- “On water” nano-Cu2O-catalyzed CO-free one-pot multicomponent cascade cyanation-annulation-aminolysis reaction toward phthalimides
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An efficient nano-Cu2O-catalyzed cascade multicomponent reaction of 2-halobenzoic acids and trimethylsilyl cyanide with diverse amines was developed using water as a solvent, affording versatileN-substituted phthalimide derivatives in moderate to excellent yields. This novel strategy features carbon monoxide gas-free, environmentally benign, one-pot multistep transformation, commercially available reagents, a cheap catalyst without any additives, wide functional group tolerance, and operational convenience.
- Wen, Xiaowei,Liu, Xiaojuan,Yang, Zhiqi,Xie, Menglan,Liu, Yuxi,Long, Lipeng,Chen, Zhengwang
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supporting information
p. 1738 - 1743
(2021/03/14)
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- Photochemical Decarboxylative C(sp3)-X Coupling Facilitated by Weak Interaction of N-Heterocyclic Carbene
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While N-hydroxyphthalimide (NHPI) ester has emerged as a powerful reagent as an alkyl radical source for a variety of C-C bond formations, the corresponding C(sp3)-N bond formation is still in its infancy. We demonstrate herein transition-metal-free decarboxylative C(sp3)-X bond formation enabled by the photochemical activity of the NHPI ester-NaI-NHC complex, giving primary C(sp3)-(N)phth, secondary C(sp3)-I, or tertiary C(sp3)-(meta C)phth coupling products. The primary C(sp3)-(N)phth coupling offers convenient access to primary amines.
- Chen, Kun-Quan,Wang, Zhi-Xiang,Chen, Xiang-Yu
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p. 8059 - 8064
(2020/11/02)
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- Method for constructing N-isobutylphthalimide in one step by using imine as starting material
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The invention discloses a method for constructing N-isobutylphthalimide in one step by using imine as a starting material. According to the method, (E)-N-isobutyl-1-phenylmethylenimine is used as a reaction raw material and subjected to a carbonylation reaction to construct N-isobutylphthalimide in one step. The method has the characteristics of mild reaction conditions, simple operation procedures and excellent yield.
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Paragraph 0022; 0023; 0024; 0035; 0036; 0037; 0038; 0041
(2019/01/24)
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- Carbonylation Access to Phthalimides Using Self-Sufficient Directing Group and Nucleophile
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Herein we report a novel palladium-catalyzed oxidative carbonylation reaction for the synthesis of phthalimides with high atom- and step-economy. In our strategy, the imine and H2O, which are generated in situ from the condensation of aldehyde and amine, serve as self-sufficient directing group and nucleophile, respectively. This method provides rapid access to phthalimides starting from readily available materials in a one-pot manner. Various phthalimide derivatives are constructed efficiently, including medicinally and biologically active phthalimide-containing compounds.
- Ji, Fanghua,Li, Jianxiao,Li, Xianwei,Guo, Wei,Wu, Wanqing,Jiang, Huanfeng
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p. 104 - 112
(2018/02/19)
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- Photoinduced, Copper-Catalyzed Decarboxylative C-N Coupling to Generate Protected Amines: An Alternative to the Curtius Rearrangement
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The Curtius rearrangement is a classic, powerful method for converting carboxylic acids into protected amines, but its widespread use is impeded by safety issues (the need to handle azides). We have developed an alternative to the Curtius rearrangement that employs a copper catalyst in combination with blue-LED irradiation to achieve the decarboxylative coupling of aliphatic carboxylic acid derivatives (specifically, readily available N-hydroxyphthalimide esters) to afford protected amines under mild conditions. This C-N bond-forming process is compatible with a wide array of functional groups, including an alcohol, aldehyde, epoxide, indole, nitroalkane, and sulfide. Control reactions and mechanistic studies are consistent with the hypothesis that copper species are engaged in both the photochemistry and the key bond-forming step, which occurs through out-of-cage coupling of an alkyl radical.
- Zhao, Wei,Wurz, Ryan P.,Peters, Jonas C.,Fu, Gregory C.
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supporting information
p. 12153 - 12156
(2017/09/12)
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- Metal-free C-N cross-coupling of electrophilic compounds and N-haloimides
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When DBU is added, the cross-coupling reaction between alkyl halides (halogen = Cl, Br and I) and N-haloimides (halogen = Cl, Br) occurs, resulting in the formation of aminated products. A halogen bond activated nucleophilic substitution mechanism was proposed. The methodology represents an elegant example of applying the halogen bond activation strategy in an organic transformation.
- Zhang, Luyan,Li, Yanru,Jin, Long-Yi,Liang, Fushun
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p. 65600 - 65603
(2015/08/18)
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- A metal-free approach for transamidation of amides with amines in aqueous media
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An efficient, environmentally benign and a mild protocol for transamidation of amides with a variety of amines in the presence of K2S2O8 using stoichiometric quantity in aqueous conditions has been established. This method works under conventional thermal conditions and in microwave irradiation as well. A series of amides have been prepared using this reaction and this is a greener protocol for transamidation, which offers a diverse kind of substrate scope with exclusive product formation (yields 90-98%).
- Srinivas, Mahesuni,Hudwekar, Abhinandan D.,Venkateswarlu, Vunnam,Reddy, G. Lakshma,Kumar, K. A. Aravinda,Vishwakarma, Ram A.,Sawant, Sanghapal D.
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supporting information
p. 4775 - 4779
(2015/07/20)
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- The potential of methylsiloxanes as solvents for synthetic chemistry applications
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The potential use of volatile methylsiloxanes (VMSs) as solvents for chemicals synthesis has been explored. Assessment of the environmental impact of these VMS solvents is made and found to be significantly lower than those of the non-polar organic solvents that they have the potential to replace. The polarities of the VMSs, as expressed by empirical polarity measurements, and miscibilities with other liquids are found to be similar to those of alkane solvents. Finally, some uses of VMSs as solvents for both organic and inorganic transformations are described. The VMSs provide environmentally more sustainable (greener) alternatives to the nonpolar solvents that they have the potential to replace.
- Ab Rani, Mohd Azri,Borduas, Nadine,Colquhoun, Victoria,Hanley, Robert,Johnson, Henry,Larger, Solene,Lickiss, Paul D.,Llopis-Mestre, Veronica,Luu, Selina,Mogstad, Martin,Oczipka, Philipp,Sherwood, James R.,Welton, Tom,Xing, Jun-Yi
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p. 1282 - 1296
(2014/03/21)
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- Isoindolone derivatives, preparation process and intermediates of this process, their use as medicaments, and pharmaceutical compositions comprising them
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The present invention relates to the novel isoindolone derivatives of the formula I in which R1 to R6 have the meanings stated in the claims. The inventive compounds are suitable as antiarrhythmic medicaments with a cardioprotective component for infarction prophylaxis and infarction treatment and for the treatment of angina pectoris. They also inhibit in a preventive manner the pathophysiological processes associated with the development of ischemia-induced damage, in particular in the triggering of ischemia-induced cardiac arrhythmias and of heart failure.
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Page/Page column 13
(2008/06/13)
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- N- ((3-OXO2, 3-DIHYDRO-1H-ISOINDOL-1-YL) ACETYL) GUANIDINE DERIVATIVES AS NHE-1 INHIBITORS FOR THE TREATMENT OF INFARCTION AND ANGINA PECTORIS
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Isoindolone derivatives, preparation process and intermediates of this process, their use as medicaments, and pharmaceutical compositions comprising them. The present invention relates to the novel isoindolone derivatives of the Formula (I), in which R1 to R6 have the meanings stated in the claims. The inventive compounds are suitable as antiarrhythmic medicaments with a cardioprotective component for infarction prophylaxis and infarction treatment and for the treatment of angina pectoris. They also inhibit in a preventive manner the pathophysiological processes associated with the development of ischemia-induced damage, in particular in the triggering of ischemia-induced cardiac arrhythmias and of heart failure.
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- A facile scheme for phthalimide ? phthalimidine conversion
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Desulfurization of phenylthiolactams using an ultrasound-promoted Raney nickel protocol yields the corresponding N-substituted phthalimidines. Benzylic oxidation of the N-substituted phthalimidines by treatment with 2,2'-bipyridinium chlorochromate/m-chloroperbenzoic acid (BPCC/MCPBA) affords the original phthalimides. The reduction-desulfurization is applied to the preparation of a deoxythalidomide derivative which is a TNF-α inhibitor.
- Luzzio, Frederick A.,Piatt Zacherl, DeAnna,Figg, William D.
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p. 2087 - 2090
(2007/10/03)
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- Stereoselective Reactions of Phthalimido-Substituted Radicals Derived from (±)-Threonine: A Comparison with Reactions of N-Phthaloyliminium Ions
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Stereoselective reactions of phthalimido-substituted radicals derived from (±)-threonine with different radical traps are reported (Scheme 3, Table 1). A strong influence of the nature of the radical trap on the stereoselectivity was noticed. Small nucleophilic radical traps gave preferentially the syn products. The observed selectivities are explained with the A1.3 strain model and depend on steric and electronic effects (Fig. 2). Reactions with electrophilic radical traps such as diphenyl diselenide gave the anti diastereoisomers with moderate stereocontrol, presumably due to stereoelectronic effects. The same stereochemical outcome, i.e., preferential formation of the anti products, was observed for the reactions of the related N-phthaloyliminium ion (Scheme 5, Table 2). The stereochemistry of the ionic reaction is rationalized by a Felkin-Anh model (Fig. 3).
- Stojanovic, Aleksandar,Renaud, Philippe,Schenk, Kurt
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p. 268 - 284
(2007/10/03)
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- Solvent free N-alkyl and N-arylimides preparation from anhydrides catalyzed by TaCl5-silica gel
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The first Lewis acid catalyzed and solvent free procedure for the preparation of imides from the corresponding anhydrides is described involving TaCl5-silica gel as Lewis acid under microwave irradiation.
- Chandrasekhar,Takhi, Mohamed,Uma
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p. 8089 - 8092
(2007/10/03)
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- Photodecarboxylation of N-Phthaloyl-α-amino Acids
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N-Phthaloylglycine (1a) was irradiated with a high pressure mercury lamp to give N-methylphthalimide (2a) in an excellent yield.N-Phthaloyl derivatives 1b-k of other α-amino acids also afforded the decarboxylated products 2b-k.In the cases of N-phthaloylserine (11) and di-phthloylcystine (1m), N-vinylphthalimide (3) was isolated as a major product.On the other hand, N-phthaloylmethionine (11a) and methyl N-phthaloylmethionate (11b) were treated in the same manner to give the aza-thiacyclo-heptanol derivatives 12a-b having a new ring system.Solvent effects and possible pathways of these reactions were examined.Keywords- N-phthaloyl-α-amino acid; photolysis; decarboxylation; cyclization; efficiency; solvent effect; υ-hydrogen abstraction
- Sato, Yasuhiko,Nakai, Hideo,Mizoguchi, Tomishige,Kawanishi, Masazumi,Hatanaka, Yasumaru,Kanaoka, Yuichi
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p. 1263 - 1270
(2007/10/02)
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