the chiral oxazolidine-2-thione auxiliaries using carbon disulfide and the corresponding chiral amino alcohols as the starting materials in the presence of potassium carbonate and hydrogen peroxide is presented.
Construction of C-S bonds with a quaternary stereocenter through a formal Michael reaction: Asymmetric synthesis of tertiary thiols
Palomo, Claudio,Oiarbide, Mikel,Dias, Flavia,Lopez, Rosa,Linden, Anthony
, p. 3307 - 3310 (2007/10/03)
Quaternary stereocenters that bear a sulfur substituent can be created with nearly perfect stereocontrol through an intramolecular Michael-type process. Lewis acids (L.A.) accelerate the intramolecular sulfur-atom transfer from the oxazolidine-2-thione functionality to the β carbon atom of the β,β-disubstituted enoyl moiety, whereas the chirality of the oxazolidine-2-thione portion controls reaction stereochemistry (see scheme).
MUSCARINIC AGONISTS
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Page 23, (2010/02/09)
The present invention relates to compounds of Formula (I): which are agonists of the M-1 muscarinic receptor.
