- Organocatalytic and enantioselective [4+2] cyclization between hydroxymaleimides and: Ortho -hydroxyphenyl para -quinone methide-selective preparation of chiral hemiketals
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A cinchona alkaloid squaramide promoted enantioselective [4+2] cyclization between hydroxymaleimides and ortho-hydroxyphenyl p-QMs has been disclosed, and a wide range of chiral hemiketals containing chromane and succinimide frameworks with two adjacent quaternary stereogenic centers have been prepared for the first time with excellent results (up to 99% yield, up to 99?:?1 dr, up to >99% ee) under mild conditions. This journal is
- Xiang, Min,Li, Chen-Yi,Song, Xiang-Jia,Zou, Ying,Huang, Zhi-Cheng,Li, Xia,Tian, Fang,Wang, Li-Xin
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supporting information
p. 14825 - 14828
(2020/12/07)
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- Organocatalytic Asymmetric Annulation between Hydroxymaleimides and Nitrosoarenes: Stereoselective Preparation of Chiral Quaternary N-Hydroxyindolines
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An unusual and highly effective asymmetric annulation of nitrosoarenes with hydroxymaleimides catalyzed by a chiral bifunctional amine squaramide catalyst has been disclosed. A wide range of highly fused chiral N-hydroxyindolines with two consecutive quaternary stereocenters and multifunctional groups were directly and effectively prepared in excellent yields (up to >99%) with complete regioselective cyclization and excellent stereoselectivities (up to >99:1 dr and >99% ee). The efficiency and potentials of the new reaction and the target chiral entities were well demonstrated by delicate transformations into a series of new chiral indolines.
- Yang, Yu,Ren, Hong-Xia,Chen, Feng,Zhang, Zheng-Bing,Zou, Ying,Chen, Chao,Song, Xiang-Jia,Tian, Fang,Peng, Lin,Wang, Li-Xin
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supporting information
p. 2805 - 2808
(2017/06/07)
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- Rapid Vortex Fluidics: Continuous Flow Synthesis of Amides and Local Anesthetic Lidocaine
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Thin film flow chemistry using a vortex fluidic device (VFD) is effective in the scalable acylation of amines under shear, with the yields of the amides dramatically enhanced relative to traditional batch techniques. The optimized monophasic flow conditions are effective in ≤80seconds at room temperature, enabling access to structurally diverse amides, functionalized amino acids and substituted ureas on multigram scales. Amide synthesis under flow was also extended to a total synthesis of local anesthetic lidocaine, with sequential reactions carried out in two serially linked VFD units. The synthesis could also be executed in a single VFD, in which the tandem reactions involve reagent delivery at different positions along the rapidly rotating tube with in situ solvent replacement, as a molecular assembly line process. This further highlights the versatility of the VFD in organic synthesis, as does the finding of a remarkably efficient debenzylation of p-methoxybenzyl amines.
- Britton, Joshua,Chalker, Justin M.,Raston, Colin L.
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supporting information
p. 10660 - 10665
(2015/07/20)
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- Preparation of amides mediated by isopropylmagnesium chloride under continuous flow conditions
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A safe, green and functional-group-tolerant flow version of the direct amide bond formation mediated by Grignard reagents (the Bodroux reaction) is described. The procedure can be applied to a wide variety of primary and secondary amines and anilines, as well as to aromatic and aliphatic esters. The flow approach leads to improved yields and selectivities in the reaction, which has a sustainable purification procedure and a simple scale-up. This reaction represents an efficient and green alternative to the use of alkylaluminium and metal-catalyzed procedures.
- Munoz, Juan De M.,Alcazar, Jesus,De La Hoz, Antonio,Diaz-Ortiz, Angel,Alonso De Diego, Sergio-A.
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supporting information; experimental part
p. 1335 - 1341
(2012/06/04)
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- Synthesis, structure-activity relationship, and receptor pharmacology of a new series of quinoline derivatives acting as selective, noncompetitive mGlu1 antagonists
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We describe the discovery and the structure-activity relationship of a new series of quinoline derivatives acting as selective and highly potent noncompetitive mGlu1 antagonists. We first identified cis-10 as a fairly potent mGlu1 antagonist (IC50/s
- Mabire, Dominique,Coupa, Sophie,Adelinet, Christophe,Poncelet, Alain,Simonnet, Yvan,Venet, Marc,Wouters, Ria,Lesage, Anne S. J.,Van Beijsterveldt, Ludy,Bischoff, Fran?ois
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p. 2134 - 2153
(2007/10/03)
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- SUBSTITUTED ANILINE DERIVATIVES
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The present invention relates to aniline derivatives of the general formula I or pharmaceutically acceptable salts thereof and their use.
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- Photochemical Bromination of Anilides by Benzenehexabromide
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Benzenehexabromide was found to afford photochemical bromination of substituted acetanilide in the p-position.The rates of bromination were found to follow the order predicted on the basis of inductive effect of the substituents and similar to the sequence of reactivities observed for bromination of acetanilides with N-bromosuccinimide.Similar results were obtained in the case of p-substituted benzanilides and the reaction shows a good Hammett correlation with the ?+ values for the substituents with a ρ value -0.266.
- Aly, M. M.,Awad, I. M. A.,Fahmy, A. M.
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