- Application of primary halogenated hydrocarbons for the synthesis of 3-Aryl and 3-Alkyl indolizines
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Indolizine is an important heterocyclic compound with several interesting properties that make it suitable for numerous applications in many fields, such as biology, medicine and materials. However, the synthesis of 3-Alkyl indolizines from bulky primary halogenated alkanes has not yet been reported. Herein, a transition-metal-free synthetic route to 3-Aryl and 3-Alkyl indolizines from electron-deficient alkenes, pyridines and primary halogenated hydrocarbons has been reported for the first time using a tandem reaction. The key step of this method is the oxidative dehydrogenative aromatization of a tetrahydroindolizine intermediate with 2,2,6,6-Tetramethylpiperidine-N-oxyl (TEMPO) as the oxidant. The advantages of this protocol are its use of easily available and low-cost starting materials, the transition-metal-free conditions and its ready scalability.
- Liu, Yan,Hu, Huayou,Zhou, Junyu,Wang, Wenhui,He, Youliang,Wang, Chao
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p. 5016 - 5024
(2017/07/10)
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- Transition-Metal-Free Synthesis of Indolizines from Electron-Deficient Alkenes via One-Pot Reaction Using TEMPO as an Oxidant
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A one-pot method for the synthesis of multisubstituted indolizines from α-halo carbonyl compounds, pyridines, and electron-deficient alkenes is reported. The oxidative dehydrogenation reaction takes place under transition-metal-free conditions using TEMPO as an oxidant. This protocol uses ready available starting materials in a convenient procedure under mild reaction conditions.
- Shi, Fei,Zhang, Yu,Lu, Zhaole,Zhu, Xiaolei,Kan, Weiqiu,Wang, Xiang,Hu, Huayou
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p. 413 - 420
(2016/01/28)
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- One-pot synthesis of indolizine via 1,3-dipolar cycloaddition using a sub-equivalent amount of K2Cr2O7 as an efficient oxidant under base free conditions
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A one-pot method for synthesizing multi-substituted indolizines from α-halo-carbonyl compounds, pyridines and electron deficient alkenes was developed. A sub-equivalent amount of potassium dichromate was used as an oxidant under base free conditions. The transformation developed should be of economic efficiency.
- Wang, Chao,Hu, Huayou,Xu, Juanfang,Kan, Weiqiu
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p. 41255 - 41258
(2015/05/20)
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- Synthesis and characterization of a substituted indolizine and investigation of its photoluminescence quenching via electrondeficient nitroaromatics
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Synthesis, characterization and the direct use of dimethyl 3-(4-aminophenyl)indolizine-1,2-dicarboxylate (1) as a photochemical sensor for the solution phase detection of nitroaromatics are presented. Fluorescent quenching experiments depict that nitroaro
- Bayazit, Mustafa K.,Coleman, Karl S.
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p. 362 - 371
(2014/08/05)
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- Molecular diversity of cycloaddition reactions of the functionalized pyridinium salts with 3-phenacylideneoxindoles
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The cycloaddition reactions of a series of functionalized pyridinium salts, which were generated from reaction of pyridine with active alkyl halides such as p-nitrobenzyl bromide, N,N-diethyl chloroacetamide and phenacyl bromides with 3-phenacylideneoxindoles in the presence of triethylamine showed very interesting molecular diversities. A series of the functionalized spiro[cyclopropane-1,3′-indolines], and 3-furan-3(2H)-ylidene)indolin-2- ones were successfully prepared depending upon the structures of the pyridinium salts and reaction conditions. The regioselectivity and stereoselectivity of the reactions as well as reaction mechanisms were briefly discussed.
- Fu, Qin,Yan, Chao-Guo
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supporting information
p. 5841 - 5849
(2013/07/27)
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- 'One-pot' Hammett plots: A general method for the rapid acquisition of relative rate data
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A general 'one-pot' method for determining relative rates of reaction in complex mixtures has been established using free energy relationships to demonstrate its utility. Competition experiments involving as many as seven species gave relative rate consta
- Yau, Hon Man,Harper, Jason B.,Croft, Anna K.
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supporting information
p. 8937 - 8939,3
(2020/08/31)
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- Non-thermal internal energy distribution of ions observed in an electrospray source interfaced with a sector mass spectrometer
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The internal energy distribution P(Eint) of ions emitted in an electrospray (ESI) source interfaced with a sector mass spectrometer is evaluated by using the experimental survival yield (SY) method including the kinetic shift. This method is ba
- Rondeau, David,Galland, Nicolas,Zins, Emilie-Laure,Pepe, Claude,Drahos, Laszlo,Vekey, Karoly
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experimental part
p. 100 - 111
(2011/10/05)
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- A one-pot domino reaction for the synthesis of 3-arylindolizines from pyridines, benzyl halides, and dihalide-substituted electron-deficient alkenes
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3-Arylindolizines were prepared by one-pot domino reactions from benzyl halides with pyridine (or isoquinoline) and cyclic or acyclic dihalide-substituted electron-deficient alkenes in the presence of potassium carbonate via in situ generated N-ylide intermediate. Both electron-donating and electron-withdrawing groups are tolerated in the aryl ring of benzyl halides. The yields range from moderate to high. Georg Thieme Verlag Stuttgart - New York.
- Hu, Huayou,Shi, Kunbo,Hou, Rongrong,Zhang, Zaichao,Zhu, Yulan,Zhou, Jianfeng
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experimental part
p. 4007 - 4014
(2011/02/22)
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- Synthesis of zwitterionic salts of pyridinium-meldrum acid and barbiturate through unique four-component reactions
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An efficient synthetic procedure for the preparation of the unusual charge-separated pyridinium-Meldrum acid and N,N-dimethylbarbiturate acid zwitterionic salts was developed though a unique one-pot fourcomponent reaction involving pyridine, aromatic aldehyde, Meldrum acid or N,N-dimethylbarbituric acid, and p-nitrobenzyl bromide in acetonitrile. By varying combinations of four components involving nitrogencontaining heterocycles, we conveniently established reactiveα-halomethylene compounds, aldehydes and β-dicarbonyl compounds a library of zwitterionic salts.
- Wang, Qi-Fang,Hui, Li,Hou, Hong,Yan, Chao-Guo
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supporting information; experimental part
p. 260 - 265
(2010/08/05)
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- Solvent reorganisation as the driving force for rate changes of Menschutkin reactions in an ionic liquid
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The effect on the rate of reaction of each of a series of Menschutkin processes on changing from a molecular solvent to an ionic liquid was investigated. In each case, the rate acceleration observed at room temperature could be attributed to the change in
- Yau, Hon Man,Howe, Andrew G.,Hook, James M.,Croft, Anna K.,Harper, Jason B.
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supporting information; experimental part
p. 3572 - 3575
(2010/01/06)
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- 79Br NMR spectroscopy as a practical tool for kinetic analysis
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79Br NMR spectroscopy has been used to monitor a series of reactions in which the bromide ion is produced, including the Menschutkin reaction of pyridine with a range of substituted benzyl bromides and a Heck coupling process. In cases where the process could also be monitored using 1H NMR spectroscopy, the kinetic analyses using heteronuclear magnetic resonance spectroscopy were shown to be completely consistent. Both the utility of the process in following reactions which may be difficult to analyse using other techniques and the practical limitations associated with solvent choice are discussed. Copyright
- Chan, Si Jia,Howe, Andrew G.,Hook, James M.,Harper, Jason B.
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experimental part
p. 342 - 347
(2010/02/27)
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- Reactions of N-benzyl-pyridinium or -isoquinolinium ylides with ethyl 3-fluoro-3-(fluoroalkyl)acrylates to give fluoroalkyl-substituted indolizine and pyrrolo[2,1-a]isoquinoline derivatives
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In the presence of base, N-benzylpyridinium and N-benzylisoquinolinium ylides generated in situ from the N-benzyl-pyridinium or -isoquinolinium bromides react with ethyl 3-fluoro-3-fluoroalkyl(except bromodifluoromethyl)acrylates to give one or two fluoro
- Peng, Weimin,Zhu, Shizheng
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p. 3204 - 3210
(2007/10/03)
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- EFFECTS OF SUBSTITUENTS IN THE BENZYL BROMIDE ON THE KINETICS OF THE BENZYLATION OF AMINES
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The kinetics of the reactions of 3- and 4-substituted benzyl bromides with amines having various structures in nitrobenzene at 40 deg C were investigated.The 4-substituted benzyl bromides have higher reactivity compared with that calculated on the basis of the linear correlations according to the Hammett-Taft equation for unsubstituted and 3-substituted benzyl bromides containing electron-withdrawning substituents.The reactivity of benzyl bromides containing electron-donating substituents obeys a linear correlation with the ?+ constants.The effects of structural changes in the substrate and the nucleophile on the character of the transition states of the investigated reactions is discussed.
- Shpan'ko, I. V.,Korostylev, A. P.,Rusu, L. N.
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p. 1715 - 1723
(2007/10/02)
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